RU2574591C2 - Indanone derivative, its pharmaceutically acceptable salt or enantiomer, method for producing it and pharmaceutical composition containing it and applicable for preventing or treating viral disease - Google Patents

Abstract

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new indanone derivatives of formula I

wherein the radicals A¹-A⁴, D, E, X and G¹-G⁴ have the values specified in the description, to their pharmaceutically acceptable salts or enantiomers, as well as to methods for producing them, and a pharmaceutical composition applicable for preventing and treating a viral disease and containing the above compounds as an active ingredient.

EFFECT: indanone derivatives possess the excellent inhibitory activity on picornaviruses, including Coxsackie viruses, entero-, echo-, polio- and rhinoviruses; it also possesses low cytotoxicity, and can be effective as an active ingredient of the pharmaceutical composition for preventing or treating a viral disease, including poliomyelitis, paralysis, acute haemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular fever, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, influenza, Coxsackie virus A disease, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.

17 cl, 5 tbl, 307 ex

Description

Technical field

The present invention relates to indanone derivatives, to their pharmaceutically acceptable salts or enantiomers, to methods for their preparation and to pharmaceutical compositions containing them for the prevention and treatment of viral disease.

State of the art

Picornaviruses are non-envelope positive single-stranded RNA viruses whose genomic RNA is 7.2-8.5 kb in length. These viruses are very small and have a globular size of approximately 22-30 nm, and were first identified a very long time ago. Among viruses belonging to the Picornaviridae family, enteroviruses are isolated, including rhinovirus, poliovirus, coxsackie A virus, coxsackie B virus and echovirus and hepatitis A virus.

The diseases caused by picornaviruses range from respiratory diseases to intestinal diseases, from circulatory diseases to skin diseases, examples of which include poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus, hepatitis A, myositis , myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, vesicular pharyngitis and foot and mouth disease. However, there are no therapeutic agents to treat these diseases. Most of the drugs under development are decapsidation inhibitors. Viruses belonging to the Picornaviridae family cause various diseases, including the above respiratory diseases, which cause hygienic, social and economic problems. Picornaviruses are the main causative factors of waterborne diseases. Being extremely stable and difficult to disinfect, RNA viruses constantly cause the corresponding diseases.

Human rhinoviruses (hRV) have recently been associated with a large number of cases of exacerbation of asthma, and it is known that they are present even in the bronchial tissue of most asthma patients in the stable remission phase. Comparison of the corresponding biopsy samples of the bronchial mucosa taken from patients with asthma and patients without asthma showed a significantly higher frequency of detection of human rhinoviruses in the lower respiratory tract in patients with asthma compared with patients without asthma. A correlation has also been reported between the presence of human rhinovirus and the clinical severity of asthma. In addition, rhinoviruses cause chronic obstructive pulmonary disease, pneumonia, sinusitis and otitis media, as well as asthma.

Rhinoviruses are the main cause of colds, and diseases that are caused by enterovirus include meningitis, respiratory tract infection, and the like. Large-scale poliovirus vaccination efforts have significantly reduced the incidence of poliomyelitis worldwide, but cases are still reported in Niger, Nigeria, Egypt, India, Pakistan and Afghanistan. Hepatitis A can now be controlled to some extent due to the presence of hepatitis A vaccines. However, vaccines against coxsackie viruses, echoviruses or rhinoviruses have not yet been developed.

In particular, the Coxsackie B virus is the main causative agent of myocarditis, which can develop in severe cases before idiopathic dilated cardiomyopathy, which requires heart transplantation.

Derivatives of enviroxim are considered the most promising candidates with broad anti-enterovirus and antirinovirus activity. Enviroxime inhibits the synthesis of the “plus” RNA chain by binding to the 3A viral protein necessary for the formation of intermediate RNAs during virus reproduction (Heinz B.A. and Vance L.M .: J Virol, 1995, 69 (7), 4189-97). In clinical studies, however, insignificant effects of the compound or their small number were observed with the concomitant detection of poor pharmacokinetics and undesirable side effects (Miller F.D. et al .: Antimicrob Agents Chemother, 1985, 27 (1), 102-6).

AG 7088 protease inhibitor was developed based on knowledge of the fine structure and function of viral protease 2C. In a cell culture with a nanomolar concentration range, inhibitor A 7088 had an effect against rhinovirus type 48 and coxsackie virus A21, B3, enterovirus 70 and echovirus 11 (Pattick AK et al .: Antimicrobila Agents Chemother, 1999, 43 (10), 2444-50) .

By elucidating the molecular structure of viral capsids, prerequisites were obtained for the targeted creation of capsid blockers, “WIN substances” (Diana G. D .: Curr Med Chem 2003, 2, 1-12). They inhibit the adsorption and / or decapsidation of rhinoviruses and enteroviruses. Some of the substances WIN have a very specific effect only in relation to certain genera or viral types of picornavirus. Other derivatives inhibit the replication of both rhinovirus and enteroviruses. WIN substances, for example, include aryldon, disoxaryl, and pyrodavir. These compounds show very strong antiviral effects in cell culture. However, poor solubility (aryldon), low bioavailability (aryldon and disoxaril), rapid metabolism and excretion (disoxaril and WIN 54954), as well as side effects such as skin rashes (WIN 54954), make their clinical use impossible.

Pleconaril, a type of WIN, has very good oral bioavailability and, after binding to a hydrophobic pocket in a virus capsid, it inhibits the penetration of rhino, echoviruses and Coxsacka viruses (Pevear DC et al .: Antimicrob Agents Chemother 1999, 43 (9), 2109 -15; McKinlay MA et al .: Annu Rev Microbiol 1992, 46, 635-54). Thus, pleconaril is potentially effective against a wide range of viral diseases ranging from colds to viral meningitis or myocarditis. Resistance to it was noted for rhinoviruses, enterovirus 71 and Coxsackie B3 virus (Ledford RM et al .: J Virol 2004, 78 (7), 3663-74; Groarke JM et al .: J Infect Dis 1999, 179 (6), 1538-41). However, the proven therapeutic effect was not sufficient to register pleconaril (Picovir, ViroPharma, USA) as a treatment for rhinovirus infections in the USA. In March 2002, a request was rejected by the Food and Drug Administration (FDA) because the therapeutic benefits were very low and side effects were observed.

It was found that BTA-798 has a higher antiviral activity compared to pleconaril, according to in vitro and in vivo analyzes with rhinoviruses, and is currently undergoing clinical trials (Ryan, J. et al. Antiviral Res [18 ^th Intl Conf Antiviral Res (April 11-14, Barcelona) 2005] 2005, 65 (3): Abst LB-11).

However, no antiviral drugs have yet been developed that are approved for use in the treatment of entero-or rhinoviruses.

Intensive and thorough studies of effective virostatic agents against picornaviruses, including Coxsackie, entero-, echo-, polio- and rhinoviruses, which led to the creation of the present invention, culminated in the fact that indanone derivatives were found to have high inhibitory activity against picornaviruses, including coxsackie viruses, entero-, echo-, polio- and rhinoviruses.

Description

Technical challenge

Thus, the aim of the present invention is to provide a new derivative of indanone or its pharmaceutically acceptable salt or its enantiomer.

Another object of the present invention is to provide a process for preparing a derivative of indanone or a pharmaceutically acceptable salt thereof or its enantiomer.

Another objective of the present invention is to provide a pharmaceutical composition for the prophylaxis or treatment of a viral disease, comprising an indanone derivative or a pharmaceutically acceptable salt thereof or its enantiomer as an active ingredient.

Technical solution

In accordance with one aspect, the present invention provides an indanone derivative represented by the following chemical formula 1, a pharmaceutically acceptable salt thereof, or an enantiomer thereof:

[Chemical formula 1]

(Where

A ¹ , A ² , A ³ , A ⁴ , D, E, Z, G ¹ , G ² , G ³ , G ⁴ , X and Y are as defined respectively in the description below.)

In accordance with another aspect, the present invention provides a process for the preparation of an indanone derivative, pharmaceutically acceptable salt or enantiomer.

In accordance with another aspect, the present invention provides a pharmaceutical composition for the prophylaxis or treatment of a viral disease, comprising an indanone derivative, a pharmaceutically acceptable salt or enantiomer as an active ingredient.

Advantages of the Invention

Due to its excellent inhibitory activity against picornaviruses, including Coxsackie viruses, entero-, echo-, polio- and rhinoviruses, as well as low cytotoxicity, the indanone derivative of chemical formula 1 can be used as an active ingredient in a pharmaceutical composition for the prevention or treatment of viral disease, including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epi Demial myalgia, encephalitis, influenza, vesicular pharyngitis, foot and mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.

Best option exercise

The following is a detailed description of the present invention.

In accordance with one aspect, the present invention provides an indanone derivative represented by the following chemical formula 1, a pharmaceutically acceptable salt thereof or an optical isomer thereof:

[Chemical formula 1]

,

,

Where

A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of —H, halogen, —OH, —CN, —N ₃ , C ₁ –C ₁₀ alkoxy, linear or branched C ₁ –C ₁₀ alkyl unsubstituted or substituted with -OH or methoxyphenylalkyl of 5-7 membered heterocycloalkyl, C ₆ -C ₁₂ aryl, -O (C = O) R ¹ , - (C = O) R ¹ , - (C = O) OR ¹ , -O (C = O) OR ¹ , -O (C = O) NR ¹ R ² , -NO ₂ , -NR ¹ R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = S) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (C = O) NR ² R ³ , -NR ¹ (SO ₂ ) R ² and -NR ¹ (C = S) NR ² R ³ , two or more adjacent substituents of A ¹ , A ² , A ^3, and A ⁴ together may form a ring;

D is —OH, halogen, linear or branched C ₁ -C ₁₀ alkyl unsubstituted or substituted with phenyl C ₁ -C ₁₀ alkoxy, —O (CH ₂ ) _n OH, —O (C = O) R ¹ , - ( C = O) R ¹ , - (C = O) OR ¹ , -O (C = O) OR ¹ , -O (C = O) NR ¹ R ² , -NO ₂ , -NR ¹ R ² , -NR ¹ (O) R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = S) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (C = O) NR ¹ R ² or -NR ¹ (C = S) NR ¹ R ² ;

;E represents halogen, -OH, -CN, -N = C = O, -N ₃ , C ₁ -C ₁₀ alkoxy, -O (C = O) R ¹ , - (C = O) R ¹ , - ( C = O) OR ¹ , -O (C = O) OR ¹ , -O (C = O) NR ¹ R ² , -NO ₂ , -NR ¹ R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = S) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (C = O) NR ¹ R ² , -NR ¹ (C = O) NR ² OR ³ , -NR ¹ (SO ₂ ) R ² , -NR ¹ (C = S) NR ¹ R ² , -NR ¹ (P = O) (OR ² ) ₂ or

;

G ¹ , G ² , G ³ and G ^{4 are} independently or optionally selected from the group consisting of —H, halogen, —OH, CN, C ₁ -C ₁₀ alkoxy, linear or branched C ₁ -C ₂₀ alkyl, C ₆ - C ₁₂ aryl, -O (C = O) R ¹ , - (C = O) R ¹ , - (C = O) OR ¹ , - (CH ₂ ) _n - (C = O) OR ¹ , -O ( C = O) OR ¹ , -O (C = O) NR ¹ R ² , -NO ₂ , -NR ¹ R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = S) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (C = O) NR ² R ³ and -NR ¹ (C = S) NR ² R ³ , provided that at least two or more adjacent substituents from G ¹ , G ² , G ³ and G ⁴ together may form a ring;

X represents hydrogen, oxygen, sulfur, hydroxy, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkylene, = N-NR ¹ R ² , -NR ¹ -OR ² or = N-OR ¹ ;

Y represents —O—, —CH ₂ -, —NH— or - (NR ⁵ ) -;

R ⁵ represents - (C = O) H, - (C = O) OH, - (C = O) R ¹ , - (C = S) R ¹ or - (C = O) OR ¹ ;

Z represents C or N;

R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkenyl, unsubstituted or substituted by phenyl, C ₃ -C ₇ cycloalkyl, C ₃ -C ₇ heterocycloalkyl, C ₆ -C ₁₂ aryl or 5-14 membered heteroaryl;

where heterocycloalkyl may be substituted by one or more oxygen atoms via a double bond,

aryl is mono- or bicyclic and may have one or more substituents selected from the group consisting of halogen, —CN, phenyl, linear or branched C ₁ -C ₆ alkyl, R ⁵ and C ₁ -C ₆ alkoxy,

heteroaryl is mono-, bi- or tricyclic and may have one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, ═O or —O—, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,

linear or branched alkyl may be unsubstituted or substituted by one or more substituents selected from the group consisting of phenyl, halogen, 5-7 membered heteroaryl and —NHBoc,

phenyl may be substituted with one or more substituents selected from the group consisting of halogen, phenyl or phenyl-substituted C ₁ -C ₆ alkoxy,

heterocycloalkyl or heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S,

halogen is F, Cl, Br or I,

n is an integer from 1 to 10, and

′ обозначает одинарную или двойную связь.′

′ Denotes a single or double bond.

In a preferred embodiment

A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of -H, C ₁ -C ₅ alkoxy, linear or branched C ₁ -C ₅ alkyl, unsubstituted or substituted with -OH or methoxyphenylalkyl 5-7 heterocycloalkyl membered, C ₆ -C ₁₂ aryl, -NO ₂ and -NR ¹ R ² ;

D is —OH, halogen, linear or branched C ₁ -C ₅ alkyl or unsubstituted or substituted with phenyl C ₁ -C ₅ alkoxy;

E is halogen, —OH, C ₁ -C ₅ alkoxy, —NR ¹ (C = O) R ² , —NR ¹ (C = O) OR ² or —NR ¹ (C = O) NR ¹ R ² ;

G ¹ , G ² , G ^3, and G ^{4 are} independently or optionally selected from the group consisting of —H, C ₁ -C ₅ alkoxy and linear or branched C ₁ -C ₁₆ alkyl;

X represents oxygen, hydroxyl or linear or branched C ₁ -C ₅ alkyl;

Y represents —O— or —CH ₂ -;

Z represents C or N;

R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen, linear or branched C ₁ -C ₇ alkyl, C ₃ -C ₇ heterocycloalkyl, C ₆ -C ₁₂ aryl or 5-14 membered heteroaryl;

where heterocycloalkyl may be substituted by one or more oxygen atoms via a double bond,

aryl is mono- or bicyclic and may have one or more substituents selected from the group consisting of halogen, phenyl, linear or branched C ₁ -C ₃ alkyl and C ₁ -C ₃ alkoxy,

heteroaryl is mono-, bi- or tricyclic and may have one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, ═O or —O—, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,

linear or branched alkyl may be unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, halogen and 5-7 membered heteroaryl,

phenyl may be substituted with one or more substituents selected from the group consisting of halogen and phenyl,

heterocycloalkyl or heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S,

halogen is F or Cl, and

′ обозначает одинарную или двойную связь.′

′ Denotes a single or double bond.

In a more preferred embodiment

A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of —H and —NR ¹ R ² ;

D represents —OH;

E represents —OH or —NR ¹ (C = O) R ² ;

G ¹ , G ² , G ³ and G ⁴ independently or optionally are linear or branched C ₁ -C ₁₅ alkyl;

X represents oxygen;

Y represents —O—;

Z represents C;

R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or 5-14 membered heteroaryl;

wherein the 5-14 membered heteroaryl is monocyclic, bicyclic or tricyclic and may be substituted with one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, ═O or —O— linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,

phenyl may be substituted by one or more substituents selected from the group consisting of halogen and phenyl,

heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S, and

halogen is F or Cl, and

′ обозначает одинарную или двойную связь.′

′ Denotes a single or double bond.

In a further, even more preferred embodiment

A ¹ , A ² and A ³ are —H, and A ⁴ is —NH ₂ ;

D represents —OH;

E represents —NR ¹ (C = O) R ₂ ;

G ¹ , G ³ and G ⁴ represent —H, and G ² represents isopropyl;

X represents oxygen;

Y represents —O—;

Z represents C;

R ¹ represents hydrogen, and R ² represents a 5-14 membered heteroaryl;

where heteroaryl is furan, benzofuran, pyridine, pyrazolopyridine, pyrimidine, pyrazolopyrimidine, pyrazine, thiophene, quinoline, isoquinoline, triazole, thiazole, indole, pyrazole, indazole, tetrazole, benzotriazole, chromene, pyranesole, pyrrole, pyrozole, pyrrole cinnoline, imidazole, benzoimidazole, acridine, imidazopyridine, imidazopyrimidine, quinoxaline, pyridazine, tetrazolopiridin, triazolopyridine, triazolopyrimidine, or indolizine and may be substituted with one or more substituents selected from the group consisting of halogen, -OH, -NO _2, -NH ₂ , —CN, ═O or —O—, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl, and

halogen is F or Cl, and

обозначает двойную связь.

denotes a double bond.

Specific examples of the compound represented by chemical formula 1 include:

1) 4b, 9b-dihydroxy-7-methyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

2) 7-methyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;

3) ethyl 2- (4b, 9b-dihydroxy-6-methoxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-8-yl) acetate;

4) 4b, 9b-dihydroxy-7,8-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

5) 4b, 9b-dihydroxy-4b, 9b-dihydro-10H-indeno [1,2-b] benzofuran-10-one;

6) 8-fluoro-4b, 9b-dihydroxy-4b, 9b-dihydro-10H-indeno [1,2-b] benzofuran-10-one;

7) 4b, 9b-dihydroxy-7-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

8) 6,7-dichloro-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

9) 7-ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

10) 4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

11) 7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;

12) 4b, 9b-dihydroxy-8-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

13) 4b, 9b-dihydroxy-6-phenyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

14) 4b, 9b-dihydroxy-8-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

15) 4b, 11b-dihydroxy-4bH-indeno [1,2-b] naphtho [2,3-d] furan-12 (11bH) -one;

16) 6b, 11b-dihydroxy-6bH-indeno [1,2-b] naphtho [2,1-d] furan-7 (11bH) -one;

17) 4b, 9b-dihydroxy-8-propyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

18) 8-ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

19) 8-sec-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

20) 8-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

21) 6-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

22) 4b, 9b-dihydroxy-7,8,9-trimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

23) 4b, 9b-dihydroxy-8-tert-pentyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

24) 6,8-di-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

25) 6,8-di-tert-butyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;

26) 4b, 9b-dihydroxy-8-nonyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

27) 4b, 9b-dihydroxy-8-pentadecyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

28) 6.8-bis- (1,1-dimethylpropyl) -4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

29) isopropyl-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;

30) 5a, 10a-dihydroxy-2,3,5a, 10a-tetrahydro-diindeno [1,2-b: 5 ′, 6′-d] furan-10 (1H) -one;

31) 6b, 11b-dihydroxy-1,2,3,4,6b, 11b-hexahydro-12-oxa-benzo [4,5] pentaleno [2,1-a] naphthalen-7-one;

32) 4b, 9b-dihydroxy-7-isopropyl-2-methoxy-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;

33) 7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis (2,2-dimethylpropanoate);

34) (2E, 2′E) -7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis (3- phenylacrylate);

35) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylacrylate;

36) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno-b] furan-4b-yl-furan-2-carboxylatefuran-2-carboxylic acid;

37) diethyl-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl dicarbonate;

38) ethyl 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate;

39) methyl 4b, 9b-dihydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-8-carboxylate;

40) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yldiethylcarbamate;

41) 4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yldiethylcarbamate;

42) 2,3-difluoro-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

43) 1,4b, 9b-trihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

44) 4b, 9b-dihydroxy-7-isopropyl-1H-cyclopenta [b] naphthalene [1,2-b] furan-10 (9bH) -one;

45) 9b-hydroxy-7-isopropyl-4b-methoxy-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

46) 1-amino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

47) 1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;

48) N- (4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide;

49) methyl 4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;

50) 1-amino-7-ethyl-4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

51) 7-ethyl-4b, 9b-dihydroxy-1-nitro-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;

52) 7-ethyl-2,4b, 9b-trihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

53) 4b-acetoxy-1-amino-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;

54) 4b-acetoxy-7-isopropyl-1-methanesulfonylamino-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;

55) 1- (4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) -3-isopropylurea;

56) N- (9b-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide;

57) N, N ′ - (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1,9b-diyl) diacetamide;

58) N- (7-amino-2-hydroxy-2- (4-isopropyl-2-hydroxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-4-yl) acetamide;

59) N- (2-amino-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide ;

60) 1-amino-4b, 9b-dihydroxy-7-isopropyl-2-nitro-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

61) 1,4-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

62) 1,2-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

63) 2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-yldimethylcarbamate;

64) 4b, 9b-dihydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

65) 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

66) N- (4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) acetamide;

67) 9b-hexylamino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

68) 9b-amino-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

69) 4b-hydroxy-9b-isocyanato-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;

70) methyl - ((4b, 9b) -4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-9bH-indeno [1,2-b] benzofuran-9b-yl) carbamate;

71) (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) pentanoic acid amide;

72) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) isobutylamide;

73) N- (1-amino-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide;

74) N- (9b-hydroxy-6,8-diisopropyl-10-oxo-9b, 10-dihydro-5-oxa-indeno [2,1-a] inden-4b-yl) acetamide;

75) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) -N-methylacetamide;

76) 1- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) -3-isopropylurea;

77) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) isobutylamide;

78) (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) pentanoic acid amide;

79) 9b-hydroxy-4b- (2-hydroxyethoxy) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

80) 4b, 9b-dihydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

81) 4b, 9b-dihydroxy-7-isopropyl-2,3-dimethoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

82) 4b, 9b-dihydroxy-7-isopropyl-2,3-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

83) a mixture of 6: 4 (4bS, 9bS) -2-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one and

(4bS, 9bS) -3-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

84) indeno [2,1-a] inden-4b, 9b (5H, 10H) -diol;

85) isopropyl- (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate;

86) ethyl (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate;

87) N, N ′ - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1, 9b-diyl) diacetamide;

88) O-methyloxy 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

89) 9b-butyrylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of butyric acid;

90) [2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxoindan-2-yl] octanoic acid amide;

91) 9b-hexanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl hexanoic acid ester;

92) 9b-heptanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl heptanoic acid ester;

93) N - ((4bS, 9bS) -1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) octanamide ;

94) (4bR, 9bS) -1-amino-7-isopropyl-10-oxo-9b-propionamido-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpropionate;

95) (4bR, 9bS) -1-amino-9b-butyramido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylbutyrate;

96) 1-amino-7-isopropyl-10-oxo-9b-pentanamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpentanoate;

97) 1-amino-9b-hexanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylhexanoate;

98) (4bS, 9bS) -4b-hydroxy-7-isopropyl-9b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

99) 1-amino-9b-heptanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylheptanoate;

100) 1 - ((4bS, 9bS) -7-isopropyl-4b-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea;

101) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylurea;

102) 1-ethyl-3 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea ;

103) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxyurea;

104) 5-acetyl-4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;

105) 4b, 9b-dihydroxy-7,8-dimethyl-5-propionyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;

106) 4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;

107) 5-acetyl-7.8-dimethyl-10-oxo-4b, 5.9b, 10-tetrahydroindeno [1,2-b] indole-4b, 9b-diyl diacetate;

108) 5-acetyl-9b-amino-4b-hydroxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;

109) N- (9b-amino-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl) acetamide ;

110) 1.9b-bis-acetylamino-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl acetic acid ester;

111) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;

112) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpentanoate;

113) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;

114) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) pivalamide;

115) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylbutyl carbonate;

116) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl-ethyl carbonate;

117) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl pivalate;

118) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylmethylcarbamate;

119) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) diacetamide;

120) 4b- (benzyloxy) -9b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

121) 9b-acetylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of phenyl carbonic ester;

122) O- (9b-azido-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) phenylthiocarbamic acid ester;

123) ethyl 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate;

124) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) dipropionamide;

125) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) bis (2-methylpropanamide);

126) 4b, 9b-dihydroxy-7-isopropyl-4bH-benzofuro [2 ′, 3 ′: 3,4] cyclopenta [1,2-b] pyridin-10 (9bH) -one;

127) 10-hydroxy-7-isopropyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl diacetate;

128) O-methyloxyxim of 9b-hydroxy-7-isopropyl-4b- (methoxyamino) -4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

129) 7-isopropyl-4b-methoxy-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-ol;

130) O-methyloxime of 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

131) a mixture of 1-bromo and 4-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

132) 1- (benzylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

133) 1- (ethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

134) 9b-hydroxy-7-isopropyl-4b-methyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;

135) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;

136) 7-isopropyl-10-methyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diol;

137) N- (1-bromo-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide;

138) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethoxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;

139) 4b, 9b-dihydroxy-7-isopropyl-2-piperidinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

140) 4b, 9b-dihydroxy-7-isopropyl-2-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

141) 4b, 9b-dihydroxy-7-isopropyl-1-piperidinyl-4bH-benzo [d] indeno- [1,2-b] furan-10 (9bH) -one;

142) 4b, 9b-dihydroxy-7-isopropyl-1-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

143) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) propionamide;

144) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) butyramide;

145) 4b, 9b-dihydroxy-5-isobutyryl-7-isopropyl-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;

146) 4b, 9b-dihydroxy-7-isopropyl-2- (hydroxypiperidinyl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

147) 4b, 9b-dihydroxy-1- (4-hydroxypiperidin-1-yl) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

148) 4b, 9b-dihydroxy-7-isopropyl-2- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - it;

149) 4b, 9b-dihydroxy-7-isopropyl-1- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - it;

150) 2- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

151) 1- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

152) 10-hydrazono-7-isopropyl-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diol;

153) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide;

154) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxybenzamide;

155) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chlorobenzamide;

156) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-nitrobenzamide;

157) 1-amino-4b, 9b-dihydroxy-6,8-diisopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;

158) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) cyclopropanecarboxamide;

159) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (4-methoxyphenyl) thiourea;

160) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (phenyl) thiourea;

161) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) thiophene-2-carboxamide;

162) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-methoxyphenyl )urea;

163) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-butylurea;

164) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-fluorophenyl )urea;

165) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (tert-butyl )urea;

166) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;

167) N- (1-formamido-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide;

168) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;

169) diethyl- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) phosphoamidate;

170) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-cyanobenzamide;

171) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-naphthamide;

172) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - [1,1′- biphenyl] -4-carboxamide;

173) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- ethylurea;

174) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) tetrahydrofuran-2 β-carboxamide;

175) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,2,2- trifluoroacetamide;

176) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1, 1,1-trifluoromethanesulfonamide;

177) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;

178) 1,1,1-trifluoro-N- (4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;

179) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-phenylacetamide;

180) (E) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (3,4-dichlorophenyl) acrylamide;

181) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4- (benzyloxy) benzamide ;

182) 2 - ([1,1′-biphenyl] -4-yl) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) acetamide;

183) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxybenzamide;

184) tert-butyl (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) -1-oxopropan-2-ylcarbamate;

185) tert-butyl (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) -1-oxo-3-phenylpropan-2-ylcarbamate;

186) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- methylbenzamide;

187) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzamide;

188) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methylbenzamide;

189) methyl 4- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamoyl) benzoate ;

190) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chlorobenzamide;

191) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3,5-dimethylbenzamide;

192) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,4,6- trichlorobenzamide;

193) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- fluoroacetamide;

194) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- chloroacetamide;

195) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2, 2-dichloroacetamide;

196) 1-amino-9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 ( 9bH) -one;

197) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;

198) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;

199) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isonicotinamide;

200) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazine-2-carboxamide;

201) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;

202) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide;

203) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide;

204) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran-2 β-carboxamide;

205) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzofuran-2-carboxamide;

206) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylthiazole-5- carboxamide;

207) (4R) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2- oxothiazolidine-4-carboxamide;

208) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-2-carboxamide;

209) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-3-carboxamide;

210) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;

211) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-phenyl-5- (trifluoromethyl) - 1H-pyrazole-4-carboxamide;

212) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indazole-3-carboxamide;

213) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazol-1-yl) acetamide;

214) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-3-carboxamide;

215) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide;

216) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylthiophen-2- carboxamide;

217) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxythiophen-3- carboxamide;

218) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;

219) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrimidine-4-carboxamide;

220) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazole -5-yl) acetamide;

221) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] [1,2,3] triazole-5-carboxamide;

222) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-1,2, 4-triazole-3-carboxamide;

223) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5-nitrothiophen-2- carboxamide;

224) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2,6-dioxo 1,2,3,6-tetrahydropyrimidine-4-carboxamide;

225) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- chromene-3-carboxamide;

226) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- pyran-5-carboxamide;

227) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;

228) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (2-chloro -6-fluorophenyl) -5-methylisoxazole-4-carboxamide;

229) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-phenyl-1H-pyrazol-5- carboxamide;

230) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;

231) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-oxo-2- (thiophen-2-yl) acetamide;

232) 5-amino-N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2 β-carboxamide;

233) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2- carboxamide;

234) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxyisonicotinamide;

235) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b ] thiophene-2-carboxamide;

236) 3- (2,6-dichlorophenyl) -N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) -5-methylisoxazole-4-carboxamide;

237) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -9H- xanthene-9-carboxamide;

238) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4 β-carboxamide;

239) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4-carboxamide;

240) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-5-carboxamide;

241) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridin-9 β-carboxamide;

242) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- nitro-1H-pyrazole-3-carboxamide;

243) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methyl picolinamide;

244) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- (trifluoromethyl) picolinamide;

245) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5- cyanopicolinamide;

246) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- chloropicolinamide;

247) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methoxyquinoline-2-carboxamide;

248) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isoquinoline-3-carboxamide;

249) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methylisonicotinamide;

250) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-fluoroisonicotinamide;

251) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloroisonicotinamide;

252) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-2-carboxamide;

253) 2 - ((1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1-oxide ;

254) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chloronicotinamide;

255) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-nicotinamide;

256) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-hydroxynicotinamide;

257) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-hydroxypicolinamide;

258) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylnicotinamide;

259) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylnicotinamide;

260) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;

261) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methoxynicotinamide;

262) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide ;

263) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinolin-2 β-carboxamide;

264) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- bromobenzo [b] thiophene-2-carboxamide;

265) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indole-2-carboxamide;

266) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinolin-1 β-carboxamide;

267) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -6-fluoro-4- methoxyquinoline-3-carboxamide;

268) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indole-2-carboxamide;

269) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- fluorobenzo [b] thiophene-2-carboxamide;

270) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- methylbenzo [b] thiophene-2-carboxamide;

271) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,3-dimethyl- 1H-pyrazolo [3,4-b] pyridin-5-carboxamide;

272) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyridine-6-carboxamide;

273) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1,5-a ] pyrimidine-2-carboxamide;

274) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylbenzo [b] thiophene-2-carboxamide;

275) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide;

276) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyridazine-4-carboxamide;

277) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide;

278) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-6-carboxamide;

279) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-8-carboxamide;

280) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylimidazo [1, 2-a] pyridine-2-carboxamide;

281) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methyl [1, 2,4] triazolo [1,5-a] pyrimidine-2-carboxamide;

282) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5,7-dimethylpyrazolo [ 1,5-a] pyrimidine-3-carboxamide;

283) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide;

284) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,6-diisopropyl- 1H-pyrazolo [3,4-b] pyridin-4-carboxamide;

285) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyrimidine-2-carboxamide;

286) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-oxo-1, 2-dihydroisoquinoline-3-carboxamide;

287) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylimidazo [1,5-a] pyridin-1-carboxamide;

288) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2H- indazole-3-carboxamide;

289) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [1, 5-a] pyrimidine-6-carboxamide;

290) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;

291) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-1H- benzo [d] imidazole-2-carboxamide;

292) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-5-carboxamide;

293) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indazole-3-carboxamide;

294) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-5- carboxamide;

295) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-3a, 7a-dihydro-1H-indazole-3-carboxamide;

296) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-4-carboxamide;

297) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-3- carboxamide;

298) tert-butyl (tert-butoxycarbonylamino) (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) methylene carbamate ;

299) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indazole-5- carboxamide;

300) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methyl-1H- pyrazole-5-carboxamide;

301) 1-amino-9b- (furan-2-carboxamido) -7-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-yl furan-2-carboxylate ;

302) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;

303) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;

304) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;

305) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;

306) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide; and

307) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrahydrofuran-2-carboxamide.

Preferred examples of the indanone derivative represented by chemical formula 1 are as follows:

compounds 29), 45) -47), 49) -63), 65) -67), 70) -75), 77) -78) and 87) -307).

More preferred examples of the indanone derivative represented by chemical formula 1 include:

Compounds 196) -207), 212) -217), 228), 231) -235), 237) -238) and 241) -307).

Derivatives of indanone represented by chemical formula 1 of the present invention can be used in the form of pharmaceutically acceptable salts. Suitable are acid addition salts formed with pharmaceutically acceptable free acids. As used herein, the term “pharmaceutically acceptable salt” refers to any organic or inorganic salt of the basic compounds of chemical formula 1 that does not exhibit side effects in which the beneficial activity of the basic compounds of chemical formula 1 degrades if the salt is present in a concentration that does not cause toxicity and harm to the body. Free acids may be inorganic or organic. Examples of suitable inorganic free acids include hydrochloric acid, bromic acid, nitric acid, sulfuric acid, perchloric acid, and phosphoric acid. As organic acids, citric acid, acetic acid, lactic acid, maleic acid, fumaric acid, gluconic acid, methanesulfonic acid, gluconic acid, succinic acid, tartaric acid, galacturonic acid, embonic acid, glutamic acid, aspartic acid, oxalic acid can be used. acid, (D) - or (L) malic acid, maleic acid, methanesulfonic acid, ethanesulfonic acid, 4-toluenesulfonic acid, salicylic acid, benzoic acid or malonic acid ota. Pharmaceutically acceptable salts may include alkali metal salts (sodium salt, potassium salt and the like) and alkaline earth metal salts (calcium salt, magnesium salt and the like). Acid addition salts that can be used in the present invention include, but are not limited to, acetate, aspartate, benzoate, besylate, bicarbonate / carbonate, bisulfate / sulfate, borate, camsylate, citrate, edisylate, esylate, formate, fumarate, gluceptate, gluconate , glucuronate, hexafluorophosphate, gibenzat, hydrochloride / chloride, hydrobromide / bromide, hydroiodide / iodide, isethionate, lactate, malate, maleate, malonate, mesylate, methyl sulphate, naphthylate, 2-napsylate, nicotinate, nitrate, pamorate, pamphorate, pamphate phosphate / hydrogen phosphate / dihydride ofphosphate, sugar, stearate, succinate, tartrate, tosylate, trifluoroacetate, aluminum, arginine, benzatin, calcium, choline, diethylamine, diolamine, glycine, lysine, magnesium, meglumine, amine, potassium, sodium and ta trifluoroacetate are preferred. Additive salts of the present invention can be obtained by conventional methods. For example, they can be prepared by dissolving a compound of chemical formula 1 in an organic solvent such as methanol, ethanol, acetone, methylene chloride or acetonitrile, and adding an excess of organic acids or an excess of aqueous solutions of inorganic acids, so that salts precipitate or crystallize. These addition salts can be prepared by precipitation or crystallization, or by evaporation of the solvent or excess acid and drying or suction filtration of the precipitated salt.

Also, pharmaceutically acceptable metal salts formed with bases may be in the range of pharmaceutically acceptable salts of the compounds of the present invention. Examples of metal salts useful in the present invention include alkali metal salts and alkaline earth metal salts. For example, the compound of the present invention may be dissolved in excess alkali metal hydroxide or alkaline earth metal hydroxide in water, and, after filtering the solution to remove undissolved salts of the compound, the filtrate may be dried to obtain pharmaceutically acceptable salts of the compound of the present invention. Suitable for use in pharmaceuticals are sodium, potassium or calcium salts. Appropriate silver salts can be prepared by reacting alkali metal salts or alkaline earth metal salts with a suitable silver salt (e.g., silver nitrate).

The scope of the present invention includes not only indanone derivatives of the compounds of chemical formula 1 and their pharmaceutically acceptable salts, but also solvates, hydrates and isomers obtained from them, if they have the same effect.

The present invention also relates to a method for producing the indanone derivative of the present invention. In one embodiment, the method comprises acylating or alkylating a compound of chemical formula 1 with a base in a solvent to obtain a compound of chemical formula 1a (step 1), as illustrated in the following reaction scheme 1:

[Reaction scheme 1]

,

,

Where

the compound of chemical formula 1a is a derivative of chemical formula 1, its pharmaceutically acceptable salt or its optical isomer,

A ¹ , A ² , A ³ , A ⁴ , D, E, G ¹ , G ² , G ³ , G ⁴ , X, Y and Z are as defined in chemical formula 1,

J and L, independently or optionally, are the same as A ¹ , A ² , A ³ , A ⁴ , D, E, G ¹ , G ² , G ³ or G ⁴ .

As a solvent suitable in reaction scheme 1, diisopropyl ether, diethyl ether, dioxane, tetrahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMA), dimethyl sulfoxide (DMSO), methylene chloride (MC), chlorobenzene, or toluene can be used benzene.

The base used in this reaction may be pyridine (PPT), 4-dimethylaminopyridine, trimethylamine or ethylamine.

In another embodiment, the method includes:

reacting a compound of chemical formula 1 with thionyl chloride or oxalyl chloride in the presence of a base in a solvent and then reacting with ammonia to obtain a compound of chemical formula 2 (step 1); and

acylating or alkylating a compound of chemical formula 2 in the presence of a base in a solvent to obtain a compound of chemical formula 1b (step 2), as illustrated in the following reaction scheme 2:

[Reaction scheme 2]

,

,

Where

the compound of chemical formula 1b is a derivative of chemical formula 1, its pharmaceutically acceptable salt or its optical isomer,

A ¹ , A ² , A ³ , A ⁴ , D, E, G ¹ , G ² , G ³ , G ⁴ , X, Y and Z are as defined in chemical formula 1,

J and L, independently or optionally, are the same as A ¹ , A ² , A ³ , A ⁴ , D, E, G ¹ , G ² , G ³ or G ⁴ .

The solvents used in stages 1 and 2 of reaction scheme 2 of this method can be independently selected from diisopropyl ether, diethyl ether, dioxane, tetrahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMA), dimethyl sulfoxide (DMSO) MC, methylene chloride (DMSO) ), chlorobenzene, toluene or benzene.

Pyridine (PPT), trimethylamine, ethylamine or triphosgene can be used as the base for the acylation or alkylation reaction in this method.

In accordance with one aspect of the present invention, there is also contemplated a pharmaceutical composition for the prophylaxis or treatment of a viral disease, comprising an indanone derivative represented by chemical formula 1, a pharmaceutically acceptable salt thereof or an optical isomer thereof as an active ingredient.

The viral disease targeted by the pharmaceutical composition of the present invention is a disease caused by picornaviruses, including coxsackie viruses, entero, polio and rhinoviruses. Examples of viral diseases include poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, pemphigus viral pemphigus, pemphigus, hepatitis A, myositis, myocarditis, pancreatitis, epidemic myalgia, encephalitis, influenza, vesicular pharyngitis and

With excellent antiviral activity against picornaviruses, such as Coxsackie, entero, echo, polio and rhinoviruses, as well as low cytotoxicity, the indanone derivative of chemical formula 1 can be used as an active ingredient in the pharmaceutical composition for the prevention or treatment of various viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus, hepatitis A, myositis, myocarditis, pancreas tit, diabetes epidemic myalgia, encephalitis, influenza, vesicular pharyngitis, foot and mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis and otitis media.

Clinically, the compound of the present invention can be administered in the form of various formulations. For this, the compound is typically formulated with a diluent or excipient, such as a filler, a thickener, a binding agent, a moisturizing agent, a disintegrant, a surfactant, and the like.

Solid preparations intended for oral administration of a compound of the present invention may be in the form of tablets, pills, powders, granules, capsules, troches, and the like. Such solid preparations are formulated in combination with at least one excipient such as starch, calcium carbonate, sucrose, lactose or gelatin. In addition to a simple excipient, a lubricant such as magnesium stearate, talc or the like can also be added. Liquid preparations intended for oral administration include suspensions, oral solutions, emulsion, syrups and the like. In addition to a simple diluent, such as water or paraffin oil, various excipients, such as wetting agents, sweeteners, flavorings, preservatives, and the like, may be contained in liquid preparations for oral administration of a compound of the present invention.

Also, the compound of the present invention may be in parenteral dosage form, such as sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilisates, suppositories and the like. For non-aqueous solvents and suspensions, propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and esters such as ethyl oleate may be suitable. Key suppository materials include vitepsol, macrogol, tween 61, cocoa butter, bay leaves and glycerogelatin.

The compound of the present invention is administered in a therapeutically effective amount. The effective dose of a compound of the present invention varies depending on various factors, including the age, weight, gender and health of the patient, route of administration and severity of the disease. Typically, the compound of the present invention can be administered in a daily dose of from 0.001 to 100 mg / kg and, preferably, in a daily dose of from 0.01 to 35 mg / kg. For an adult patient weighing 70 kg, the dose of the compound of the present invention may typically be in the range from 0.07 to 7000 mg / day, and preferably from 0.7 to 2500 mg / day. The compounds can be administered in a single dose or can be divided into several doses at a regular time interval in accordance with the instructions of the doctor or pharmacist who is responsible for monitoring or monitoring the administration of the drug.

Options for implementation

A better understanding of the present invention can be achieved using the following examples, which are illustrative and should not be construed as limiting the present invention.

<EXAMPLE 1> 4b, 9b-Dihydroxy-7-methyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (6.00 g, 33.6 mmol) and m-cresol (3.78 ml, 33.6 mmol) were dissolved in acetic acid (30 ml) and heated for 3 hours at the boil under reflux. After cooling, the precipitate thus formed was washed with acetic acid and water in the indicated order to obtain the title compound as a white solid. 7.55 g (83%).

Melting point: 145-147 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.26 (s, 3H, CH ₃ ) 6.63 (s, 1H, ArH) 6.75 (d, J = 7.8 Hz, 1H, ArH) 7.34 (d, J = 7.8 Hz, 1H, ArH) 7.54 (t, J = 7.5 Hz, 1H, ArH) 7.74-7.81 (m, 2H, ArH) 7, 97-8.00 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 268.

<EXAMPLE 2> 7-Methyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate

4b, 9b-Dihydroxy-7-methyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (1.00 g, 3.7 mmol) was completely dissolved in anhydrous dichloromethane (50 ml). Anhydrous acetic acid (0.7 ml, 7.4 mmol), pyridine (0.3 ml, 3.7 mmol) and 4-dimethylaminopyridine (0.1 g) were added to this solution, and stirred at room temperature for 3 hours. . Then the reaction mixture was extracted with dichloromethane, the organic layer was concentrated and purified by column chromatography (ethyl acetate: hexane = 1: 8) to obtain the title compound. 0.04 g (3%).

Melting point: 167-169 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.15 (s, 3H, OAc) 2.16 (s, 3H, OAc) 2.30 (s, 3H, CH ₃ ) 6.69 (s, 1H , ArH) 6.88 (d, J = 7.8 Hz, 1H, ArH) 7.47 (d, J = 7.7 Hz, 1H, ArH) 7.58 (t, J = 7.4 Hz, 1H, ArH) 7.75-7.84 (m, 2H, ArH) 8.14 (d, J = 7.7 Hz, 1H, ArH). MS (EI): 352.

<EXAMPLE 3> Ethyl 2- (4b, 9b-dihydroxy-6-methoxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-8-yl) acetate

Ninhydrin (2.54 g, 14.2 mmol) and ethyl 2- (4-hydroxy-3-methoxyphenyl) acetate (3.00 g, 14.2 mmol) were dissolved in acetic acid (15 ml) and heated for 21 hours at reflux, followed by extraction with ethyl acetate. The concentrate was purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. 1.46 g (29%).

Melting point: 133-136 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (t, J = 7.2 Hz, 3H, CH ₃ ) 3.56 (s, 2H, CH ₂ ) 3.82 (s, 3H OCH ₃ ) 4.11-4.18 (q, J = 7.2 Hz, 14.4H, 2H, OCH ₂ ) 6.89 (s, 1H, ArH) 7.12 (s, 1H, ArH) 7, 56-8.14 (m, 4H, ArH). MS (EI): 370.

<EXAMPLE 4> 4b, 9b-Dihydroxy-7,8-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (4.37 g, 24.5 mmol) and 3,4-dimethylphenol (3.00 g, 24.5 mmol) were dissolved in acetic acid (15 ml) and heated for 23 hours under reflux. After cooling, the precipitate thus formed was washed with acetic acid and water in the indicated order to obtain the title compound as a white solid. 5.43 g (78%).

Melting point: 198-200 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.15 (m, 6H, CH ₃ ) 6.55 (s, 1H, ArH) 7.22 (s, 1H, ArH) 7.70-7.88 (m, 4H, ArH). MS (EI): 282.

<EXAMPLE 5> 4b, 9b-Dihydroxy-4b, 9b-dihydro-10H-indeno [1,2-b] benzofuran-10-one

Ninhydrin (1.00 g, 5.6 mmol) and phenol (0.53 g, 5.6 mmol) were dissolved in acetic acid (20 ml) and heated for 23 hours at the boil under reflux. The reaction mixture was cooled, washed with acetic acid and water, and then recrystallized from dichloromethane to give the title compound as a white solid. 0.37 g (26%).

Melting point: 155-159 ° C.

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 5.87 (s, 1H, OH) 6.72 (s, 1H, OH) 6.78 (d, J = 8.4 Hz, 1H, ArH ) 6.95 (t, J = 6.6 Hz, 1H, ArH) 7.27 (t, J = 6.9 Hz, 1H, ArH) 7.48 (d, J = 7.3 Hz, 1H, ArH) 7.64 (t, J = 7.5 Hz, 1H, ArH) 7.75 (d, J = 7.8 Hz, 1H, ArH) 7.91 (t, J = 13.4 Hz, 1H , ArH) 8.01 (d, J = 4.8 Hz, 1H, ArH). MS (EI): 254.

<EXAMPLE 6> 8-fluoro-4b, 9b-dihydroxy-4b, 9b-dihydro-10H-indeno [1,2-b] benzofuran-10-one

Ninhydrin (1.00 g, 5.6 mmol) and 4-fluorophenol (0.63 g, 5.6 mmol) were dissolved in acetic acid (20 ml) and heated for 23 hours under reflux. After cooling, the precipitate thus formed was washed with acetic acid and water and recrystallized from dichloromethane to give a white solid. The precipitate was purified by column chromatography (ethyl acetate: hexane = 1: 4) and washed with dichloromethane to give the title compound. 0.57 g (37%).

Melting point: 189-193 ° C.

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 5.98 (s, 1H, OH) 6.81 (q, J = 9.0 Hz, 4.0 Hz, 1H, ArH) 6.88 (s, 1H, OH) 7.06 (dt, J = 9.0, 2.7 Hz, 1H, ArH) 7.20 (dd, J = 7.8 Hz, 3.0 Hz, 1H, ArH) 7.66 (t, J = 6.9 Hz, 1H, ArH) 7.77 (d, J = 7.8 Hz, 1H, ArH) 7.92 (t, J = 7.8 Hz, 1H, ArH ) 8.00-8.03 (m, 1H, ArH). MS (EI): 272.

<EXAMPLE 7> 4b, 9b-Dihydroxy-7-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

3-Methoxyphenol (2.09 g, 16.8 mmol) and ninhydrin (3.00 g, 16.8 mmol) were dissolved in acetic acid (20 ml) and heated for 2 hours under reflux. The reaction mixture was then extracted with ethyl acetate, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4), followed by recrystallization from ethyl acetate and hexane to give the title compound. 1.25 g (26%).

Melting point: 98-100 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 3.82 (s, 3H, OCH ₃ ) 6.39 (s, 1H, ArH) 6.52 (d, 1H, J = 9.0 Hz, ArH) 7.37 (d, 1H, J = 9.0 Hz, ArH) 7.57 (t, 1H, J = 9.0 Hz, ArH) 7.78-7.81 (m, 2H, ArH) 7, 99 (d, J = 9.0 Hz, 1H, ArH). MS (EI): 284.

<EXAMPLE 8> 6,7-Dichloro-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and 2,3-chlorophenol (2.16 g, 16.8 mmol) were dissolved in acetic acid (20 ml) and heated for 28 hours at the boil under reflux. The precipitate thus formed was washed with dichloromethane to give the title compound as a white solid. 2.35 g (43%).

Melting point: 142-150 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 7.06 (d, J = 8.1 Hz, 1H, ArH) 7.33 (d, J = 8.1 Hz, 1H, ArH) 7.61 ( t, J = 7.5 Hz, 1H, ArH) 7.80-7.88 (m, 2H, ArH) 8.07 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 323.

<EXAMPLE 9> 7-Ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and m-ethyl phenol (2.05 g, 16.8 mmol) were dissolved in acetic acid (20 ml) and heated for 4 hours at the boil under reflux. After cooling, the precipitate thus formed was washed with dichloromethane to give the title compound as a white solid. 2.80 g (59%).

Melting point: 168-169 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (t, J = 7.8 Hz, 3H, CH ₃ ) 2.53-2.60 (q, J = 15.3 Hz, 7, 5 Hz, CH ₂ ) 3.93 (s, 1H, OH) 4.75 (s, 1H, OH) 6.68 (s, 1H, ArH) 6.80 (d, J = 6.0 Hz, 1H , ArH) 7.38 (d, J = 7.8 Hz, 1H, ArH) 7.55 (t, J = 7.5 Hz, 1H, ArH) 7.79 (t, J = 9.0 Hz, 2H, ArH) 8.00 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 282.

<EXAMPLE 10> 4b, 9b-Dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and m-isopropylphenol (2.29 g, 16.8 mmol) were dissolved in acetic acid (20 ml) and heated for 2 hours under reflux. After cooling, the precipitate thus formed was washed with dichloromethane to give the title compound as a white solid. 2.82 g (56%).

Melting point: 195-198 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 8.1 Hz, 6H, CH ₃ ) 2.77-2.86 (m, 1H, CH) 4.14 (s, 1H, OH) 4.85 (s, 1H, OH) 6.70 (s, 1H, ArH) 6.82 (d, J = 7.8 Hz, 1H, ArH) 7.40 (d, J = 7 8 Hz, 1H, ArH) 7.54 (t, J = 7.8 Hz, 1H, ArH) 7.75-7.82 (m, 2H, ArH) 8.00 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 296.

<EXAMPLE 11> 7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate

4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (2.00 g, 6.7 mmol) was completely dissolved in anhydrous tetrahydrofuran (20 ml) and mixed with anhydrous acetic acid (1.38 g, 13.5 mmol), pyridine (0.53 g, 6.7 mmol), 4-dimethylaminopyridine (0.2 g) at room temperature for 12 hours at stirring. The reaction mixture was concentrated and extracted repeatedly with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.27 g (11%).

Melting point: 138-140 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.14 (s, 3H, OAc) 2.16 (s, 3H, OAc) 2.83-2.87 (m, 1H, CH) 6.75 (s, 1H, ArH) 6.94 (d, J = 7.8 Hz, 1H, ArH) 7.51 (d, J = 7 5 Hz, 1H, ArH) 7.59 (t, J = 7.5 Hz, 1H, ArH) 7.75-7.85 (m, 2H, ArH) 8.16 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 380.

<EXAMPLE 12> 4b, 9b-Dihydroxy-8-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and p-methoxyphenol (2.09 g, 16.8 mmol) were dissolved in acetic acid (20 ml) and heated for 6 hours at the boil under reflux. After cooling, the precipitate thus formed was washed with acetic acid and water in the indicated order to obtain the title compound as a yellow solid. 4.00 g (83%).

Melting point: 186-189 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 3.72 (s, 3H, OCH ₃ ) 6.59 (d, J = 8.8 Hz, 1H, ArH) 6.70 (dd, J = 8, 8 Hz, 1H, ArH) 6.97 (d, J = 2.8 Hz, 1H, ArH) 7.43 (t, J = 7.9 Hz, 1H, ArH) 7.64-7.71 (m , 2H, ArH) 7.84-7.87 (d, J = 7.7 Hz, 1H, ArH). MS (EI): 284.

<EXAMPLE 13> 4b, 9b-Dihydroxy-6-phenyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and m-phenylphenol (2.86 g, 16.8 mmol) were added to acetic acid (20 ml) and heated for 20 hours under reflux. After removing the solvent by concentration in vacuo, the concentrate was repeatedly extracted with dichloromethane. The concentrated organic layer was crystallized with dichloromethane and hexane to give the title compound as a white solid. 4.10 g (73%).

Melting point: 182-183 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 7.03 (t, J = 6.0 Hz, 1H, ArH) 7.30-7.41 (m, 1H, ArH) 7.42-7.48 (m, 4H, ArH) 7.54 (t, J = 7.8 Hz, 1H, ArH) 7.63 (d, J = 8.4 Hz, 2H, ArH) 7.76-7.81 (m , 2H, ArH) 8.01 (d, J = 8.1 Hz, 1H, ArH). MS (EI): 330.

<EXAMPLE 14> 4b, 9b-Dihydroxy-8-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (3.00 g, 16.8 mmol) and 4-nitrophenol (2.34 g, 16.8 mmol) were added to acetic acid (20 ml) and heated for 5 hours at the boil under reflux. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 3) to obtain the title compound. White matter. 0.80 g (16%).

Melting point: 206-207 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 6.94 (d, J = 9.0 Hz, 1H, ArH) 7.63 (t, J = 7.8 Hz, 1H, ArH) 7.80- 7.90 (m, 2H, ArH) 8.03 (d, J = 7.8 Hz, 1H, ArH) 8.24 (d, J = 9.0 Hz, 1H, ArH) 8.42 (d, J = 2.4 Hz, 1H, ArH). MS (EI): 299.

<EXAMPLE 15> 4b, 11b-Dihydroxy-4bH-indeno [1,2-b] naphtho [2,3-d] furan-12 (11bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 2-naphthol (0.81 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 6 hours under reflux. After cooling, the precipitate thus formed was washed with acetic acid and water in the indicated order to obtain the title compound as a white solid. 1.31 g (77%).

Melting point: 220-221 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 7.06 (d, J = 8.7 Hz, 1H, ArH) 7.37 (t, J = 7.5 Hz, 1H, ArH) 7.52- 7.62 (m, 2H, ArH) 7.76-7.83 (m, 4H, ArH) 8.04 (d, J = 7.8 Hz, 1H, ArH) 8.38 (d, J = 8 4 Hz, 1H, ArH). MS (EI): 304.

<EXAMPLE 16> 6b, 11b-Dihydroxy-6bH-indeno [1,2-b] naphtho [2,1-d] furan-7 (11bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 1-naphthol (0.81 g, 5.61 mmol) were added to acetic acid (20 ml) and heated for 7 hours under reflux. After cooling the reaction mixture, the precipitate thus formed was washed with acetic acid and water in this order to obtain the title compound as a white solid. 0.96 g (56%).

Melting point: 216-218 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 7.43-7.57 (m, 5H, ArH) 7.75-7.83 (m, 3H, ArH) 8.03-8.12 (m, 2H, ArH). MS (EI): 304.

<EXAMPLE 17> 4b, 9b-Dihydroxy-8-propyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and p-propylphenol (0.76 g, 5.61 mmol) were added to acetic acid (20 ml) and heated for 16 hours under reflux. The reaction mixture was extracted repeatedly with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 3 to 1: 1) to obtain the title compound. 1.10 g (66%).

Melting point: 126-127 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.83-0.90 (t, J = 7.4 Hz, 3H, CH ₃ ) 1.46-1.57 (m, 2H, CH ₂ ) 2 45 (t, J = 7.8 Hz, 2H, CH ₂ ) 6.74 (d, J = 8.4 Hz, 1H, ArH) 7.08 (dd, J = 1.8, 8.4 Hz , 1H, ArH) 7.31 (s, 1H, ArH) 7.55 (t, J = 7.8 Hz, 1H, ArH) 7.77-7.82 (m, 2H, ArH) 8.00 ( d, J = 7.5 Hz, 1H, ArH). MS (EI): 296.

<EXAMPLE 18> 8-Ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and p-ethylphenol (0.68 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 15 hours at the boil under reflux. After cooling the reaction mixture for 12 hours, the precipitate thus formed was washed with acetic acid and water in this order to obtain the title compound as a yellowish-white solid. 1.10 g (69%).

Melting point: 157-159 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (t, J = 7.4 Hz, 3H, CH ₃ ) 2.50-2.61 (q, J = 7.6 Hz, 2H, CH ₂ ) 3H, OAc) 6.74 (d, J = 8.4 Hz, 1H, ArH) 7.10 (d, J = 8.4 Hz, 1H, ArH) 7.33 (s, 1H, ArH ) 7.54 (t, J = 8.0 Hz, 1H, ArH) 7.76-7.83 (m, 2H, ArH) 8.00 (d, J = 7.6 Hz, 1H, ArH). MS (EI): 282.

<EXAMPLE 19> 8-sec-Butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and p-sec-butylphenol (0.84 g, 5.61 mmol) were added to acetic acid (20 ml) and heated for 20 hours under reflux. The reaction mixture was extracted repeatedly with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.80 g (46%).

Melting point: 134-136 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.77 (t, J = 7.2 Hz, 3H, CH ₃ ) 1.16 (d, J = 6.9 Hz, 3H, CH ₃ ) 1, 31-1.43 (m, 2H, CH ₂ ) 2.49-2.56 (m, 1H, CH) 6.75 (d, J = 8.1 Hz, 1H, ArH) 7.09 (d, J = 8.4 Hz, 1H, ArH) 7.33 (s, 1H, ArH) 7.59 (m, 1H, ArH) 7.79-7.83 (m, 2H, ArH) 8.00 (d , J = 7.5 Hz, 1H, ArH). MS (EI): 310.

<EXAMPLE 20> 8-tert-Butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and p-tert-butylphenol (0.84 g, 5.61 mmol) were added to acetic acid (20 ml) and heated for 16 hours under reflux. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.60 g (34%).

Melting point: 187-188 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.22 (s, 9H, CH ₃ ) 6.78 (d, J = 8.4 Hz, 1H, ArH) 7.27-7.28 (m, 1H, ArH) 7.46 (d, J = 2.1 Hz, 1H, ArH) 7.57 (t, J = 7.5 Hz, 1H, ArH) 7.79-7.84 (t, J = 7.5 Hz, 2H, ArH) 8.00 (d, J = 2.1 Hz, 1H, ArH). MS (EI): 310.

<EXAMPLE 21> 6-tert-Butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (0.60 g, 5.6 mmol) and 2-tert-butylphenol (0.84 g, 5.6 mmol) were dissolved in acetic acid (10 ml) and heated for 7 hours under reflux. After cooling the reaction mixture, the precipitate thus formed was washed with acetic acid and water in this order to obtain the title compound as a white solid. 1.09 g (62%).

Melting point: 148-152 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.35 (s, 9H, CH ₃ ) 6.93 (t, J = 7.8 Hz, 1H, ArH) 7.23-7.37 (m, 2H, ArH) 7.57 (t, J = 7.4 Hz, 1H, ArH) 7.80 (t, J = 7.8 Hz, 2H, ArH) 8.05 (d, J = 7.8 Hz , 1H, ArH). MS (EI): 310.

<EXAMPLE 22> 4b, 9b-Dihydroxy-7,8,9-trimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 3,4,5-trimethylphenol (0.76 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 16 hours under reflux . The reaction mixture was extracted repeatedly with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 1.01 g (60%).

Melting point: 212-214 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.05 (s, 3H, CH ₃ ) 2.19 (s, 3H, CH ₃ ) 2.44 (s, 3H, CH ₃ ) 6.53 (s , 1H, ArH) 7.53 (t, J = 6.9 Hz, 1H, ArH) 7.74-7.80 (m, 2H, ArH) 7.96 (d, J = 7.2 Hz, 1H , ArH). MS (EI): 296.

<EXAMPLE 23> 4b, 9b-Dihydroxy-8-tert-pentyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 4-tert-pentylphenol (0.92 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 32 hours under reflux. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 1.28 g (70%).

Melting point: 175-176 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.63 (t, J = 7.5 Hz, 3H, CH ₃ ) 1.22 (s, 6H, CH ₃ ) 1.53-1.60 (q ., J = 15.0, 7.5 Hz, 2H, CH ₂ ) 6.78 (d, J = 8.4 Hz, 1H, ArH) 7.28 (m, 1H, ArH 7.46 (d, J = 2.1 Hz, 1H, ArH) 7.57 (t, J = 7.5 Hz, 1H, ArH) 7.79-7.84 (t, J = 7.5 Hz, 2H, ArH) 8 00 (d, J = 6.90 Hz, 1H, ArH). MS (EI): 324.

<EXAMPLE 24> 6,8-di-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 2,4-tert-butylphenol (1.16 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 16 hours under reflux . The reaction mixture was repeatedly extracted with dichloromethane and the organic layer was dried, filtered and concentrated in vacuo. The solid thus formed was washed with hexane to give the title compound. 0.60 g (34%).

Melting point: 200-203 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.25 (s, 9H, CH ₃ ) 1.33 (s, 9H, CH ₃ ) 7.31 (d, J = 2.1 Hz, 1H, ArH ) 7.35 (d, J = 2.1 Hz, 1H, ArH) 7.55 (t, J = 9.0 Hz, 1H, ArH) 7.76-7.81 (m, 2H, ArH) 8 01 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 366.

<EXAMPLE 25> 6,8-di-tert-butyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate

6,8-di-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.60 g, 0.60 mmol) completely dissolved in anhydrous tetrahydrofuran (20 ml) and reacted overnight with anhydrous acetic acid (0.33 g, 3.28 mmol), pyridine (0.13 g, 1.64 mmol) and 4-dimethylaminopyridine (0.06 g) at room temperature with stirring. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 3) to obtain the title compound. 0.61 g (61%).

Melting point: 242-247 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.29 (s, 18H, CH ₃ ) 2.13 (s, 3H, OAc) 2.18 (s, 3H, OAc) 7.31 (d, J = 2.1 Hz, 1H, ArH) 7.43 (d, J = 1.8 Hz, 1H, ArH) 7.57 (t, J = 7.5 Hz, 1H, ArH) 7.73-7, 84 (m, 2H, ArH) 8.19 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 450.

<EXAMPLE 26> 4b, 9b-Dihydroxy-8-nonyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and nonylphenol (1.23 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 20 hours at the boil under reflux. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 1.01 g (47%).

Melting point: 108-110 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.50-1.28 (m, 16H, CH ₂ ) 2.09 (s, 3H, CH ₃ ) 6.76 (d, J = 8.4 Hz , 1H, ArH) 7.38-7.44 (m, 1H, ArH) 7.56 (t, J = 7.8 Hz, 1H, ArH) 7.81 (t, J = 7.5 Hz, 2H , ArH) 8.01 (t, J = 7.5 Hz, 1H, ArH). MS (EI): 380.

<EXAMPLE 27> 4b, 9b-Dihydroxy-8-pentadecyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Ninhydrin (1.00 g, 5.61 mmol) and 2-pentadecylphenol (1.70 g, 5.61 mmol) were dissolved in acetic acid (20 ml) and heated for 20 hours under reflux. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 1.01 g (37%).

Melting point: 105-110 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.87 (t, J = 6.3 Hz, 3H, CH ₃ ) 1.24 (s, 24H, CH ₂ ) 1.52-1.54 (m , 2H, CH ₂ ), 2.53 (t, J = 7.6 Hz, 2H, CH ₂ ) 6.68 (s, 1H, ArH) 6.81 (d, J = 7.6 Hz, 1H, ArH) 7.40 (d, J = 7.8 Hz, 1H, ArH) 7.58 (t, J = 7.0 Hz, 1H, ArH) 7.83 (t, J = 6.80 Hz, 2H , ArH) 8.02 (d, J = 8.4 Hz, 1H, ArH). MS (EI): 464.

<EXAMPLE 28> 6,8-Bis- (1,1-dimethylpropyl) -4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

Ninhydrin (1.00 g, 5.6 mmol) and 2,4-di-tert-pentylphenol (1.31 g, 5.6 mmol) were added to acetic acid (20 ml) and heated for 16 hours while boiling with reflux condenser. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 1.28 g (58%).

Melting point: 195-222 ° C.

¹ H-NMR (300 MHz, CD ₃ OD) δ 0.44 (t, J = 7.5 Hz, 3H, CH ₃ ) 0.62 (t, J = 7.5 Hz, 3H, CH ₃ ) 1 23 (s, 9H, CH ₃ ) 1.56 (s, 3H, CH ₃ ) 1.58-1.63 (q, J = 15.0 Hz, 7.5 Hz, 2H, CH ₂ ) 1 , 77-1.85 (m, 2H, CH ₂ ) 7.11 (s, 1H, ArH) 7.31 (s, 1H, ArH) 7.57 (t, J = 7.8 Hz, 1H, ArH ) 7.74 (d, J = 7.8 Hz, 1H, ArH) 7.81 (t, J = 8.4 Hz, 1H, ArH) 7.96 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 394.

<EXAMPLE 29> Isopropyl 4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate

To a solution of 4b, 9b-dihydroxy-1-isocyanato-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (70 mg, 0.2 mmol) in anhydrous tetrahydrofuran 2M ammonia (0.21 ml in isopropyl alcohol) was added dropwise. The reaction mixture was heated for 4 hours at the boil under reflux and concentrated in vacuo, followed by purification using column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 30 mg (38%).

Melting point: 200-202 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 6.9, 1.8 Hz, 6H, CH ₃ ) 1.27-1.34 (m, 6H, CH ₃ ) 2 78-2.87 (m, 1H, CH) 3.95 (s, 1H, OH) 4.77 (s, 1H, OH) 4.96-5.05 (m, 1H, CH) 6.71 (s, 1H, ArH) 6.84 (d, J = 8.1 Hz, 1H, ArH) 7.42 (d, J = 8.1 Hz, 1H, ArH) 7.53 (d, J = 7 , 2 Hz, 1H, ArH) 7.72 (t, J = 8.1 Hz, 1H, ArH) 8.27 (d, J = 8.4 Hz, 1H, ArH) 9.29 (s, 1H, NH). MS (EI): 397.

<EXAMPLE 30> 5a, 10a-dihydroxy-2,3,5a, 10a-tetrahydro-diindeno [1,2-b: 5 ′, 6′-d] furan-10 (1H) -one

To a solution of ninhydrin (1.00 g, 5.61 mmol) in acetic acid (20 ml) was added 1- (3-hydroxyphenyl) ethanone (0.75 g, 5.61 mmol), followed by heating for 3 hours at 110 ° C. The reaction mixture was repeatedly extracted with dichloromethane, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. White matter. 1.56 g (94%).

Melting point: 214-217 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.90-2.08 (m, 2H, CH ₂ ) 2.69-2.82 (m, 4H, CH ₂ ) 6.68 (s, 1H, ArH) 7.28 (d, J = 12.0 Hz, 1H, ArH) 7.54 (t, J = 7.2 Hz, 1H, ArH) 7.75-7.81 (m, 2H, ArH) 7.99 (d, J = 7.5 Hz, 1H, ArH). MS (EI): 294.

<EXAMPLE 31> 6b, 11b-Dihydroxy-1,2,3,4,6b, 11b-hexahydro-12-oxabenzo [4,5] pentaleno [2,1-a] naphthalene-7-one

To a solution of ninhydrin (1.00 g, 5.61 mmol) in acetic acid (20 ml) was added 5,6,7,8-tetrahydronaphthalen-1-ol (0.83 g, 5.61 mmol), followed by heating in for 3 hours at 110 ° C. After cooling, the precipitate thus formed was filtered to obtain the title compound as a white solid. 1.48 g (83%).

Melting point: 252-254 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.72-1.81 (m, 4H, CH ₂ ) 2.58-2.67 (m, 4H, CH ₂ ) 6.71 (d, J = 7.8 Hz, 1H, ArH) 7.21 (d, J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 8.4 Hz, 1H, ArH) 7.58-7.83 (m, 2H, ArH) 8.02 (d, J = 7.5 Hz, 1H, ArH). MS (EI): 308.

<EXAMPLE 32> 4b, 9b-Dihydroxy-7-isopropyl-2-methoxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one.

Isopropylphenol (0.065 g, 0.48 mmol) was added to a solution of 5-methoxynhydrin (0.10 g, 0.48 mmol) in acetic acid (20 ml) and heated for 15 hours at 110 ° C. The reaction mixture was repeatedly extracted with ethyl acetate, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. White matter. 0.12 g (77%).

Melting point: 98-102 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.24 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.78-2.85 (s, 1H, CH) 3.98 (s, 3H, OCH ₃ ) 6.71 (s, 1H, ArH) 6.82 (d, J = 7.8 Hz, 1H, ArH) 7.04-7.08 (dd, J = 8.4 Hz, 3 6 Hz, 1H, ArH) 7.39-7.42 (m, 2H, ArH) 7.70 (d, J = 8.4 Hz, 1H, ArH). MS (EI): 326.

<EXAMPLE 33> 7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis (2,2-dimethylpropanoate)

To a solution of 4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (1.00 g, 3.3 mmol) in anhydrous tetrahydrofuran, 2 , 2-dimethyl-propionichloride (0.81 g, 6.7 mmol), trimethylamine (0.40 g, 4.0 mmol) and 4-dimethylaminopyridine (0.1 g), followed by heating for 24 hours while boiling with reflux condenser. The reaction mixture was concentrated in vacuo and washed several times with dichloromethane. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 6) to obtain the title compound. 0.10 g (6%).

Melting point: 153-157 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16-1.26 (m, 24H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 6.73 (s, 1H, ArH ) 6.93 (d, J = 7.8 Hz, 1H, ArH) 7.48 (d, J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 7.5 Hz, 1H, ArH) 7.75-7.81 (m, 2H, ArH) 8.09 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 464.

<EXAMPLE 34> (2E, 2′E) -7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis ( 3-phenylacrylate)

To a solution of 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.3 mmol) in anhydrous tetrahydrofuran was added 3- phenylacryloyl chloride (1.12 g, 6.7 mmol), trimethylamine (0.40 g, 4.0 mmol) and 4-dimethylaminopyridine (0.1 g), followed by heating for 2 days at the boil under reflux. The reaction mixture was concentrated in vacuo and washed several times with ethyl acetate. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 8 to 1: 4) to obtain the title compound. 0.08 g (9%).

Melting point: 111-113 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (dd, J = 2.7 Hz, 6.8 Hz, 6H, CH ₃ ) 2.88-2.92 (m, 1H, CH) 6 37 (d, J = 16.0 Hz, 1H, CH) 6.52 (d, J = 16.0 Hz, 1H, CH) 6.81 (s, 1H, ArH) 6.99 (d, J = 7.3 Hz, 1H, ArH) 7.17-7.44 (m, 10H, ArH) 7.59-7.91 (m, 6H, CH, ArH) 8.25 (d, J = 7, 8 Hz, 1H, ArH). MS (EI): 556.

<EXAMPLE 35> 9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylacrylate

To a solution of 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.37 mmol) in anhydrous tetrahydrofuran was added acryloyl chloride ( 0.61 g, 6.74 mmol), trimethylamine (0.41 g, 4.0 mmol) and 4-dimethylaminopyridine (0.1 g), followed by heating for 24 hours at the boil under reflux. The reaction mixture was concentrated in vacuo and washed repeatedly with ethyl acetate. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 2 to 1: 1) to obtain the title compound. 0.02 g (1.7%).

Melting point: 95-97 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (d, J = 2.1 Hz, 7.2 Hz, 6H, CH ₃ ) 2.81-2.87 (m, 1H, CH) 3 91 (s, 1H, OH) 5.95 (d, J = 7.5 Hz, 2H, CH ₂ ) 6.19-6.28 (m, 1H, OH) 6.50 (d, J = 12 , 0 Hz, 1H, ArH) 6.73 (s, 1H, ArH) 6.88 (d, J = 8.1 Hz, 1H, ArH) 7.52 (d, J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 7.8 Hz, 1H, ArH) 7.80-7.91 (m, 2H, ArH). MS (EI): 350.

<EXAMPLE 36> 9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl-furan-2-carboxylatefuran-2- carboxylic acid

Furan-2-carbonyl chloride (0.88 g, 6.74 mmol), trimethylamine (0.34 g, 3.37 mmol), 4-dimethylaminopyridine (0.1 g) were added to solution 4b, 9b-dihydroxy-7- isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] indene-10-one (1.00 g, 3.37 mmol) in anhydrous tetrahydrofuran and heated for 24 hours under reflux. The reaction mixture was concentrated in vacuo and washed repeatedly with ethyl acetate. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.07 g (5%).

Melting point: 116-120 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 2.1 Hz, 6.9 Hz, 6H, CH ₃ ) 2.78-2.88 (m, 1H, CH) 4 77 (s, 1H, OH) 6.46-6.48 (s, 1H, CH) 6.71 (s, 1H, ArH) 6.90 (d, J = 7.2 Hz, 1H, ArH) 7.24 (s, 1H, ArH) 7.50-7.56 (m, 3H, CH, ArH) 7.73-7.82 (m, 2H, ArH) 7.93 (d, J = 7, 8 Hz, 1H, ArH). MS (EI): 390.

<EXAMPLE 37> Diethyl-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl dicarbonate

Ethoxycarbonyl chloride (0.81 g, 6.74 mmol), trimethylamine (0.34 g, 3.37 mmol) and 4-dimethylaminopyridine (0.1 g) were added to solution 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.37 mmol) in anhydrous tetrahydrofuran and heated for 24 hours under reflux. The reaction mixture was concentrated in vacuo and washed repeatedly with ethyl acetate, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.03 g (2%).

Melting point: 150-153 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 6.8, 2.8 Hz, 6H, CH ₃ ) 1.20-1.28 (m, 6H, CH ₃ ) 2 78-2.85 (m, 1H, CH) 4.14-4.30 (m, 4H, OCH ₂ ) 6.77 (s, 1H, ArH) 6.94 (d, J = 7.9 Hz , 1H, ArH) 7.53-7.62 (m, 2H, ArH) 7.76-7.87 (m, 2H, ArH) 8.18 (d, J = 7.8 Hz, 1H, ArH) . MS (EI): 440.

<EXAMPLE 38> Ethyl-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate

Ethoxycarbonyl chloride (0.81 g, 6.74 mmol), trimethylamine (0.34 g, 3.37 mmol) and 4-dimethylaminopyridine (0.1 g) were added to solution 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.37 mmol) in anhydrous tetrahydrofuran and heated for 24 hours under reflux. The reaction mixture was concentrated in vacuo and washed repeatedly with ethyl acetate, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.07 g (5%).

Melting point: 144-147 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 1.25 (t, J = 7.1 Hz, 3H, CH ₃ ) 2, 78-2.85 (m, 1H, CH) 4.12-4.19 (q, J = 14.3, 7.1 Hz, 2H, OCH ₂ ) 4.60 (s, 1H, OH) 6 69 (s, 1H, ArH) 6.88 (d, J = 7.8 Hz, 1H, ArH) 7.47-7.58 (m, 2H, ArH) 7.75-7.83 (m, 2H, ArH) 7.97 (d, J = 7.6 Hz, 1H, ArH). MS (EI): 368.

<EXAMPLE 39> Methyl 4b, 9b-dihydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-8-carboxylate

Methyl 3-hydroxybenzoate (0.42 g, 2.8 mmol) was added to a solution of ninhydrin (0.50 g, 2.8 mmol) in glacial acetic acid (10 ml) and heated for 27 hours under reflux . The reaction mixture was diluted in ethyl acetate, washed repeatedly with water, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.14 g (16%).

Melting point: 220-223 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 3.87 (s, 3H, OCH ₃ ) 4.05 (s, 1H, OH) 4.79 (s, 1H, OH) 6.87 (d, J = 8.4 Hz, 1H, ArH) 7.59 (t, J = 7.8 Hz, 1H, ArH) 7.80-7.86 (m, 2H, ArH) 7.98-8.02 (m , 2H, ArH) 8.20 (s, 1H, ArH). MS (EI): 312.

<EXAMPLE 40> 9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yldiethylcarbamate

Triethylamine (0.4 g, 4.0 mmol), diethylcarbamoyl chloride (0.91 g, 6.7 mmol) and 4-dimethylaminopyridine (0.1 g) were added to solution 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.3 mmol) in anhydrous tetrahydrofuran and heated under reflux. The reaction mixture was concentrated in vacuo, diluted in dichloromethane and washed many times with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.63 g (47%).

Melting point: 127-130 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.08-1.29 (m, 12H, CH ₃ ) 2.81-2.86 (m, 1H, CH) 3.22-3.45 (m , 4H, NCH ₂ ) 4.73 (s, 1H, OH) 6.70 (s, 1H, ArH) 6.91 (d, J = 7.9 Hz, 1H, ArH) 7.53-7.61 (m, 2H, ArH) 7.78-7.91 (m, 3H, ArH). MS (EI): 395.

<EXAMPLE 41> 4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yldiethylcarbamate

Triethylamine (0.4 g, 4.0 mmol), diethylcarbamoyl chloride (0.91 g, 6.7 mmol) and 4-dimethylaminopyridine (0.1 g) were added to solution 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.3 mmol) in anhydrous tetrahydrofuran and heated under reflux. The reaction mixture was concentrated in vacuo, diluted in dichloromethane and washed many times with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.02 g (1.5%).

Melting point: 101-104 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.06-1.30 (m, 12H, CH ₃ ) 2.79-2.88 (m, 1H, CH) 3.21-3.28 (m , 2H, NCH ₂ ) 3.36-3.47 (m, 2H, NCH ₂ ) 5.60 (s, 1H, OH) 6.73 (s, 1H, ArH) 6.85 (d, J = 7 , 2 Hz, 1H, ArH) 7.39 (d, J = 7.8 Hz, 1H, ArH) 7.54 (t, J = 6.3 Hz, 1H, ArH) 7.78-7.88 ( m, 2H, ArH) 8.00 (d, J = 7.5 Hz, 1H, ArH). MS (EI): 395.

<EXAMPLE 42> 2,3-Difluoro-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

m-Isopropylphenol (0.21 g, 1.5 mmol) was added to a solution of 5,6-difluoro-2,2-dihydroxy-1H-indene-1,3 (2H) -dione (0.33 g, 1.54 mmol) in glacial acetic acid (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was diluted in ethyl acetate and washed many times with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.32 g (63%).

Melting point: 134-136 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (d, J = 5.1 Hz, 6H, CH ₃ ) 1.19 (s, 3H, CH ₃ ) 2.79-2.88 (m , 1H, CH) 3.71 (s, 1H, OH) 4.65 (s, 1H, OH) 6.72 (s, 1H, ArH) 6.87 (d, J = 7.8 Hz, 1H, ArH) 7.37 (d, J = 8.1 Hz, 1H, ArH) 7.56 (t, J = 8.1 Hz, 1H, ArH) 7.77 (t, J = 6.7 Hz, 1H , ArH). MS (EI): 332.

<EXAMPLE 43> 1,4b, 9b-Trihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

m-Isopropylphenol (0.35 g, 2.5 mmol) was added to a solution of 2,2,4-trihydroxy-1H-indene-1,3 (2H) -dione (0.50 g, 2.5 mmol) in ice-cold acetic acid (10 ml) and heated for 4 hours at the boil under reflux. The reaction mixture was diluted in ethyl acetate and washed many times with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.33 g (41%). Melting point: 205-207 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (dd, J = 1.8 Hz, 6.9 Hz, 6H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 3 59 (s, 1H, OH) 4.60 (s, 1H, OH) 6.73 (s, 1H, ArH) 6.88 (dd, J = 1.5 Hz, 7.8 Hz, 1H, ArH ) 6.95 (d, J = 8.1 Hz, 1H, ArH) 7.45 (d, J = 7.2 Hz, 2H, ArH) 7.69 (t, J = 7.8 Hz, 1H, ArH) 8.40 (s, 1H, OH). MS (EI): 312.

<EXAMPLE 44> 4b, 9b-Dihydroxy-7-isopropyl-1H-cyclopenta [b] naphthalene [1,2-b] furan-10 (9bH) -one

m-Isopropylphenol (0.03 g, 0.2 mmol) was added to a solution of 2,2-dihydroxy-1H-cyclopenta [b] naphthalene-1,3 (2H) -dione (50 mg, 0.2 mmol) in ice-cold acetic acid (5 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was concentrated in vacuo, and the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 3) to obtain the title compound. 0.07 g (92%).

Melting point: 186-189 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.09 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.70-2.80 (m, 1H, CH) 6.67 (s, 1H, ArH) 6.76 (d, J = 7.8 Hz, 1H, ArH) 7.41 (d, J = 7.8 Hz, 1H, ArH) 7.48-7.61 (m, 2H, ArH) 7.92 (m, 2H, ArH) 8.26 (s, 1H, ArH) 8.43 (s, 1H, ArH). MS (EI): 346.

<EXAMPLE 45> 9b-Hydroxy-7-isopropyl-4b-methoxy-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Iron (0.09 g, 1.6 mmol), conc. HCl (0.05 ml) and water (0.5 ml) were added in this order to a solution of 4b, 9b-dihydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan -10 (9bH) -one (80 mg, 0.2 mmol) in absolute ethanol (5 ml). The reaction mixture was heated for 2 hours at the boil under reflux. After filtering at high temperature to remove iron, the filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. 80 mg (80%).

Melting point: 181-183 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (dd, J = 2.7 Hz, 6.9 Hz, 6H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 3 73 (s, 3H, OCH ₃ ) 5.56 (s, 1H, OH) 6.59 (d, J = 8.1 Hz, 1H, ArH) 6.73 (s, 1H, ArH) 6.86 (dd, J = 1.5 Hz, 7.8 Hz, 1H, ArH) 7.08 (d, J = 7.2 Hz, 1H, ArH) 7.46 (m, 2H, ArH). MS (EI): 326.

<EXAMPLE 46> 1-amino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Iron (0.48 g, 8.5 mmol), conc. HCl (0.1 ml) and water (1 ml) were added in this order to a solution of 4b, 9b-dihydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.40 g, 1.1 mmol) in absolute ethanol (10 ml). The reaction mixture was heated for 2 hours at the boil under reflux. After removing the iron by high temperature filtration, the residue was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.17 g (47%).

Melting point: 180-182 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (dd, J = 1.8 Hz, 6.9 Hz, 6H, CH ₃ ) 2.79-2.89 (m, 1H, CH) 3 , 57 (s, 1H, OH) 4.57 (s, 1H, OH) 5.55 (s, 2H, NH ₂ ) 6.61 (d, J = 8.1 Hz, 1H, ArH) 6.77 (s, 1H, ArH) 6.85 (dd, J = 1.5 Hz, 7.8 Hz, 1H, ArH) 7.17 (d, J = 7.5 Hz, 1H, ArH) 7.42- 7.52 (m, 2H, ArH). MS (EI): 311.

<EXAMPLE 47> 1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate

Iron (0.22 g, 3.8 mmol), conc. HCl (0.05 ml) and water (1 ml) were added in this order to a solution of 7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b ] furan-4b, 9b-diyl diacetate (0.23 g, 0.5 mmol) in absolute ethanol (10 ml). The reaction mixture was heated for 2 hours at the boil under reflux. After removing the iron by high temperature filtration, the filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.15 g (71%).

Melting point: 220-223 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (dd, J = 6.9 Hz, 2.1 Hz, 6H, CH ₃ ) 2.15 (s, 6H, OAc) 2.81-2 90 (m, 1H, CH) 5.57 (s, 2H, NH ₂ ) 6.64 (d, J = 8.1 Hz, 1H, ArH) 6.75 (s, 1H, ArH) 6.92 (dd, J = 7.8 Hz, 1.2 Hz, 1H, ArH) 7.29 (d, J = 7.8 Hz, 1H, ArH) 7.43-7.51 (m, 2H, ArH) . ¹³ C-NMR (300 MHz, CDCl ₃ ) δ 20.22, 21.40, 23.77, 23.82, 34.37, 87.36, 108.54, 110.02, 113.847, 116.11, 117.79, 118.03, 121.31, 124.89, 137.49, 145.40, 147.37, 154.38, 157.54, 167.18, 169.51, 194.17. MS (EI): 395.

<EXAMPLE 48> N- (4b, 9b-Dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide

1-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate (30 mg, 0.06 mmol) in absolute methanol (2 ml) was reacted with potassium carbonate (0.05 g, 0.3 mmol) at room temperature for 1 hour. The reaction mixture was concentrated in vacuo, diluted in ethyl acetate and washed repeatedly with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 7 mg (35%).

Melting point: 152-154 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (dd, J = 1.9 Hz, 6.7 Hz, 6H, CH ₃ ) 2.16 (s, 3H, NHAc) 2.72-2 81 (m, 1H, CH) 3.76 (s, 1H, OH) 4.60 (s, 1H, OH) 6.65 (s, 1H, ArH) 6.79 (d, J = 8.1 Hz, 1H, ArH) 7.35 (d, J = 7.8 Hz, 1H, ArH) 7.53 (d, J = 7.5 Hz, 1H, ArH) 7.66 (t, J = 8, 1 Hz, 1H, ArH) 8.44 (d, J = 8.1 Hz, 1H, ArH) 9.88 (s, 1H, NH). MS (EI): 353.

<EXAMPLE 49> Methyl-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate

A solution of 4b, 9b-dihydroxy-1-isocyanato-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (50 mg, 0.14 mmol) in absolute methanol ( 5 ml) was heated at reflux for 40 minutes, concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 12 mg (22%).

Melting point: 96-99 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 6.9, 1.8 Hz, 6H, CH ₃ ) 2.77-2.87 (m, 1H, CH) 3, 80 (s, 3H, OCH ₃ ) 6.70 (s, 1H, ArH) 6.84 (d, J = 8.1 Hz, 1H, ArH) 7.41 (d, J = 7.8 Hz, 1H , ArH) 7.54 (d, J = 7.8 Hz, 1H, ArH) 7.71 (t, J = 8.1 Hz, 1H, ArH) 8.23 (d, J = 8.4 Hz, 1H, ArH) 9.37 (s, 1H, NH). MS (EI): 369.

<EXAMPLE 50> 1-amino-7-ethyl-4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

Iron (0.31 g, 5.57 mmol) and conc. HCl (0.05 ml) was added to a solution of 7-ethyl-4b, 9b-dihydroxy-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.25 g 0.76 mmol) in ethanol (5 ml) and water (0.5 ml). After 2 hours of reaction, the reaction mixture was washed with methanol, the filtrate was concentrated and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.05 g (22%).

Melting point: 200-203 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (t, J = 7.5 Hz, 3H, CH ₃ ) 2.57 (q, J = 7.5 Hz, 2H, CH ₂ ) 5 47 (s, 2H, NH ₂ ) 6.61 (d, J = 8.1 Hz, 1H, ArH) 6.66 (s, 1H, ArH) 6.80 (d, J = 7.8 Hz, 1H, ArH) 7.14 (d, J = 7.5 Hz, 1H, ArH) 7.29-7.39 (m, 2H, ArH). MS (EI): 297.

<EXAMPLE 51> 7-Ethyl-4b, 9b-dihydroxy-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

Triethylamine (0.09 g, 0.96 mmol) and methyl chloroformate (0.09 g, 0.96 mmol) were added to the solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro -5-oxa-indeno [2,1-a] inden-10-one (0.10 g, 0.32 mmol) in anhydrous tetrahydrofuran (15 ml) and heated for 14 hours at the boil under reflux. The organic layer was concentrated and purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 80 mg (58%).

Melting point: 110-120 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84-2.89 (m, 1H, CH) 3.71 (s, 3H, OCH ₃ ) 3.76 (s, 3H, OCH ₃ ) 5.67 (s, 2H, NH ₂ ) 6.88-6.93 (m, 2H, ArH) 7.19 (d, J = 8 , 4 Hz, 1H, ArH) 7.25 (d, J = 7.5 Hz, 1H, ArH) 7.56 (t, J = 7.8 Hz, 1H, ArH) 7.66 (d, J = 8.4 Hz, 1H, ArH). MS (EI): 427.

<EXAMPLE 52> 7-Ethyl-2,4b, 9b-trihydroxy-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one

m-Ethylphenol (0.60 g, 4.97 mmol) was added to a solution of 2,2,5-trihydroxy-2H-indene-1,3-dione (0.99 g, 4.97 mmol) in acetic acid (10 ml) and heated for 10 hours at the boil under reflux. The filtrate was concentrated and subjected to column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 1.02 g (69%).

Melting point: 208-213 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (t, J = 7.5 Hz, 3H, CH ₃ ) 2.57 (q, J = 15.0 Hz, 7.5 Hz, 2H , CH ₂ ) 6.64 (s, 3H, ArH) 6.79 (d, J = 7.8 Hz, 1H, ArH) 6.97 (dd, J = 8.5 Hz, 1.9 Hz 1H, ArH) 7.28 (s, 1H, ArH) 7.42 (d, J = 7.8 Hz, 1H, ArH) 7.65 (d, J = 8.5 Hz, 1H, ArH). MS (EI): 298.29.

<EXAMPLE 53> 4b-Acetoxy-1-amino-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester

Triethylamine (0.11 g, 1.16 mmol) was added to the solution of 4b, 9b-dihydroxy-7-isopropyl-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.58 mmol) in anhydrous chloroform (10 ml) at room temperature. Diluted 10% acetyl chloride (1 ml) in chloroform at 0 ° C was slowly added to this reaction mixture and incubated at the same temperature for 1 hour. The reaction mixture was diluted in dichloromethane and washed many times with water. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 30 mg (12%).

Melting point: 201-203 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.21 (dd, J = 8.4 Hz, 2.0 Hz, 6H, CH ₃ ) 2.16 (s, 6H, OAc) 2.85-2 90 (m, 1H, CH) 6.75 (s, 1H, ArH) 6.96 (d, J = 7.9 Hz, 1H, ArH) 7.49 (d, J = 7.9 Hz, 1H , ArH) 7.88-7.91 (m, 2H, ArH) 8.39 (dd, J = 6.7 Hz, 2.0 Hz, 1H, ArH). MS (EI): 425.

<EXAMPLE 54> 4b-Acetoxy-7-isopropyl-1-methanesulfonylamino-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester

Triethylamine (0.05 g, 0.50 mmol) was added to the solution of 4b-acetoxy-1-amino-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b acetic acid ethyl ester (0.10 g, 0.25 mmol) in anhydrous chloroform (10 ml) at room temperature. To this solution methanesulfonyl chloride (0.05 g, 0.50 mmol) was slowly added at 0 ° C and the reaction was carried out at room temperature for 12 hours. The reaction mixture was diluted in dichloromethane and washed many times with water. The organic layer was dried and filtered, followed by purification by column chromatography (ethyl acetate: hexane = 1: 2 to 1: 1) to obtain the title compound. 10 mg (8%).

Melting point: 96-100 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.07 (s, 3H, OAc) 2.20 (s, 3H, OAc) 2.83-2.88 (m, 1H, CH) 3.16 (s, 3H, CH ₃ ) 6.83 (s, 1H, ArH) 7.14 (d, J = 8.1 Hz, 1H, ArH) 7.59 (q, J = 8.1 Hz, 1H, ArH) 7.67 (d, J = 7.5 Hz, 1H, ArH) 7.86 (t, J = 7.5 Hz, 1H, ArH) 7.98 (d, J = 8.1 Hz, 1H, ArH) 9.23 (s, 1H, NH). MS (EI): 473.

<EXAMPLE 55> 1- (4b, 9b-Dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) -3- isopropylurea

Isopropylamine (0.012 ml) was added dropwise to a solution of 4b, 9b-dihydroxy-1-isocyanato-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (40 mg, 0.11 mmol) in anhydrous tetrahydrofuran. The reaction mixture was heated for 12 hours at the boil under reflux, concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 10 mg (21%).

Melting point: 81-85 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.98 (t, J = 7.4 Hz, 6H, CH ₃ ) 1.15-1.32 (m, 6H, CH ₃ ) 2.81-2 85 (m, 1H, CH) 3.78 (s, 1H, OH) 4.14 (t, J = 6.6 Hz, 2H, NH, CH) 4.67 (s, 1H, OH) 6, 72 (s, 1H, ArH) 6.86 (d, J = 7.8 Hz, 1H, ArH) 7.42 (d, J = 7.8 Hz, 1H, ArH) 7.53 (d, J = 7.8 Hz, 1H, ArH) 7.71 (t, J = 8.0 Hz, 1H, ArH) 8.27 (d, J = 8.3 Hz, 1H, ArH) 9.36 (s, 1H , NH). MS (EI): 396.

<EXAMPLE 56> N- (9b-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide

To a solution of N- (4b-chloro-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide (0 53 g, 1.4 mmol) in anhydrous tetrahydrofuran (10 ml) was added 2M ammonia (1.42 ml in isopropyl alcohol) at 5 ° C and the reaction mixture was stirred at room temperature for 2 hours. After concentration in vacuo, the reaction mixture was diluted in dichloromethane and washed with aqueous sodium bicarbonate. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 40 mg (8%).

Melting point: 152-156 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (dd, J = 1.8, 6.9 Hz, 6H, CH ₃ ) 2.23 (s, 3H, CH ₃ ) 2.78-2 87 (m, 1H, CH) 6.70 (s, 1H, ArH) 6.84 (d, J = 7.8 Hz, 1H, ArH) 7.34 (d, J = 7.8 Hz, 1H , ArH) 7.63 (d, J = 7.2 Hz, 1H, ArH) 7.75 (t, J = 8.1 Hz, 1H, ArH) 8.54 (d, J = 8.1 Hz, 1H, ArH) 9.99 (s, 1H, NH). MS (EI): 352.

<EXAMPLE 57> N, N ′ - (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1,9b-diyl) diacetamide

N- (9b-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide (400 mg, 0.11 mmol) was dissolved in anhydrous acetic acid (3 ml) and reacted with anhydrous acetic acid (0.01 g, 0.11 mmol) for 2 hours at 80 ° C. The reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 12 mg (27%).

Melting point: 189-191 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 2.1, 6.9 Hz, 6H, CH ₃ ) 2.03 (s, 3H, CH ₃ ) 2.20 (s , 3H, CH ₃ ) 2.77-2.86 (m, 1H, CH) 5.40 (s, 1H, OH) 6.52 (s, 1H, NH) 6.70 (s, 1H, ArH) 6.84 (dd, J = 1.2, 8.1 Hz, 1H, ArH) 7.29 (d, J = 8.1 Hz, 1H, ArH) 7.57 (d, J = 7.5 Hz , 1H, ArH) 7.72 (t, J = 8.1 Hz, 1H, ArH) 8.54 (d, J = 8.1 Hz, 1H, ArH) 10.00 (s, 1H, NH). MS (EI): 394.

<EXAMPLE 58> N- (7-amino-2-hydroxy-2- (4-isopropyl-2-hydroxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-4-yl) acetamide

Water (1.5 ml), iron (0.71 g) and conc. HCl (0.05 ml) was added in this order to a solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-4-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH ) -one (0.70 g, 1.75 mmol) in ethanol (15 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with methanol, concentrated in vacuo, and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. 0.33 g (51%).

Melting point: 278-280 ° C.

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 1.18 (dd, J = 6.3 Hz, 6H, CH ₃ ) 2.17 (s, 3H, CH ₃ ) 2.78-2.86 (m, 1H, CH) 6.38 (m, 2H, NH, ArH) 6.65 (s, 2H, ArH) 6.83 (d, J = 8.1 Hz, 2H, ArH). MS (EI): 368.

<EXAMPLE 59> N- (2-amino-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl ) acetamide

Water (0.3 ml), iron (0.10 g) and conc. HCl (0.05 ml) was added in this order to a solution of N- (4b, 9b-dihydroxy-7-isopropyl-2-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1, 2-b] furan-1-yl) acetamide (0.10 g, 0.25 mmol) in ethanol (3 ml) and heated for 90 min at the boil under reflux. The reaction mixture was washed with methanol, concentrated in vacuo, and purified by column chromatography (ethyl acetate: hexane = 2: 1) to obtain the title compound. 22 mg (24%).

Melting point: 177-181 ° C.

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 1.16 (d, J = 3.0, 6.9 Hz, 6H, CH ₃ ) 2.30 (s, 3H, CH ₃ ) 2.77 -2.86 (m, 1H, CH) 5.93 (s, 2H, NH ₂ ) 6.62 (s, 1H, ArH) 6.79 (d, J = 7.8 Hz, 1H, ArH) 6 99 (s, 1H, ArH) 7.29-7.40 (m, 2H, ArH) 8.86 (s, 1H, NH).

<EXAMPLE 60> 1-amino-4b, 9b-dihydroxy-7-isopropyl-2-nitro-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

N- (2,2-Dihydroxy-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl) acetamide (0.10 mg, 0.25 mmol) was dissolved in 6 M HCl (1.4 ml) and methanol (1 ml) and heated for 90 min at 90 ° C. This solution was added to sodium carbonate and 2 N. NaOH and was extracted with methylene chloride. The organic layer was concentrated to obtain the title compound. 87 mg (97%).

Melting point: 12-116 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83-2.88 (m, 1H, CH) 4.60 (s, 1H, OH) 6.75 (s, 1H, ArH) 6.90 (d, J = 6.9 Hz, 1H, ArH) 7.19 (d, J = 8.4 Hz, 1H, ArH) 7, 43 (d, J = 8.1 Hz, 1H, ArH) 7.96 (s, 2H, NH ₂ ) 8.56 (d, J = 9.0 Hz, 1H, ArH). MS (EI): 356.

<EXAMPLE 61> 1,4-Diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Water (1.5 ml), iron (0.68 g) and conc. HCl (0.05 ml) was added in this order to a solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-4-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH ) -one (0.60 g, 1.68 mmol) in ethanol (15 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with methanol, concentrated in vacuo, and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.22 g (36%).

Melting point: 223-231 ° C.

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.78-2.82 (m, 1H, CH) 6.56 (s , 1H, ArH) 6.77 (d, J = 8.1 Hz, 1H, ArH) 6.99 (s, 2H, ArH) 7.43 (d, J = 8.1 Hz, 1H, ArH). MS (EI): 326.

<EXAMPLE 62> 1,2-Diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

Water (0.3 ml), iron (0.08 g) and conc. HCl (0.03 ml) was added in this order to a solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-2-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH ) -one (75 mg, 0.21 mmol) in ethanol (3 ml) and heated for 90 min at the boil under reflux. The reaction mixture was washed with methanol, concentrated in vacuo, and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. 12 mg (17%).

Melting point: 163-166 ° C.

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 1.03 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.61-2.70 (m, 1H, CH) 5.46 ( s, 1H, ArH) 6.01 (s, 1H, ArH) 6.51-6.58 (m, 2H, ArH) 6.98 (d, J = 9.0 Hz, 1H, ArH). MS (EI): 326.

<EXAMPLE 63> 2- (2-Hydroxy-4-isopropylphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-yldimethylcarbamate

Dimethylcarbamoyl chloride (0.72 g, 6.7 mmol) and trimethylamine (0.41 g, 4.0 mmol) were added to a solution of 4-dimethylaminopyridine (0.1 g) 4b, 9b-dihydroxy-7-isopropyl-4b, 9b -dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.3 mmol) in anhydrous tetrahydrofuran (10 ml) and heated for 24 hours at the boil under reflux. The reaction product was concentrated and extracted with ethyl acetate. The concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.19 g (15%).

Melting point: 114-118 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (d, J = 6.8 Hz, 6H, CH ₃ ) 2.78-2.91 (m, 4H, CH, NCH ₃ ) 3.06 (s, 3H, NCH ₃ ) 5.57 (s, 1H, OH) 6.72 (s, 1H, ArH) 6.88 (d, J = 7.8 Hz, 1H, ArH) 7.51 (d , J = 8.1 Hz, 1H, ArH) 7.56-7.78 (m, 3H, ArH) 7.99 (d, J = 7.8 Hz, 1H, ArH). MS (EI): 367.

<EXAMPLE 64> 4b, 9b-Dihydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

To a solution of ninhydrin (0.30 g, 1.68 mmol) in acetic acid (10 ml) was added 2,4-diisopropylphenol (0.27 g, 1.51 mmol), then the solution was heated for 12 hours under reflux a refrigerator. After concentration in vacuo, recrystallization from methylene chloride gave the title compound (0.40 g, 70%).

Melting point: 205-206 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.14-1.24 (m, 12H), 2.81 (q, J = 7.2 Hz, 1H), 3.07 (q, J = 7.2 Hz, 1H), 3.65 (s, 1H), 4.55 (s, 1H), 7.00 (d, J = 1.7 Hz, 1H), 7.17 (s, 1H ), 7.54 (d, J = 8.4 Hz, 1H), 7.76-7.81 (m, 2H), 8.00 (d, J = 7.6 Hz, 1H).

<EXAMPLE 65> 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

Oxalyl chloride (0.69 ml, 8.15 mmol) and two drops of dimethylformamide were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (2.00 g, 6.79 mmol) in methylene chloride (20 ml) and stirred at room temperature for 3 hours. Concentration in vacuo afforded 9b-chloro-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one (2.33 g, 109%).

9b-Chloro-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.18 mmol) was dissolved in tetrahydrofuran (10 ml ), cooled to 5 ° C and mixed with 2.0 M ammonia in isopropyl alcohol (3.18 ml, 6.36 mmol) at room temperature for 4 hours with stirring. After concentration in vacuo, purification by column chromatography (ethyl acetate: hexane = 1: 4) gave the title compound (0.75 g, 80%).

Melting point: 151-152 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 1.9 Hz, 7.0 Hz, 6H), 2.81 (q, J = 7.2 Hz, 1H), 6.68 (s, 1H), 6.81 (d, J = 7.8 Hz, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.51 (t, J = 8 , 3 Hz, 1H), 7.73-7.80 (m, 2H), 8.01 (d, J = 7.8 Hz, 1H).

<EXAMPLE 66> N- (4b-Hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) acetamide

Anhydrous acetic acid (0.08 ml, 0.88 mmol) was added to a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.26 g, 0.88 mmol) in acetic acid (5 ml) and heated for 2 hours at the boil under reflux. Concentration in vacuo and recrystallization in methylene chloride gave the title compound (0.25 g, 84%).

Melting point: 183-184 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (d, J = 3.0 Hz, 3H), 1.17 (d, J = 3.0 Hz, 3H), 2.06 (s, 3H), 2.81 (q, J = 7.1 Hz, 1H), 5.73 (s, 1H), 6.70 (d, J = 1.1 Hz, 1H), 6.81 (dd , J = 1.4 Hz, 7.9 Hz, 1H), 7.25 (d, J = 7.2 Hz, 1H), 7.54 (t, J = 8.2 Hz, 1H), 7, 76-7.82 (m, 2H); 7.99 (d, J = 7.7 Hz, 1H).

<EXAMPLE 67> 9b-Hexylamino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

To a solution of 4b, 9b-dihydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] indene-10-one (1.00 g, 3.39 mmol) in methylene chloride (10 ml) oxalyl chloride (0.35 ml, 4.08 mmol) and two drops of dimethylformamide were added, followed by stirring at room temperature for 3 hours. Concentration in vacuo afforded 9b-chloro-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one (1.33 g, 109%).

9b-Chloro-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (1.00 g, 3.18 mmol) was dissolved in tetrahydrofuran (10 ml ), cooled to 5 ° C and reacted with hexylamine (0.84 ml, 6.36 mmol) at room temperature for 3 hours with stirring. Concentration in vacuo and purification by column chromatography (ethyl acetate: hexane = 1: 4) gave the title compound (0.58 g, 48%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.84 (t, J = 7.8 Hz, 3H), 1.15 (d, J = 2.5 Hz, 3H), 1.17 (d, J = 2.7 Hz, 3H), 1.20-1.33 (m, 6H), 1.42-1.52 (m, 2H), 2.45 (t, J = 8.3 Hz, 2H ), 2.81 (q, J = 7.7 Hz, 1H), 6.69 (s, 1H), 6.81 (dd, J = 1.0 Hz, 7.9 Hz, 1H), 7 30 (d, J = 7.6 Hz, 1H), 7.49 (t, J = 8.6 Hz, 1H), 7.73-7.78 (m, 2H), 8.00 (d, J = 7.6 Hz, 1H).

<EXAMPLE 68> 9b-amino-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

To a solution of 4b, 9b-dihydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one (0.30 g, 0.88 mmol) in methylene chloride (10 ml) was added oxalyl chloride (0.35 ml, 4.08 mmol) and two drops of dimethylformamide, followed by reaction at room temperature for 3 hours with stirring. Concentration in vacuo afforded 9b-chloro-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.35 g, 111%).

9b-Chloro-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.35 g, 0.98 mmol) was dissolved in tetrahydrofuran ( 10 ml), cooled to 5 ° C and reacted with 2.0 M ammonia in isopropyl alcohol (0.98 ml, 1.96 mmol) at room temperature for 4 hours. Concentration in vacuo and purification by column chromatography (ethyl acetate: hexane = 1: 2) gave the title compound (0.10 g, 30%).

Melting point: 199-200 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15-1.23 (m, 12H), 2.80 (q, J = 7.3 Hz, 1H), 3.06 (q, J = 7.3 Hz, 1H), 4.43 (s, 2H), 7.00 (d, J = 1.4 Hz, 1H), 7.21 (d, J = 1.6 Hz, 1H), 7.51 (t, J = 9.0 Hz, 1H), 7.73-7.80 (m, 2H), 8.00 (d, J = 6.8 Hz, 1H).

<EXAMPLE 69> 4b-Hydroxy-9b-isocyanato-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.50 g, 1.69 mmol) in toluene (10 ml) triethylamine (0.26 ml, 1.86 mmol) and triphosgene (0.55 g, 1.86 mmol) were added, followed by heating for 3 hours at the boil under reflux. After concentration in vacuo, the concentrate was purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound (0.40 g, 73%).

Melting point: 150-152 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 3.1 Hz, 3H), 1.18 (d, J = 3.1 Hz, 3H), 2.85 (q. , J = 7.4 Hz, 1H), 6.82 (s, 1H), 6.90 (dd, J = 1.0 Hz, 7.9 Hz, 1H), 7.51 (d, J = 8 , 0 Hz, 1H), 7.65 (t, J = 8.6 Hz, 1H), 7.77 (s, 1H), 7.85-7.89 (m, 2H), 8.01 (d , J = 8.0 Hz, 1H).

<EXAMPLE 70> Methyl - ((4b, 9b) -4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-9bH-indeno [1,2-b] benzofuran-9b-yl) carbamate

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.30 g, 1.01 mmol) in tetrahydrofuran (10 ml) triethylamine (0.17 ml, 1.21 mmol) and methyl chloroformate (0.07 ml, 1.01 mmol) were added, followed by reaction at room temperature for 3 hours with stirring.

After vacuum concentration, the concentrate was extracted with water and methylene chloride and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound (30 mg, 8%).

Melting point: 150-152 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (d, J = 3.0 Hz, 3H), 1.17 (d, J = 3.1 Hz, 3H), 2.82 (q. , J = 7.8 Hz, 1H), 3.66 (s, 3H), 5.54 (s, 1H), 5.94 (s, 1H), 6.70 (s, 1H), 6.83 (d, J = 7.5 Hz, 1H), 7.28 (d, J = 7.9 Hz, 1H), 7.55 (t, J = 8.7 Hz, 1H), 7.78-7 84 (m, 2H); 8.01 (d, J = 7.9 Hz, 1H).

<EXAMPLE 71> (9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxa-indeno [2,1-a] inden-4b-yl) pentanoic acid amide

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.30 g, 1.01 mmol) in tetrahydrofuran (10 ml) triethylamine (0.17 ml, 1.21 mmol) and valeroyl chloride (0.12 ml, 1.01 mmol) were added, followed by reaction at room temperature for 1 hour with stirring.

After vacuum concentration, the concentrate was extracted with water and methylene chloride and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound (0.21 g, 55%).

Melting point: 110-112 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.89 (t, J = 8.0 Hz, 3H), 1.15 (d, J = 3.3 Hz, 3H), 1.17 (d, J = 3.1 Hz, 3H), 1.28-1.38 (m, 2H), 1.54-1.64 (m, 2H), 2.30 (t, J = 9.1 Hz, 2H ), 2.82 (q, J = 7.8 Hz, 1H), 5.73 (s, 1H), 6.63 (s, 1H), 6.71 (d, J = 1.3 Hz, 1H), 6.81 (dd, J = 1.1 Hz, 7.9 Hz, 1H), 7.24 (d, J = 7.5 Hz, 1H), 7.55 (t, J = 8, 0 Hz, 1H), 7.77-7.84 (m, 2H), 8.01 (d, J = 7.7 Hz, 1H).

<EXAMPLE 72> N- (9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) isobutylamide

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.30 g, 1.01 mmol) in tetrahydrofuran (10 ml) triethylamine (0.17 ml, 1.21 mmol) and isobutyryl chloride (0.10 ml, 1.01 mmol) were added, followed by reaction at room temperature for 1 hour with stirring.

After vacuum concentration, the concentrate was extracted with water and methylene chloride and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound (0.21 g, 54%).

Melting point: 109-111 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (d, J = 6.7 Hz, 12H), 2.51 (q, J = 7.2 Hz, 1H), 2.82 (q ., J = 7.7 Hz, 1H), 5.73 (s, 1H), 6.63 (s, 1H), 6.71 (s, 1H), 6.81 (d, J = 7.7 Hz, 1H), 7.24 (d, J = 8.3 Hz, 1H), 7.55 (t, J = 8.1 Hz, 1H), 7.76-7.86 (m, 2H), 8.00 (d, J = 7.6 Hz, 1H).

<EXAMPLE 73> N- (1-amino-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide

To a solution of N- (9b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide (0.30 g, 0.78 mmol) in ethanol / water (9 ml / 0.9 ml) was added iron (0.30 g, 5.46 mmol) and one drop conc. HCl, followed by heating for 1 hour at the boil under reflux. After being neutralized with sodium bicarbonate solution, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (0.20 g, 72%).

Melting point: 278-280 ° C.

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 7.0 Hz, 6H), 2.00 (s, 3H), 2.80 (q, J = 7.0 Hz, 1H), 6.61-6.68 (m, 2H), 6.83 (d, J = 7.5 Hz, 1H), 6.97 (d, J = 7.2 Hz, 1H), 7.35 (d, J = 7.8 Hz, 1H); 7.41 (t, J = 9.6 Hz, 1H).

<EXAMPLE 74> N- (9b-Hydroxy-6,8-diisopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide

Anhydrous acetic acid (0.02 ml, 0.20 mmol) was added to a solution of 9b-amino-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10 -one (70 mg, 0.20 mmol) in acetic acid (5 ml) and heated for 2 hours at the boil under reflux. After neutralization with sodium bicarbonate, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (50 mg, 66%).

Melting point: 217-219 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 3.6 Hz, 3H), 1.21 (d, J = 2.4 Hz, 3H), 1.23 (d, J = 5.7 Hz, 3H), 2.20 (s, 3H), 2.85 (q, J = 6.7 Hz, 1H ), 3.06 (q, J = 7.6 Hz, 1H), 7.05 (d, J = 1.7 Hz, 1H), 7.25 (d, J = 1.7 Hz, 1H) 7.56 (t, J = 8.3 Hz, 1H); 7.74-7.82 (m, 2H); 7.96 (d, J = 7.6 Hz, 1H).

<EXAMPLE 75> N- (9b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) -N-methylacetamide

Anhydrous acetic acid (0.03 ml, 0.32 mmol) was added to a solution of 4b-hydroxy-7-isopropyl-9b-methylamino-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.10 g, 0.32 mmol) in acetic acid (5 ml) and heated for 2 hours at the boil under reflux. After neutralization with sodium bicarbonate, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (70 mg, 62%).

Melting point: 216-217 ° C.

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.7 Hz, 6H), 2.13 (s, 3H), 2.75-2.90 (m, 3H) , 6.69 (s, 1H), 6.84 (d, J = 7.6 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.44 (t, J = 8.4 Hz, 1H), 7.64 (t, J = 8.3 Hz, 1H), 7.71 (d, J = 7.6 Hz, 1H), 7.80 (d, J = 7, 6 Hz, 1H).

<EXAMPLE 76> 1- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-4b, 10-dihydro-5-oxa-indeno [2,1-a] inden-9b-yl) -3-isopropylurea

Triphosgene (0.28 g, 0.97 mmol) was added to a solution of 9b-amino-4b-hydroxy-7-isopropyl-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10 -one (0.30 g, 0.88 mmol) in tetrahydrofuran (10 ml) and stirred at room temperature for 2 hours. Concentration in vacuo and purification by column chromatography (ethyl acetate: hexane = 1: 2) gave 4b-hydroxy-9b-isocyanato-7-isopropyl-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a ] inden-10-one (0.20 g, 62%).

4b-Hydroxy-9b-isocyanato-7-isopropyl-1-nitro-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.54 mmol) was dissolved in tetrahydrofuran (10 ml) was added to triethylamine (0.18 ml, 1.30 mmol) and isopropylamine (0.05 ml, 0.65 mmol) and heated for 48 hours at the boil under reflux.

After vacuum concentration, the concentrate was extracted with water and methylene chloride and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (40 mg, 17%).

Melting point: 228-229 ° C.

¹ H-NMR (300 MHz, (CD ₃ ) ₂ CO-d ₆ ) δ 1.00 (d, J = 6.8 Hz, 3H), 1.14 (d, J = 4.5 Hz, 3H) , 1.17 (d, J = 4.5 Hz, 3H), 1.50 (d, J = 6.6 Hz, 3H), 2.78-2.88 (m, 1H), 3.87 ( q, J = 7.2 Hz, 1H), 5.84 (s, 1H), 6.34 (s, 1H), 6.61 (s, 1H), 6.66 (s, 1H), 6 84 (d, J = 7.9 Hz, 1H), 7.46 (d, J = 7.9 Hz, 1H), 7.77 (t, J = 8.5 Hz, 1H), 8.08 (d, J = 7.2 Hz, 1H); 8.19 (d, J = 7.9 Hz, 1H).

<EXAMPLE 77> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) isobutylamide

Iron (0.09 g, 1.70 mmol) and one drop conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) isobutylamide (100 mg, 0.24 mmol) in ethanol / water (3 ml / 0.3 ml) and heated for 1 hour at the boil under reflux. After neutralization with sodium bicarbonate, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (60 mg, 66%).

Melting point: 141-143 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (d, J = 6.7 Hz, 12H), 2.51 (q, J = 7.2 Hz, 1H), 2.83 (q ., J = 7.7 Hz, 1H), 5.60 (s, 2H), 6.67-6.72 (m, 1H), 6.78-6.82 (m, 1H), 6.86 -6.91 (m, 1H), 7.16 (t, J = 7.7 Hz, 1H), 7.22 (d, J = 6.7 Hz, 1H), 7.46 (t, J = 8.8 Hz, 1H).

<EXAMPLE 78> (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) pentanoic acid amide

To a solution of (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) pentanoic acid amide (100 mg, 0, 23 mmol) in ethanol / water (3 ml: 0.3 ml) was added iron (0.09 g, 1.64 mmol). After adding one drop conc. The HCl solution was heated for 1 hour at the boil under reflux. After neutralization with sodium bicarbonate, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (70 mg, 77%).

Melting point: 165-168 ° C.

¹ H-NMR (300 MHz, CD ₃ OD) δ 0.93 (t, J = 8.1 Hz, 3H), 1.17 (d, J = 1.0 Hz, 3H), 1.20 (d , J = 1.0 Hz, 3H), 1.35-1.44 (m, 2H), 1.52-1.63 (m, 2H), 2.28 (t, J = 8.6 Hz, 2H), 2.84 (q, J = 7.1 Hz, 1H), 6.65-6.72 (m, 2H), 6.86 (dd, J = 1.1 Hz, 7.9 Hz , 1H), 6.99 (d, J = 7.4 Hz, 1H), 7.37 (d, J = 7.7 Hz, 1H), 7.43 (t, J = 8.6 Hz, 1H )

<EXAMPLE 79> 9b-Hydroxy-4b- (2-hydroxyethoxy) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Iodine (1.71 g, 6.74 mmol) was added to a solution of 4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (1 g , 3.37 mmol) in ethylene glycol (20 ml) and stirred at room temperature for 3 hours. After the solution was poured into water (100 ml), the solution was extracted with ethyl acetate and the reaction mixture was purified by silica gel column chromatography (40% ethyl acetate in hexane) to obtain the title compound. 0.40 g (39%).

Melting point: 100-105 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.12-1.25 (m, 6H, CH ₃ ), 2.51 (s, 1H, OH, exchanged with D ₂ O) 2.82-2, 86 (sept., 1H, CH), 3.83 (t, 2H, CH ₂ ) 4.04-4.15 (m, 3H, CH ₂ and OH, exchanged with D ₂ O) 6.72 (s, 1H, ArH) 6.87 (d, J = 7.8 Hz, 1H, ArH) 7.42 (d, J = 7.8 Hz, 1H, ArH) 7.57 (t, J = 7.5 Hz , 1H, ArH) 7.92 (t, J = 7.5 Hz, 2H, ArH) 7.94 (d, J = 7.8 Hz, 2H, ArH). MS (EI): 340.

<EXAMPLE 80> 4b, 9b-Dihydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

A solution of 4-nitro-2,3-dihydro-1H-inden-1-one (1.50 g, 8.4 mmol) in 1,4-dioxane (15 ml) and glacial acetic acid (3.5 ml) was added to cesium dioxide (1.87 g, 16.9 mmol) and refluxed at 110 ° C for 2 hours. After filtration, the filtrate was concentrated, mixed with water and extracted with ethyl acetate. The reaction mixture was concentrated to give 2,2-dihydroxy-4-nitro-2H-indene-1,3-dione (600 mg).

In glacial acetic acid (5 ml), 2,2-dihydroxy-4-nitro-2H-indene-1,3-dione (0.50 g, 2.24 mmol) and 3-isopropylphenol (0.37 ml, 2, 7 mmol) was refluxed for 2 hours. The reaction mixture was concentrated and purified by silica gel column chromatography (20% ethyl acetate in hexane) to obtain the title compound as a white solid. 0.30 g (39%).

Melting point: 186-188 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15-1.18 (m, 6H, CH ₃ ) 2.81-2.86 (sept., 1H, CH) 3.53 (s, 1H, OH) 6.24 (s, 1H, OH) 6.71 (s, 1H, ArH) 6.92 (d, J = 7.9 Hz, 1H, ArH) 7.48 (d, J = 7.9 Hz, 1H, ArH) 7.79 (t, J = 8.6 Hz, 1H, ArH) 8.19 (d, J = 7.7 Hz, 1H, ArH) 8.50 (d, J = 7, 1 Hz, 1H, ArH). MS (EI): 341.

<EXAMPLE 81> 4b, 9b-Dihydroxy-7-isopropyl-2,3-dimethoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

To a solution of 5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (1.00 g, 5.2 mmol) in 1,4-dioxane (20 ml) and glacial acetic acid (2 ml) cesium dioxide (1.16 g, 10.4 mmol) was added, followed by reaction at 110 ° C for 2 hours with stirring. The reaction mixture was concentrated, diluted in water and extracted with ethyl acetate to give 0.80 g of 2,2-dihydroxy-5,6-dimethoxy-2H-indene-1,3-dione.

2,2-dihydroxy-5,6-dimethoxy-2H-indene-1,3-dione (0.55 g, 2.30 mmol) in glacial acetic acid (6 ml) and 3-isopropylphenol (1.10 ml, 2.76 mmol) was refluxed for 2 hours. The concentrated reaction mixture was purified by silica gel column chromatography (30% ethyl acetate in hexane) to obtain the title compound. White matter 0.22 g (57%).

Melting point: 127-129 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.81-2.86 (sept., 1H, CH) 3.71 (s , 1H, OH) 3.9 (s, 3H, CH ₃ ) 4.1 (s, 3H, CH ₃ ) 4.6 (s, 1H, OH) 6.72 (s, 1H, ArH) 6.86 (d, J = 7.8 Hz, 1H, ArH) 7.14 (s, 1H, ArH) 7.37-7.43 (m, 2H, ArH). MS (EI): 356.

<EXAMPLE 82> 4b, 9b-Dihydroxy-7-isopropyl-2,3-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

To a solution of 5,6-dimethyl-2,3-dihydro-1H-inden-1-one (0.50 g, 3.12 mmol) in 1,4-dioxane (10 ml) and glacial acetic acid (1 ml) cesium dioxide (0.69 g, 6.24 mmol) was added, followed by reaction at 110 ° C for 2 hours with stirring. The reaction mixture was filtered through a celite pad, and the resulting organic solution was concentrated and purified by silica gel column chromatography (40% ethyl acetate in hexane) to give 2,2-dihydroxy-5,6-dimethyl-2H-indene-1,3- dion. 0.40 g (63%).

2,2-dihydroxy-5,6-dimethyl-2H-indene-1,3-dione (0.35 g, 1.7 mmol) and 3-isopropylphenol (0.28 ml, 2.03 mmol) were dissolved in ice-cold acetic acid (4 ml) and boiled under reflux for 4 hours. The concentrated reaction mixture was purified by silica gel column chromatography (30% ethyl acetate in hexane) to obtain the title compound. White matter 0.39 g (71%).

Melting point: 138-140 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.30 (s, 3H, CH ₃ ) 2.40 (s, 3H, CH ₃ ) 2.77-2.86 (sept., 1H, CH) 3.99 (s, 1H, OH) 4.73 (s, 1H, OH) 6.70 (s, 1H, ArH) 6.81 (d, J = 7.9 Hz, 1H, ArH) 7.39 (d, J = 7.9 Hz, 1H, ArH) 7.53 (s, 1H, ArH) 7.8 (s, 1H, ArH ) MS (EI): 324.

<EXAMPLE 83> Mixture 6: 4 (4bS, 9bS) -2-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one and (4bS, 9bS) -3-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (0.81 g, 3.83 mmol) in 1,4-dioxane (15 ml) and glacial acetic acid (1.5 ml) cesium dioxide (0.94 g, 8.44 mmol) was added, followed by reaction at 110 ° C. for 2.5 hours with stirring. The reaction mixture was filtered through a pad of celite, the filtrate was concentrated and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 5-bromo-2,2-dihydroxy-2H-indene-1,3-dione 0 80 g

5-Bromo-2,2-dihydroxy-2H-indene-1,3-dione (0.70 g, 2.7 mmol) and 3-isopropylphenol (0.45 ml, 3.3 mmol) were dissolved in glacial acetic acid (8 ml) and refluxed for 4 hours. The concentrated reaction mixture was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound as a 6: 4 mixture. White matter 760 mg (75%).

Melting point: 160-162 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.12 (m, 6H, CH ₃ ) 2.72-2.81 (sept., 1H, CH) 5.12 (s, 1H, OH) 5, 60 (s, 1H, OH) 6.63 (d, J = 5.7 Hz, 1H, ArH) 6.75 (d, J = 7.8 Hz, 1H, ArH) 7.32 (d, J = 7.8 Hz, 1H, ArH) 7.49-7.59 (m, 1.3H, ArH) 7.76-7.81 (m, 1H, ArH) 8.11 (s, 0.6H, ArH ) MS (EI): 341.

<EXAMPLE 84> Indeno [2,1-a] inden-4b, 9b (5H, 10H) -diol

A solution of 2,3-dihydro-2- (4-isopropyl-2-methoxyphenyl) -1,3-dioxo-1H-inden-2-ylcarbamate (120 mg, 0.32 mmol) in dichloromethane (5 ml) was added at - 78 ° C for 5 min to a solution of boron tribromide (1.0 M, 0.71 ml, 0.71 mmol) in dichloromethane (3 ml) and stirred at -10 ° C for 3 hours. The reaction mixture was poured into water, extracted with dichloromethane and purified by silica gel column chromatography (30% ethyl acetate in hexane) to obtain the title compound. 90 mg (78%).

Melting point: 161-163 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15-1.18 (m, 6H, CH ₃ ) 2.82 (sept., J = 6.9 Hz, 1H, CH) 3.64 (s , 3H, OCH ₃ ) 5.49 (s, 1H, OH) 5.93 (s, 1H, NH) 6.70 (s, 1H, ArH) 6.82-6.85 (m, 1H, ArH) 7.25-7.29 (m, 1H, ArH) 7.53-7.59 (m, 1H, ArH) 7.79-7.84 (m, 2H, ArH) 8.00-8.03 ( m, 1H, ArH). MS (EI): 353.

<EXAMPLE 85> Isopropyl- (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate

Boron tribromide (1.0 M in dichloromethane, 0.55 ml, 0.55 mmol) was dissolved in dichloromethane (3 ml) and cooled to -78 ° C. To this solution isopropyl-2- (4-isopropyl-2-methoxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-ylcarbamate (100 mg, 0.25) was added dropwise over 5 minutes. mmol) in dichloromethane (5 ml) and stirred at 0 ° C for 4 hours. The reaction mixture was poured into water, extracted with dichloromethane and purified by silica gel column chromatography (30% ethyl acetate in hexane) to obtain the title compound. 45 mg (47%).

Melting point: 114-116 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15-1.18 (m, 12H, CH ₃ ) 2.82 (sept., J = 6.9 Hz, 1H, CH) 4.83 (sept. ., J = 6.3 Hz, 1H, CH) 5.83 (s, 1H, NH) 6.69 (d, J = 1.5 Hz, 1H, ArH) 6.83 (dd, J = 1, 5 Hz, J = 7.8 Hz, 1H, ArH) 7.29 (d, J = 7.8 Hz, 1H, ArH) 7.52-7.58 (m, 1H, ArH) 7.78-7 84 (m, 2H, ArH) 8.01 (d, J = 7.5 Hz, 1H, ArH). MS (EI): 395.

<EXAMPLE 86> Ethyl (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate

Boron tribromide (1.0 M in dichloromethane, 4.3 ml, 4.3 mmol) was dissolved in dichloromethane (15 ml) and cooled to -78 ° C. Ethyl 2- (4-isopropyl-2-methoxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-ylcarbamate (750 mg, 1.96) was added dropwise to this solution over 10 minutes. mmol) in dichloromethane (20 ml) and stirred at 0 ° C for 4 hours. The reaction mixture was poured into water, extracted with dichloromethane and purified by silica gel column chromatography (30% ethyl acetate in hexane) to obtain the title compound. 500 mg (70%).

Melting point: 115-118 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.14-1.17 (m, 9H, CH ₃ ) 2.81 (sept., J = 6.9 Hz, 1H, CH) 4.03-4 09 (m, 2H, OCH ₂ ) 5.67 (br, 1H, OH) 5.92 (br, 1H, NH) 6.68 (s, 1H, ArH) 6.83 (dd, J = 1.5 Hz, J = 8.1 Hz, 1H, ArH) 7.29 (d, J = 8.1 Hz, 1H, ArH) 7.51-7.56 (m, 1H, ArH) 7.76 -7.81 (m, 2H, ArH) 8.00 (d, J = 7.5 Hz, 1H, ArH). MS (EI): 367.

<EXAMPLE 87> N, N ′ - ((4bS, 9bS) -4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 1,9b-diyl) diacetamide

Boron tribromide (1.0 M in dichloromethane, 1.32 ml, 1.32 mmol) was dissolved in dichloromethane (5 ml) and cooled to -78 ° C. To this solution, N, N ′ - (2- (4-isopropyl-2-methoxyphenyl) -1,3-dioxo-2,3-dihydro-1H-indene-2,4-diyl) was added dropwise over 10 minutes) diacetamide (200 mg, 0.49 mmol) in dichloromethane (10 ml) and stirred at room temperature for 12 hours. The reaction mixture was poured into water, extracted with dichloromethane and purified by silica gel column chromatography (ethyl acetate: hexane = 2: 1) to obtain the title compound. 130 mg (67%).

Melting point: 205-207 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (d, J = 6.9 Hz, 6H, CH ₃ ) 1.98 (s, 3H, NAc) 2.19 (s, 3H, NAc) 2.8 (sept., J = 6.9 Hz, 1H, CH) 5.61 (s, 1H, OH) 6.61 (s, 1H, NH) 6.68 (d, J = 1.2 Hz , 1H, ArH) 6.82 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.28 (d, J = 7.8 Hz, 1H, ArH) 7.55 ( dd, J = 0.6 Hz, J = 7.8 Hz, 1H, ArH) 7.66-7.72 (m, 1H, ArH) 8.50 (d, J = 8.4 Hz, 1H, ArH ) 10.03 (s, 1H, NH). MS (EI): 394.

Stage 2: 4b, 5.9b, 10-tetrahydroindeno [2,1-a] inden-4b-ol

Chromium chloride (2.50 g, 16.00 mmol) and nickel chloride (130 mg, 1 mmol) were dissolved in dimethylformamide (25 ml) and stirred at room temperature for 10 minutes. The resulting solution was reacted with a solution of 1- (2-bromobenzyl) -1H-inden-2 (3H) -one (2.50 g, 0.83 mmol) in dimethylformamide (25 ml) at 120-125 ° C for 18 hours. The reaction mixture was poured into water, extracted with diethyl ether and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 10) to obtain the title compound. 0.30 g (16%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.05 (s, 1H, OH) 3.05 (dd, J = 1.5 Hz, J = 16.2 Hz, 1H) 3.56 (d, J = 2.4 Hz, 2H) 3.59-3.67 (m, 1H, CH) 3.87 (d, J = 7.8 Hz, 1H) 7.11-7.26 (m, 7H, ArH) 7.51-7.53 (m, 1H, ArH).

Stage 3: 5,10-Dihydroindeno [2,1-a] inden

4b, 5.9b, 10-Tetrahydroindeno [2,1-a] inden-4b-ol (0.10 g, 0.82 mmol) was dissolved in benzene (5 ml) and a small amount of paratoluene sulfonyl acid was added at room temperature. The reaction mixture was refluxed at 85 ° C for 12 hours until the benzene was completely evaporated, and the residue was separated using silica gel column chromatography (2% ethyl acetate in hexane) to obtain the title compound as a solid. 45 mg (50%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 3.63 (s, 4H, CH ₂ ) 7.16-7.34 (m, 4H, ArH) 7.42-7.53 (m, 4H, ArH )

Stage 4: (4b, 9b) -4b, 5.9b, 10-Tetrahydroindeno [2,1-a] inden-4b, 9b-diol

Osmium tetraoxide (0.02 ml, 0.002 mmol, 2.5% in tert-butanol), potassium ferrocyanide (193 mg, 0.6 mmol), potassium carbonate (81 mg, 0.6 mmol) and quinolidine (2.2 mg, 0.02 mmol) was mixed in a mixture of tert-butanol and water (1: 1, 3 ml), to which was then added a solution of methanesulfonamide (19 mg, 0.2 mmol) and 5,10-dihydroindeno [2,1- a] indene (40 mg, 0.2 mmol) in 1 ml of a mixture of tert-butanol and water (1: 1).

The resulting mixture was stirred for 4.5 hours at room temperature, and then sodium sulfite (0.2 g) was added and stirred for an additional 15 minutes. The reaction mixture was poured into water, extracted with diethyl ether, concentrated and purified by silica gel column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. White matter 25 mg (54%).

Melting point: 157-159 ° C.

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.89 (s, 2H, OH) 3.40 (q, J = 16.8 Hz, J = 8.4 Hz, 4H, CH ₂ ) 7, 13-7.28 (m, 6H, ArH) 7.50-7.53 (m, 2H, ArH). MS (EI): 238.

<EXAMPLE 88> O-Methyloxime 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

To a solution of 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (1.00 g, 3.37 mmol) in anhydrous pyridine (1 ml) was added hydrochloride O-methyl hydroxylamine (564 mg, 6.75 mmol), followed by reaction at room temperature for 3 hours with stirring. After removal of the pyridine solvent, extraction was performed with DCM and water, and the concentrated organic layer was separated and purified by silica gel column chromatography (30% ethyl acetate mixed with 30% hexane) to obtain the title compound. 70 mg (30%).

¹ H-NMR (300 MHz, DMSO) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.79 (sept., J = 6.9 Hz, 1H, CH) 3.9 (s, 3H, N-OCH ₃ ) 6.44 (s, 1H, ArH / OH) 6.64 (s, 1H, ArH) 6.75 (d, J = 7.8 Hz, 1H, ArH) 7 54 (d, J = 7.8 Hz, 1H, ArH) 7.71-7.76 (m, 1H, ArH) 7.84-7.88 (m, 2H, ArH) 8.40 (d, J = 8.1 Hz, 1H, ArH) 9.25 (s, 1H, OH / NH).

<EXAMPLE 89> 9b-Butyrylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxa-indeno [2,1-a] inden-4b-yl ester of butyric acid

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride ( 10 ml) triethylamine (0.20 g, 2.01 mmol) and butyryl chloride (0.18 g, 1.69 mmol) were added at room temperature, followed by reaction for 3 hours with stirring. The reaction product was concentrated and extracted with ethyl acetate, after which the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 50 mg (17%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.90-1.00 (m, 6H, CH ₃ ) 1.18 (dd, J = 2.7, 6.9 Hz, 6H, CH ₃ ) 1 50-1.72 (m, 4H, CH ₂ ) 2.02-2.30 (m, 2H, CH ₂ ) 2.33-2.54 (m, 2H, CH ₂ ) 2.79-2, 88 (m, 1H, CH) 6.00 (s, 1H, NH) 6.67 (s, 1H, ArH) 6.90 (d, J = 8.1 Hz, 1H, ArH) 7.44 (d , J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 7.5 Hz, 1H, ArH) 7.76 (t, J = 7.5 Hz, 1H, ArH) 7.85 ( d, J = 7.8 Hz, 1H, ArH) 7.93 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 90> [2- (2-Hydroxy-4-isopropylphenyl) -1,3-dioxo-indan-2-yl] octanoic acid amide

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride ( 10 ml) triethylamine (0.20 g, 2.01 mmol) and octanoyl chloride (0.27 g, 1.67 mmol) were added, followed by reaction at room temperature for 28 hours with stirring. The reaction product was concentrated and extracted with ethyl acetate, after which the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 6 to 1: 4) to obtain the title compound as a syrup. 0.13 g (45%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.84-0.88 (m, 3H, CH ₃ ) 1.17 (dd, J = 3.0, 6.9 Hz, 6H, CH ₃ ) 1 , 26-1.29 (m, 12H, CH ₂ ) 1.58-1.65 (m, 4H, CH ₂ ) 2.31 (t, J = 7.2 Hz, 2H, CH ₂ ) 2.77 -2.86 (m, 1H, CH) 5.71 (s, 1H, OH) 6.62 (s, 1H, NH) 6.71 (s, 1H, ArH) 6.81 (d, J = 7 8 Hz, 1H, ArH) 7.24 (d, J = 7.8 Hz, 1H, ArH) 7.55 (t, J = 7.8 Hz, 1H, ArH) 7.78-7.84 ( m, 2H, ArH) 8.00 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 91> 9b-Hexanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of hexanoic acid

To a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride ( 10 ml) triethylamine (0.20 g, 2.01 mmol) and hexanoyl chloride (0.22 g, 1.69 mmol) were added, followed by reaction for 5 hours at room temperature with stirring. The reaction product was concentrated and extracted with ethyl acetate, after which the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 6 to 1: 4) to obtain the title compound. 15 mg (4%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.79-0.89 (m, 6H, CH ₃ ) 1.17 (dd, J = 2.7, 6.9 Hz, 6H, CH ₃ ) 1 22-1.33 (m, 8H, CH ₂ ) 1.40-1.65 (m, 4H, CH ₂ ) 2.04-2.55 (m, 4H, CH ₂ ) 2.82-2, 91 (m, 1H, CH) 6.00 (s, 1H, NH) 6.67 (s, 1H, ArH) 6.91 (d, J = 8.1 Hz, 1H, ArH) 7.44 (d , J = 8.1 Hz, 1H, ArH) 7.56 (t, J = 7.5 Hz, 1H, ArH) 7.74-7.89 (m, 2H, ArH) 7.93 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 92> 9b-Heptanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of heptanoic acid

Triethylamine (0.20 g, 2.01 mmol) and heptanoyl chloride (0.25 g, 1.69 mmol) were added at room temperature to a solution of 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5 -oxaidendeno [2,1-a] inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride (10 ml) and stirred for 3 hours. The reaction product was concentrated and extracted with ethyl acetate, after which the concentrated organic layer was purified by column chromatography (ethyl acetate: hexane = 1: 6 to 1: 4) to obtain the title compound. 0.14 g (40%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.84-0.88 (m, 6H, CH ₃ ) 1.17 (dd, J = 2.4, 6.9 Hz, 6H, CH ₃ ) 1 25-1.44 (m, 14H, CH ₂ ) 1.59-1.64 (m, 2H, CH ₂ ) 2.06-2.52 (m, 4H, CH ₂ ) 2.79-2, 86 (m, 1H, CH) 5.98 (s, 1H, NH) 6.74 (s, 1H, ArH) 6.91 (d, J = 7.8 Hz, 1H, ArH) 7.44 (d , J = 8.1 Hz, 1H, ArH) 7.56 (t, J = 7.5 Hz, 1H, ArH) 7.76 (t, J = 7.5 Hz, 1H, ArH) 7.85 ( d, J = 7.8 Hz, 1H, ArH) 7.92 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 93> N - ((4bS, 9bS) -1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl ) octanamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) octanamide (130 mg, 0.28 mmol) was dissolved in ethanol: water (9: 1, 13 ml), iron powder (118 mg, 2.12 mmol) and conc. HCl (3 drops) and heated for 3 hours at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo, separated and purified by silica gel column chromatography (30% ethyl acetate, 1% triethylamine in hexane) to obtain the title compound. 115 mg (96%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.86 (t, J = 6.6 Hz, 3H, CH ₃ ) 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 1, 25 (m, 8H, CH ₂ ) 1.59 (t, J = 6.9 Hz, 2H, CH ₂ ) 2.51 (t, J = 6.9 Hz, 2H, CH ₂ ) 2.81 (sept ., J = 6.9 Hz, 1H, CH) 5.66 (br, 2H, NH ₂ ) 6.62 (m, 2H, ArH) 6.73-6.79 (m, 2H, ArH) 7 13-7.16 (m, 1H, ArH) 7.39-7.45 (t, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 94> (4bR, 9bS) -1-amino-7-isopropyl-10-oxo-9b-propionamido-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpropionate

(4bR, 9bS) -7-Isopropyl-1-nitro-10-oxo-9b-propionamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpropionate (130 mg 0.29 mmol) was dissolved in ethanol: water (9: 1, 10 ml), iron powder (122 mg, 2.18 mmol) and conc. HCl (3 drops) and heated for 1 hour at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo, separated and purified by silica gel column chromatography (30% ethyl acetate, 1% triethylamine in hexane) to obtain the title compound. 60 mg (50%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.05-1.20 (m, 12H, CH ₃ ) 2.10-2.51 (m, 4H, CH ₂ ) 2.85 (sept., J = 6.9 Hz, 1H, CH) 4.41 (br, 2H, NH ₂ ) 5.99 (br, 1H, NH) 6.73 (s, 1H, ArH) 6.89-6.96 (m, 2H, ArH) 7.22-7.34 (m, 2H, ArH) 7.43 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 95> (4bR, 9bS) -1-amino-9b-butyramido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylbutyrate

(4bR, 9bS) -9b-Butyramido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylbutyrate (220 mg , 0.46 mmol) was dissolved in ethanol: water (9: 1, 10 ml), iron powder (195 mg, 3.48 mmol) and conc. HCl (5 drops) was heated for 1 hour at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo, separated and purified by silica gel column chromatography (30% ethyl acetate, 1% triethylamine in hexane) to obtain the title compound. 100 mg (49%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.90-0.99 (m, 6H, CH ₃ ) 1.16-1.19 (m, 6H, CH ₃ ) 1.50-1.77 ( m, 4H, CH ₂ ) 2.04-2.50 (m, 4H, CH ₂ ) 2.85 (sept., J = 6.9 Hz, 1H, CH) 4.40 (br, 2H, NH ₂ ) 5.97 (br, 1H, NH) 6.71 (s, 1H, ArH) 6.71-6.97 (m, 2H, ArH) 7.22-7.35 (m, 2H, ArH ) 7.41 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 96> 1-amino-7-isopropyl-10-oxo-9b-pentanamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpentanoate

To a solution of 7-isopropyl-1-nitro-10-oxo-9b-pentanamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpentanoate (0.287 g, 0.55 mmol) in ethanol (10 ml) was added 1 ml of water, iron powder (0.22 g, 4.01 mmol) and conc. HCl (0.05 ml), followed by heating for 1.5 hours at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo, separated and purified by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) to obtain the title compound. 0.12 g (46%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.89 (m, 6H, CH ₃ ) 1.17 (dd, J = 2.4, 6.9 Hz, 6H, CH ₃ ) 1.23-1 48 (m, 4H, CH ₂ ) 1.50-1.65 (m, 4H, CH ₂ ) 2.04-2.37 (m, 2H, CH ₂ ) 2.40-2.54 (m, 2H, CH ₂ ) 2.80-2.89 (m, 1H, CH) 4.39 (s, 2H, NH ₂ ) 5.91 (s, 1H, NH) 6.71 (s, 1H, ArH) 6.88-6.96 (m, 2H, ArH) 7.22-7.34 (m, 2H, ArH) 7.46 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 97> 1-amino-9b-hexanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylhexanoate

9b-Hexanamido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylhexanoate (0.17 g, 0.32 mmol) was dissolved in ethanol (15 ml), 1.5 ml of water, iron powder (0.13 g, 2.3 mmol) and conc. HCl (0.05 ml) and heated for 1 hour at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo, separated and purified by column chromatography (ethyl acetate: hexane = 1: 6 to 1: 4) to obtain the title compound. 0.15 g (90%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.77-0.93 (m, 6H, CH ₃ ) 1.20 (dd, J = 3.6, 6.9 Hz, 6H, CH ₃ ) 1 23-1.39 (m, 8H, CH ₂ ) 1.50-1.62 (m, 4H, CH ₂ ) 2.04-2.51 (m, 4H, CH ₂ ) 2.80-2, 86 (m, 1H, CH) 4.40 (s, 2H, NH ₂ ) 5.97 (s, 1H, NH) 6.72 (s, 1H, ArH) 6.88-7.06 (m, 2H , ArH) 7.22-7.34 (m, 2H, ArH) 7.43 (d, J = 7.6 Hz, 1H, ArH).

<EXAMPLE 98> (4bS, 9bS) -4b-Hydroxy-7-isopropyl-9b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

Anhydrous methanol (0.1 ml) was slowly added at 0 ° C over 5 minutes to a solution of (4bS, 9bS) -9b-chloro-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (0.30 g, 0.95 mmol) in anhydrous THF (10 ml). After the reaction for 3 hours, the reaction mixture was concentrated, separated and purified by silica gel column chromatography (30% ethyl acetate in 20% hexane) to obtain the title compound. 50 mg (17%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (dd, J = 2.4 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz , 1H, CH) 3.70 (s, 3H, OCH ₃ ) 4.51 (s, 1H, OH) 6.72 (s, 1H, ArH) 6.85 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.49 (d, J = 7.8 Hz, 1H, ArH) 7.52-7.58 (m, 1H, ArH) 7.77-7.82 (m , 2H, ArH) 7.98 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 99> 1-amino-9b-heptanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylheptanoate

9b-Heptanamido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylheptanoate (0.28 g, 0.50 mmol) was dissolved in ethanol (10 ml), 1 ml of water, iron powder (0.20 g, 3.7 mmol) and conc. HCl (0.05 ml) and heated for 1 hour at the boil under reflux. Then the reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 6 to 1: 4) to obtain the title compound. 0.15 g (90%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.79-0.97 (m, 6H, CH ₃ ) 1.19 (dd, J = 3.7, 6.9 Hz, 6H, CH ₃ ) 1 25-1.39 (m, 12H, CH ₂ ) 1.59-1.68 (m, 2H, CH ₂ ) 2.08-2.30 (m, 4H, CH ₂ ) 2.36-2, 54 (m, 2H, CH ₂ ) 2.84-2.89 (m, 1H, CH) 4.42 (s, 2H, NH ₂ ) 5.98 (s, 1H, NH) 6.74 (s, 1H, ArH) 6.91-6.98 (m, 2H, ArH) 7.24-7.37 (m, 2H, ArH) 7.43 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 100> 1 - ((4bS, 9bS) -7-Isopropyl-4b-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea

Concentrated HCl (1 ml) was added to a solution of (4bS, 9bR) -7-isopropyl-10H-4b, 9b- (epiminomethanoimino) indeno [1,2-b] benzofuran-10,12-dione (0.20 g, 0.625 mmol) in methanol (10 ml) and stirred at room temperature. After the reaction, the reaction mixture was concentrated for 2.5 hours, extracted with ethyl acetate and water, and then concentrated to dryness in vacuo. Purified by silica gel column chromatography (5% MeOH in DCM, 1% TEA) to give the title compound. (80 mg, 38%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.75 (sept., J = 6.9 Hz, 1H, CH) 3 68 (s, 3H, CH ₃ ) 6.50 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 6.68 (s, 1H, ArH) 6.76 (d, J = 7.8 Hz, 1H, ArH) 7.35-7.53 (m, 3H, ArH) 7.83 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 101> 1 - ((4bS, 9bS) -4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- urea methyl

To the solution of (4bS, 9bS) -9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.10 g, 0, 34 mmol) in anhydrous THF (2 ml) was added methyl isocyanate (32 μl, 0.51 mmol). After the reaction for 1 hour, the reaction mixture was concentrated and purified by silica gel column chromatography (5% MeOH in DCM, 1% TEA) to obtain the title compound. 50 mg (42%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.78-2.89 (m, 4H, NMe, CH) 6.63 ( s, 1H, ArH) 6.86 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.43 (d, J = 7.8 Hz, 1H, ArH) 7.56 (broad, 2H, ArH) 7.81 (broad, 2H, ArH).

<EXAMPLE 102> 1-Ethyl-3 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl )urea

To a solution of (4bS, 9bS) -9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.10 g, 0, 34 mmol) in anhydrous THF (5 ml) was added ethyl isocyanate (45 μl, 0.85 mmol). After the reaction for 1 hour, the reaction mixture was concentrated and purified by silica gel column chromatography (5% MeOH in DCM, 1% TEA) to obtain the title compound. 60 mg (19%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.04 (t, J = 7.2 Hz, 3H, CH ₃ ) 1.20 (dd, J = 2.4 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz, 1H, CH) 3.36-3.51 (m, 2H, CH ₂ ) 6.62 (d, J = 1.2 Hz , 1H, ArH) 6.85 (dd, J = 1.2 Hz, J = 8.1 Hz, 1H, ArH) 7.46 (d, J = 8.1 Hz, 1H, ArH) 7.52- 7.62 (m, 2H, ArH); 7.68-7.70 (m, 1H, ArH); 7.77-7.98 (m, 1H, ArH).

<EXAMPLE 103> 1 - ((4bS, 9bS) -4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- methoxyurea

Boron tribromide (1.0 M solution in DCM, 1.72 ml, 1.72 mmol) was dissolved in anhydrous DCM (10 ml) and cooled to -80 ° C. To this solution, a solution of 1- (2- (4-isopropyl-2-methoxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-yl) -3-methoxyurea (300 mg, 0 78 mmol) in anhydrous DCM (15 ml). The reaction mixture was left for 10 min at -80 ° C and stirred for 3 hours at 0 ° C. Then the reaction mixture was extracted with DCM and water, dried and concentrated in vacuo. Purified by silica gel column chromatography (5% MeOH in DCM, 1% TEA) and obtained as the title compound. 110 mg (38%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 3, 88 (s, 3H, OCH ₃ ) 6.64 (d, J = 1.2 Hz, 1H, ArH) 6.85 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.37 (d, J = 7.8 Hz, 1H, ArH) 7.55-7.60 (m, 1H, ArH) 7.66-7.71 (m, 1H, ArH) 7.78-7 84 (m, 2H, ArH).

<EXAMPLE 104> 5-Acetyl-4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indole-10 (9bH) -one

N- (3,4-Dimethylphenyl) acetamide (300 mg, 1.84 mmol) and ninhydrin (328 mg, 1.84 mmol) were dissolved in dilute sulfuric acid (6 ml) and stirred at room temperature for 5.5 hours . The reaction was stopped by slowly pouring a solution into 150 g of ice and stirring. The reaction mixture was washed twice with ethyl acetate (70 ml) and the organic layer was washed again with water and brine. The solution was dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography (ethyl acetate: hexane = 1: 1), followed by recrystallization from ethyl acetate / hexane to give the title compound. 60 mg (10%).

¹ H-NMR (300 MHz, DMSO) δ 2.13 (s, 6H, CH ₃ ) 2.74 (s, 3H, NAc) 6.84 (s, 1H, ArH) 7.16 (s, 1H, ArH) 7.49 (br, 1H, ArH) 7.56-7.61 (m, 1H, ArH) 7.63-7.71 (m, 1H, ArH) 7.80-7.89 (m , 2H, ArH) 8.01-8.05 (m, 1H, ArH).

<EXAMPLE 105> 4b, 9b-Dihydroxy-7,8-dimethyl-5-propinoyl-4b, 5-dihydroindeno [1,2-b] indole-10 (9bH) -one

Ten drops of concentrated HCl were added to a solution of N- (2- (2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl) -4,5-dimethylphenyl) propionamide (0.20 g ) in anhydrous THF (10 ml) and stirred. After the reaction for 5 hours, the reaction mixture was poured into ice water to stop the reaction. Before concentration in vacuo, extraction was performed with ethyl acetate and water. The concentrate was purified by column chromatography (30% ethyl acetate mixed with 50% hexane) to give the title compound. 40 mg (20%).

¹ H-NMR (300 MHz, DMSO) δ 1.26 (t, J = 7.5 Hz, 3H, CH ₃ ) 2.14 (s, 6H, CH ₃ ) 3.06-3.58 (m, 2H, CH ₂ ) 6.84 (s, 1H, ArH / OH) 7.16 (s, 1H, ArH / OH) 7.48 (s, 1H, ArH / OH) 7.56-7.61 (m , 1H, ArH) 7.70 (d, J = 7.8 Hz, 1H, ArH) 7.80-7.86 (m, 2H, ArH) 7.95-8.01 (m, 1H, ArH) .

<EXAMPLE 106> 4b, 9b-Dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one

Concentrated HCl (1 ml) was added to a solution of N- (2- (2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl) -4,5-dimethylphenyl) acetamide (0, 10 g) in methanol (10 ml) and stirred overnight to concentrate. The concentrate was washed with sat. NaHCO ₃ was extracted with ethyl acetate and water and concentrated in vacuo to give the title compound (50 mg, 58%).

¹ H-NMR (300 MHz, DMSO) δ 2.33 (s, 3H, CH ₃ ) 2.36 (s, 3H, CH ₃ ) 7.30 (s, 1H, ArH) 7.49 (s, 1H , ArH) 7.55 (t, J = 7.8 Hz, 1H, ArH) 7.94 (t, J = 7.8 Hz, 1H, ArH) 8.03 (d, J = 7.8 Hz, 1H, ArH) 8.25 (d, J = 7.8 Hz, 1H, ArH) 11.70 (br, 1H, NH).

<EXAMPLE 107> 5-Acetyl-7,8-dimethyl-10-oxo-4b, 5.9b, 10-tetrahydroindeno [1,2-b] indole-4b, 9b-diyl diacetate

Acetyl chloride (0.33 ml, 4.64 mmol) and triethylamine (0.65 ml, 4.64 mmol) were slowly added at room temperature to a solution of 5-acetyl-4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indole-10 (9bH) -one (300 mg, 0.93 mmol) in anhydrous THF (20 ml). After stirring at room temperature for 24 hours, the solid thus formed was washed with THF and filtered. After THF was removed, purification by column chromatography (30% ethyl acetate was stirred with 30% hexane) gave the title compound as a yellowish solid. 150 mg (40%).

¹ H-NMR (300 MHz, DMSO) δ 2.06 (s, 3H, OAc) 2.10 (s, 3H, OAc) 2.22-2.23 (s, 6H, CH ₃ ) 2.47 ( s, 3H, NAc) 7.23 (s, 1H, ArH) 7.37 (s, 1H, ArH) 7.64-7.69 (t, 1H, ArH) 7.75 (d, J = 7, 2 Hz, 1H, ArH) 7.87-7.92 (m, 1H, ArH) 8.33 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 108> 5-Acetyl-9b-amino-4b-hydroxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one

AIBN (0.1 g) and SO ₂ Cl ₂ (0.72 g, 5.3 mmol) were added to a solution of N- [2- (1,3-dioxo-indan-2-yl) phenyl] acetamide (1, 00 g, 3.5 mmol) in CCl ₄ (20 ml) and heated under reflux for 3 hours. The solution was concentrated in vacuo, extracted with CH ₂ Cl ₂ , dried, filtered and concentrated in vacuo. Purification by column chromatography (ethyl acetate: hexane = 1: 4 to 1: 2) gave the title compound. 0.60 g (53%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 2.64 (s, 3H, CH ₃ ) 7.19 (t, J = 1.5, 8.4 Hz, 1H, ArH) 7.37 (t, J = 1.5, 8.4 Hz, 1H, ArH) 7.55 (t, J = 7.2 Hz, 1H, ArH) 7.73-7.83 (m, 3H, ArH) 8.20 ( d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 109> N- (9b-amino-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl ) acetamide

To a solution of N- (9b-chloro-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl) acetamide (3.90 g, 9.3 mmol) in anhydrous THF (40 ml) was added 2M NH ₃ in IPA (9.36 ml) at 5 ° C, followed by stirring overnight at room temperature. After removing the solvent by concentration in vacuo, the residue was diluted in methylene chloride and washed with aqueous sodium bicarbonate, bringing the pH to 8.0. The organic layer was dried, filtered and concentrated in vacuo to give the title compound. 3.98 g (107%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 6.9, 2.7 Hz, 6H, CH ₃ ) 2.29 (s, 3H, CH ₃ ) 2.78-2 87 (sept., 1H, CH) 6.71 (s, 1H, ArH) 6.88 (dd, J = 8.1, 2.1 Hz, 1H, ArH) 7.37 (d, J = 7 8 Hz, 1H, ArH) 8.48 (d, J = 9.3 Hz, 1H, ArH) 8.75 (d, J = 9.3 Hz, 1H, ArH) 10.67 (s, 1H, NH).

<EXAMPLE 110> 1,9b-bis-Acetylamino-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of acetic acid

To a solution of N- (9b-amino-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl) acetamide (0.55 g, 1.38 mmol) in anhydrous methylene chloride (20 ml) was added triethylamine (0.21 g, 2.76 mmol) and AcCl (0.20 g, 2.07 mmol) at 0 ° C, s followed by stirring overnight at room temperature. The reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.17 g (26%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19 (dd, J = 3.6, 6.9 Hz, 6H, CH ₃ ) 2.00 (s, 3H, CH ₃ ) 2.17 (s , 3H, CH ₃ ) 2.25 (s, 3H, CH ₃ ) 2.83-2.92 (m, 1H, CH) 6.15 (s, 1H, NH) 6.71 (s, 1H, ArH ) 6.98 (d, J = 7.8 Hz, 1H, ArH) 7.43 (d, J = 7.8 Hz, 1H, ArH) 8.50 (d, J = 9.0 Hz, 1H, ArH) 8.83 (d, J = 9.3 Hz, 1H, ArH) 10.72 (s, 1H, NH).

<EXAMPLE 111> 9b-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate

To N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide (0.50 g, 1 , 48 mmol) was added 10 ml of THF, Et ₃ N (0.24 ml, 1.77 mmol) and methyl chloroformate (0.11 ml, 1.48 mmol) in this order, then this solution was stirred at room temperature for 12 hours.

The reaction mixture was concentrated, extracted with H ₂ O and CH ₂ Cl ₂ and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 20 mg (3%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 2.6 Hz, 3H), 1.18 (d, J = 2.6 Hz, 3H), 2.17 (s, 3H), 2.84 (q, J = 7.8 Hz, 1H), 3.62 (s, 3H), 5.40 (s, 1H), 6.68 (s, 1H), 6.91 (d, J = 7.7 Hz, 1H), 7.44 (d, J = 8.1 Hz, 1H), 7.58 (t, J = 8.5 Hz, 1H), 7.78 (t , J = 8.1 Hz, 1H), 7.87 (d, J = 7.7 Hz, 1H), 7.98 (d, J = 8.1 Hz, 1H).

<EXAMPLE 112> 9b-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpentanoate

To N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide (0.50 g, 1 , 48 mmol) was added 10 ml of THF, Et ₃ N (0.24 ml, 1.77 mmol) and valeroyl chloride (0.18 ml, 1.48 mmol) in this order, followed by stirring the solution at room temperature for 12 hours . After concentration, the concentrate was extracted with H ₂ O and CH ₂ Cl ₂ and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. (30 mg, 5%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.91 (t, J = 7.4 Hz, 3H), 1.16 (d, J = 2.6 Hz, 3H), 1.18 (d, J = 2.6 Hz, 3H), 1.33-1.40 (m, 2H), 1.56-1.64 (m, 2H), 1.95 (s, 3H), 2.35-2 55 (m, 2H), 2.84 (q, J = 7.6 Hz, 1H), 6.10 (s, 1H), 6.68 (d, J = 0.9 Hz, 1H), 6.91 (dd, J = 1.3 Hz, 7.8 Hz, 1H), 7.44 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 8.0 Hz, 1H), 7.77 (t, J = 8.2 Hz, 1H), 7.84 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 7.8 Hz, 1H) .

<EXAMPLE 113> 9b-Acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate

To 9b-acetamido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylmethyl carbonate (50 mg, 0.11 mmol ) EtOH was added: H ₂ O = 2 ml: 0.2 ml, Fe (40 mg, 0.79 mmol) and one drop conc. HCl followed by refluxing for 1 hour.

After neutralizing with NaHCO ₃ , the reaction mixture was purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. (25 mg, 55%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (d, J = 2.6 Hz, 3H), 1.19 (d, J = 2.6 Hz, 3H), 2.18 (s, 3H), 2.85 (q, J = 7.7 Hz, 1H), 3.63 (s, 3H), 4.44 (s, 2H), 6.72 (s, 2H), 6.90 (d, J = 7.8 Hz, 1H), 6.97 (d, J = 7.7 Hz, 1H), 7.23-7.25 (m, 1H), 7.34 (d, J = 7.9 Hz, 1H); 7.41 (d, J = 7.9 Hz, 1H).

<EXAMPLE 114> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) pivalamide

Iron powder (0.04 g, 0.85 mmol), conc. HCl (0.05 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) pivalamide (50 mg, 0.11 mmol) in absolute ethanol (5 ml). The reaction mixture was heated for 2 hours at the boil under reflux. Then the iron powder was filtered off, the filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. (40 mg, 86%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16-1.19 (m, 15H, CH ₃ ) 2.71-2.92 (m, 1H, CH) 6.66 (s, 1H, ArH ) 6.81 (d, J = 7.2 Hz, 1H, ArH) 6.93-7.01 (m, 2H, ArH) 7.11-7.25 (m, 1H, ArH) 7.38- 7.47 (m, 1H, ArH).

<EXAMPLE 115> 9b-Acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylbutyl carbonate

Iron powder (0.09 g, 1.66 mmol), conc. HCl (0.05 ml) and water (0.5 ml) were added in this order to a solution of 9b-acetamido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl-butyl carbonate (0.11 g, 0.22 mmol) in absolute ethanol (5 ml). The reaction mixture was heated for 1.5 hours at the boil under reflux. Then the iron powder was filtered off, the filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound (50 mg, 50%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.89 (t, J = 7.5 Hz, 3H, CH ₃ ) 1.18 (dd, J = 2.4 Hz, 6.9 Hz, 3H, CH ₃ ) 1.28-1.43 (m, 2H, CH ₂ ) 1.56-1.68 (m, 2H, CH ₂ ) 1.96 (s, 3H, CH ₃ ) 2.81-2, 90 (m, 1H, CH) 4.07-4.20 (m, 2H, OCH ₂ ) 6.11 (s, 1H, NH) 6.76 (s, 1H, ArH) 6.94 (t, J = 7.8 Hz, 2H, ArH) 7.22-7.35 (m, 2H, ArH) 7.46 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 116> 9b-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl-ethyl carbonate

Ethyl chloroformate (0.32 g, 3.11 mmol) and trimethylamine (0.25 g, 2.48 mmol) were added to a solution of 9b-chloro-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.70 g, 2.07 mmol) in anhydrous THF (15 ml) and stirred for 4 hours. After THF was removed by concentration in vacuo, the concentrate was diluted in methylene chloride and washed many times with water. The organic layer was dried, filtered and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 14 mg (1.6%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16-1.18 (m, 9H, CH ₃ ) 2.17 (s, 3H, CH ₃ ) 2.82-2.86 (m, 1H, CH) 4.05-4.13 (m, 2H, OCH ₂ ) 5.34 (s, 1H, NH) 6.68 (s, 1H, ArH) 6.91 (d, J = 7.5 Hz, 1H, ArH) 7.44 (d, J = 6.9 Hz, 1H, ArH) 7.58 (t, J = 6.9 Hz, 1H, ArH) 7.79-7.86 (m, 2H, ArH) 7.98 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 117> 9b-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl pivalate

Pivaloyl chloride (0.26 g, 2.22 mmol) and trimethylamine (0.18 g, 1.77 mmol) were added to a solution of 9b-chloro-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.50 g, 1.48 mmol) in anhydrous THF (15 ml) and heated for 18 hours at the boil under reflux. After THF was removed by concentration in vacuo, the residue was diluted in methylene chloride and washed many times with water. The organic layer was dried, filtered and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.13 g (20%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16-1.19 (m, 15H, CH ₃ ) 2.17 (s, 3H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 6.11 (s, 1H, NH) 6.68 (s, 1H, ArH) 6.92 (d, J = 7.8 Hz, 1H, ArH) 7.45 (d, J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 7.5 Hz, 1H, ArH) 7.76 (t, J = 7.5 Hz, 1H, ArH) 7.86 (d, J = 7, 8 Hz, 1H, ArH) 7.94 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 118> 9b-Acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylmethylcarbamate

Methylisocyanate (0.12 g, 2.22 mmol) and trimethylamine (0.18 g, 1.77 mmol) were added to a solution of 9b-chloro-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.50 g, 1.48 mmol) in anhydrous THF (15 ml) and heated for 5 hours at the boil under reflux. After THF was removed by concentration in vacuo, the residue was diluted in methylene chloride and washed many times with water. The organic layer was dried, filtered and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.10 g (17%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (dd, J = 2.4, 6.9 Hz, 6H, CH ₃ ) 1.96 (s, 3H, CH ₃ ) 2.77-2 88 (m, 4H, CH, CH ₃ ) 5.14 (s, 1H, NH) 6.26 (s, 1H, NH) 6.70 (s, 1H, ArH) 6.90 (d, J = 7.8 Hz, 1H, ArH) 7.45 (d, J = 7.8 Hz, 1H, ArH) 7.56 (t, J = 6.9 Hz, 1H, ArH) 7.75 (t, J = 6.9 Hz, 1H, ArH) 7.83-7.90 (m, 2H, ArH).

<EXAMPLE 119> N, N ′ - (7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) diacetamide

4b, 9b-Diazido-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (2.50 g, 7.2 mmol) was dissolved in 50 ml of EtOH and stirred overnight in the presence of 10% Pd / C (0.38 g) in a hydrogen atmosphere.

The reaction mixture was filtered through a celite pad and concentrated in vacuo to give 4b, 9b-diamino-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (1.60 g, 5.4 mmol). This compound was dissolved in 50 ml THF and Et ₃ N (3.02 ml, 21.7 mmol) and acetyl chloride (1.16 ml, 16.3 mmol) was added to the solution and stirred overnight at room temperature. After concentration in vacuo, the residue was purified by column chromatography (ethyl acetate: hexane = 2: 1) to obtain the title compound. 0.28 g (10%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.14 (d, J = 3.1 Hz, 3H), 1.16 (d, J = 3.1 Hz, 3H), 1.83 (s, 3H), 1.87 (s, 3H), 2.80 (q, J = 7.6 Hz, 1H), 6.62-6.68 (m, 2H), 6.83 (d, J = 7.8 Hz, 1H), 7.05 (s, 1H), 7.36 (d, J = 7.8 Hz, 1H), 7.54 (t, J = 8.7 Hz, 1H), 7 72 (t, J = 8.7 Hz, 1H); 7.82 (t, J = 9.5 Hz, 1H).

<EXAMPLE 120> 4b- (Benzyloxy) -9b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

p-Toluene sulfuric acid (65 mg, 0.33 mmol) was added to a solution of 4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one ( 0.50 g, 1.68 mmol) in benzyl alcohol (5 ml) and stirred at 60 ° C for 3 days. The reaction mixture was concentrated and purified by silica gel column chromatography (30% ethyl acetate mixed with 10% hexane) to obtain the title compound. 20 mg (3%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (dd, J = 3 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.86 (sept., J = 6.9 Hz, 1H , CH) 3.42 (br, 1H, OH) 5.03 (d, J = 11.4 Hz, 1H, CH ₂ ) 5.12 (d, J = 11.4 Hz, 1H, CH ₂ ) 6.76 (s, 1H, ArH) 6.90 (d, J = 7.8 Hz, 1H, ArH) 7.29-7.37 (m, 3H, ArH) 7.42-7.47 (m , 3H, ArH) 7.54-7.59 (m, 1H, ArH) 7.77-7.82 (m, 2H, ArH) 7.98 (d, J = 7.8 Hz, 1H, ArH) .

<EXAMPLE 121> 9b-Acetylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of phenyl carbonic ester

Phenylchloroformate (0.35 g, 2.22 mmol) and trimethylamine (0.18 g, 1.77 mmol) were added to a solution of N- (4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5 -oxaindeno [2,1-a] inden-9b-yl) acetamide (0.50 g, 1.48 mmol) in anhydrous THF and heated for 24 hours at the boil under reflux. After THF was removed by concentration in vacuo, the residue was diluted in ethyl acetate and washed several times with aqueous sodium bicarbonate. The organic layer was dried, filtered and purified by column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound. 10 mg (1.5%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (dd, J = 3.9, 6.9 Hz, 6H, CH ₃ ) 2.04 (s, 3H, CH ₃ ) 2.78-2 87 (m, 1H, CH) 6.13 (s, 1H, NH) 6.71 (s, 1H, ArH) 6.90 (d, J = 7.8 Hz, 1H, ArH) 7.16 ( d, J = 7.8 Hz, 2H, ArH) 7.36-7.46 (m, 4H, ArH) 7.61 (t, J = 7.8 Hz, 1H, ArH) 7.81 (t, J = 7.5 Hz, 1H, ArH) 7.88 (d, J = 7.5 Hz, 1H, ArH) 8.07 (d, J = 9.0 Hz, 1H, ArH).

<EXAMPLE 122> O- (9b-Azido-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) phenylthiocarbamic acid ester

Phenyl isothiocyanate (0.62 g, 4.66 mmol) and trimethylamine (0.37 g, 3.73 mmol) were added to the solution of 9b-azido-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [ 2,1-a] inden-10-one (1.00 g, 3.11 mmol) in anhydrous THF and heated for 24 hours at the boil under reflux. After THF was removed by vacuum concentration, the residue was diluted in ethyl acetate and washed many times with aqueous sodium bicarbonate. The organic layer was dried, filtered and purified by column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.15 g (10%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.23 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.86-2.95 (sept., 1H, CH) 6.84 (s , 1H, NH) 6.95-7.05 (m, 3H, ArH) 7.29 (d, J = 7.5 Hz, 1H, ArH) 7.36 (d, J = 8.1 Hz, 2H , ArH) 7.46-7.61 (m, 3H, ArH) 7.71 (t, J = 7.5 Hz, 1H, ArH) 7.91 (d, J = 7.8 Hz, 1H, ArH )

<EXAMPLE 123> Ethyl-9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate

Iron powder (0.45 g, 8.0 mmol) and conc. HCl (0.03 ml) was added to a solution of ethyl 9b-acetamido-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 4b-ylcarbonate (0.50 g, 1.1 mmol) in ethanol (10 ml) and water (1 ml) and heated for 1 hour at the boil under reflux. The reaction mixture was washed with MeOH, filtered and concentrated in vacuo. Purified through column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 0.32 g (69%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16-1.19 (m, 9H, CH ₃ ) 2.17 (s, 3H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 4.05-4.15 (m, 2H, OCH ₂ ) 4.44 (s, 3H, NCH ₂ ) 5.33 (s, 1H, NH) 6.72 (s, 1H, ArH) 6, 90 (d, J = 7.8 Hz, 1H, ArH) 6.96 (d, J = 7.8 Hz, 1H, ArH) 7.23-7.25 (m, 1H, ArH) 7.32 ( t, J = 7.8 Hz, 1H, ArH) 7.41 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 124> N, N ′ - (7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) dipropionamide

To 4b, 9b-diamino-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.50 g, 1.70 mmol) was added 10 ml of THF. This solution was stirred at room temperature overnight with Et ₃ N (0.94 ml, 6.79 mmol) and propinol chloride (0.44 ml, 5.09 mmol). After concentration in vacuo, purification by column chromatography (ethyl acetate: hexane = 2: 1) gave the title compound (0.27 g, 39%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.05-1.17 (m, 12H), 2.08-2.39 (m, 4H), 2.82 (q, J = 7.6 Hz, 1H), 6.27 (s, 1H), 6.51 (s, 1H), 6.67 (s, 1H), 6.85 (d, J = 7.8 Hz, 1H), 7, 39 (d, J = 8.4 Hz, 1H), 7.56 (t, 8.4 Hz, 1H), 7.75 (t, 8.4 Hz, 1H), 7.85 ( d, J = 7.8 Hz, 2H).

<EXAMPLE 125> N, N ′ - (7-Isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) bis (2-methylpropanamide)

To 4b, 9b-diamino-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.50 g, 1.70 mmol) was added 10 ml of THF. This solution was stirred overnight with Et ₃ N (0.94 ml, 6.79 mmol) and isobutyryl chloride (0.53 ml, 5.09 mmol) at room temperature. After vacuum concentration, purification by column chromatography (ethyl acetate: hexane = 1: 1) gave the title compound. 0.27 g (39%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.05-1.20 (m, 18H), 2.35-2.46 (m, 2H), 2.80 (q, J = 6.9 Hz, 1H), 6.43 (s, 1H), 6.65 (s, 1H), 6.78 (s, 1H), 6.83 (d, J = 7.5 Hz, 1H), 7, 36 (d, J = 8.0 Hz, 1H), 7.52 (t, J = 8.0 Hz, 1H), 7.71 (t, J = 8.5 Hz, 1H), 7.82 ( t, J = 8.5 Hz, 2H).

<EXAMPLE 126> 4b, 9b-Dihydroxy-7-isopropyl-4bH-benzofuro [2 ′, 3 ′: 3,4] cyclopenta [1,2-b] pyridin-10 (9bH) -one

To 5H-cyclopenta [b] pyridin-7 (6H) -one (1.50 g, 11.26 mmol) was added 10 ml of dioxane and 1 ml of AcOH. The solution was stirred overnight with SeO ₂ (3.75 g, 33.79 mmol) in a reflux apparatus. Neutralization with a NaHCO ₃ solution was followed by extraction with ethyl acetate. The extract was concentrated in vacuo to give 6,6-dihydroxy-5H-cyclopenta [b] pyridin-5,7 (6H) -dione (1.50 g, 8.37 mmol). The concentrate was dissolved in 10 ml AcOH and stirred overnight with isopropylphenol (1.14 g, 8.37 mmol) in a reflux apparatus. Concentration in vacuo and purification by column chromatography (ethyl acetate: hexane = 2: 1) gave the title compound (0.70 g, 21%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (d, J = 4.1 Hz, 3H), 1.19 (d, J = 4.1 Hz, 3H), 2.85 (q. , J = 7.2 Hz, 1H), 3.77 (s, 1H), 6.74 (s, 1H), 6.94 (d, J = 7.5 Hz, 1H), 7.27 (d , J = 5.2 Hz, 1H), 7.58 (d, J = 7.5 Hz, 1H), 7.65 (s, 1H), 8.07 (d, J = 7.9 Hz, 1H )

<EXAMPLE 127> 10-Hydroxy-7-isopropyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl diacetate

Solution of 7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl diacetate (0.10 g, 0.26 mmol) in absolute MeOH (5 ml) stirred with sodium borohydride (20 mg, 0.53 mmol) at room temperature for 7 hours. Acetone (5 ml) was added and the reaction mixture was stirred for 10 minutes until the reaction stopped. Then the solvent was removed. The reaction mixture was extracted with DCM and water, dried, concentrated in vacuo and purified by silica gel column chromatography (30% ethyl acetate mixed with 20% hexane) to obtain the title compound. 30 mg (30%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (dd, J = 3.6 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.10 (s, 3H, OAc) 2.16 (s, 3H, OAc) 2.81 (sept., J = 6.9 Hz, 1H, CH) 4.38 (d, J = 3 Hz, 1H, OH) 5.93 (d, J = 3 Hz , 1H, CH) 6.72 (s, 1H, ArH) 6.81 (d, J = 8.1 Hz, 1H, ArH) 7.36-7.50 (m, 3H, ArH) 7.57 ( d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 128> O-Methyloxime 9b-hydroxy-7-isopropyl-4b- (methoxyamino) -4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

O-methylhydroxylamine hydrochloride (564 mg, 6.75 mmol) was added to a solution of 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (1.00 g, 3.37 mmol) in aqueous pyridine (10 ml) and stirred at room temperature. After 3 hours, the solvent was removed and the reaction mixture was washed with DCM and 1N. HCl. The organic layer was washed again with water and brine, concentrated in vacuo, and separated by silica gel column chromatography (30% ethyl acetate mixed with 10% hexane) to obtain the title compound. 100 mg (9%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.81 (sept., J = 6.9 Hz 1H, CH) 3.98 (s, 3H, N-OCH ₃ ) 4.09 (s, 3H, N-OCH ₃ ), 4.46 (s, 1H, OH) 6.57 (dd, J = 1.8 Hz, J = 8 , 1 Hz, 1H, ArH) 6.82 (d, J = 8.1 Hz, 1H, ArH) 6.88 (d, J = 1.5 Hz, 1H, ArH) 7.44-7.55 ( m, 2H, ArH) 7.87 (dd, J = 1.2 Hz, 6.9 Hz, 1H, ArH) 8.20 (dd, J = 1.2 Hz, J = 6.9 Hz, 1H, ArH) 8.73 (s, 1H, NH).

<EXAMPLE 129> 7-Isopropyl-4b-methoxy-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-ol

A solution of 1 M tertiary potassium butoxide (1.25 ml, 1.25 mmol) in THF was slowly added at 0 ° C to a solution of methyltriphenylphosphonium bromide (415 mg, 1.16 mmol) in anhydrous THF (5 ml) and stirred at 0 ° C for 30 minutes and then at room temperature for 3 hours. A solution of 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.30 g, 0.97 mmol) was slowly added to this mixture. ) in anhydrous THF (5 ml) at 0 ° C and heated for 24 hours at the boil under reflux. The reaction mixture was concentrated in vacuo and washed with water (50 ml) and DCM (50 ml × 2). The organic layer was washed again with water (30 ml) and brine (30 ml), dried over sodium sulfate, filtered and concentrated in vacuo. Purification by column chromatography (30% ethyl acetate mixed with 10% hexane) gave the title compound. 30 mg (10%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 3 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.81 (sept., J = 6.9 Hz, 1H , CH) 2.97 (br, 1H, OH) 3.67 (s, 3H, OMe) 5.71 (d, J = 9.9 Hz, 2H, olefinic CH ₂ ) 6.69 (s, 1H , ArH) 6.80 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.35-7.40 (m, 3H, ArH) 7.46-7.51 (m , 1H, ArH) 7.66-7.68 (m, 1H, ArH).

<EXAMPLE 130> O-Methyloxime 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

O-methyl hydroxylamine hydrochloride (269 mg, 3.20 mmol) was added to a solution of 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (0, 50 g, 1.61 mmol) in anhydrous pyridine (10 ml) and stirred overnight at room temperature. After removing the solvent, the residue was washed with DCM and 1N. HCl. The organic layer was washed again with water and brine, concentrated in vacuo, and purified by silica gel column chromatography (30% ethyl acetate mixed with 20% hexane) to obtain the title compound. 60 mg (11%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (dd, J = 2.4 Hz, J = 6.9 Hz, 6H, CH ₃ ) 1.40 (s, 3H, CH ₃ ), 1 46 (s, 3H, CH ₃ ), 2.87 (sept., 1H, CH) 6.76 (d, J = 0.9 Hz, 1H, ArH) 6.92 (dd, J = 1.2 Hz, J = 7.8 Hz, 1H, ArH) 7.55-7.60 (m, 2H, ArH) 7.77-7.82 (m, 2H, ArH) 7.90 (m, 1H, ArH )

<EXAMPLE 131> A mixture of 1-bromo and 4-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

To a solution of 4-bromo-1-indanone (10.0 g, 47.4 mmol) in AcOH (4.0 ml) and dioxane (40 ml) was added SeO ₂ (11.5 g, 104 mmol), followed by heating in for 4 hours at the boil under reflux. The reaction mixture was filtered and concentrated to give a dark brown oil. m-Isopropylphenol (6.81 g, 50.0 mmol) and AcOH (10 ml) were added to the dark brown oil and stirred overnight. The reaction mixture was purified by column chromatography (EtOAc / Hexane = 1 / 4-1 / 2 eluted) to give the title compound as a brown solid. 9.28 g (52%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (d, J = 6.9 Hz, 6H), 2.84 (hept., J = 6.9 Hz, 1H), 4.07 (s , br., 1H), 4.81 (s, br., 1H), 6.71 (s, 0.34H), 6.79 (d, J = 1.2 Hz, 0.66H), 6, 85 (dd, J = 7.9, 1.2 Hz, 1H), 7.37-7.42 (m, 1.64H), 7.57-7.62 (m, 0.36H), 7, 67-7.75 (m, 1H); 7.91-7.97 (m, 1H).

<EXAMPLE 132> 1- (Benzylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

Benzaldehyde (0.30 g, 2.88 mmol) and NaCNBH ₃ (0.12 g, 1.92 mmol) were added at 0 ° C to a solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-4b, 9b -dihydro-5-oxaindeno [2,1-a] inden-10-one (0.30 g, 0.96 mmol) in absolute MeOH (3 ml), followed by reaction overnight at room temperature. The solvent was removed by concentration in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 80 mg (15%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.79-2.88 (m, 1H, CH) 4.50 (d, J = 6.0 Hz, 2H, CH ₂ ) 6.57 (d, J = 8.1 Hz, 1H, ArH) 6.73 (s, 1H, ArH) 6.83 (d, J = 7.8 Hz, 1H, ArH) 7.11 (d, J = 7.2 Hz, 1H, ArH) 7.31-7.39 (m, 5H, ArH) 7.47-7.53 (m, 2H, ArH )

<EXAMPLE 133> 1- (Ethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

Acetaldehyde (0.08 g, 1.92 mmol) and NaCNBH ₃ (0.08 g, 1.28 mmol) were added at 0 ° C to a solution of 1-amino-4b, 9b-dihydroxy-7-isopropyl-4b, 9b -dihydro-5-oxaindeno [2,1-a] inden-10-one (0.20 g, 0.64 mmol) in absolute MeOH (3 ml) and the reaction was carried out at room temperature for 2 days. After removing the solvent by concentration in vacuo, column chromatography (ethyl acetate: hexane = 1: 2) was performed to obtain the title compound. 40 mg (18%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.6 Hz, 6H, CH ₃ ) 1.26 (t, J = 6.9 Hz, 3H, CH ₃ ) 2, 77-2.88 (m, 1H, CH) 3.16-3.25 (m, 2H, CH ₂ ) 6.57 (d, J = 8.1 Hz, 1H, ArH) 6.65 (s, 1H, NH) 6.80 (d, J = 7.5 Hz, 1H, ArH) 6.94 (s, 1H, ArH) 7.07 (d, J = 7.2 Hz, 1H, ArH) 7, 39 (d, J = 7.2 Hz, 1H, ArH) 7.54 (t, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 134> 9b-Hydroxy-7-isopropyl-4b-methyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one

7-Isopropyl-4b-methoxy-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-ol (50 mg, 0.16 mmol) was dissolved in THF: conc. HCl (1: 1, 1 ml) and heated under reflux for 30 minutes. After removing the solvent, the residue was washed with DCM (50 ml) and water (20 ml). The organic layer was washed again with water and brine, concentrated in vacuo. The concentrate was purified by silica gel column chromatography (30% ethyl acetate mixed with 15% hexane) to obtain the title compound. 20 mg (40%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 2.7 Hz, J = 6.9 Hz, 6H, CH ₃ ) 1.79 (s, 3H, CH ₃ ) 2, 82 (sept., J = 6.9 Hz, 1H, CH) 3.29 (s, 1H, OH) 6.67 (d, J = 1 Hz, 1H, ArH) 6.80 (dd, J = 1 Hz, J = 7.8 Hz, 1H, ArH) 7.35 (d, J = 7.8 Hz, 1H, ArH) 7.50 (t, J = 7.8 Hz, 1H, ArH) 7.72 -7.78 (m, 2H, ArH); 7.83 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 135> 4b, 9b-Dihydroxy-5-isobutyryl-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indole-10 (9bH) -one

Conc. HCl (5 ml) was added to a solution of N- (2- (2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl) -4,5-dimethylphenyl) isobutyramide (200 mg, 0.57 mmol) in THF (5 ml) and stirred for 8 hours. To stop the reaction, excess water (50 ml) was added, and then extraction was performed with ethyl acetate and water. The organic layer was washed with brine, concentrated, and purified by silica gel column chromatography (30% ethyl acetate mixed with 20% hexane) to obtain the title compound. 120 mg (6%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 6.9 Hz, 3H, CH ₃ ) 1.25 (d, J = 6.9 Hz, 3H, CH ₃ ) 2, 16 (s, 3H, CH ₃ ) 2.17 (s, 3H, CH ₃ ) 2.74 (sept., J = 6.9 Hz, 1H, CH) 3.91 (s, 1H, OH) 4, 90 (s, 1H, OH) 6.48 (s, 1H, ArH) 7.30 (s, 1H, ArH) 7.46-7.54 (m, 1H, ArH) 7.72-7.83 ( m, 3H, ArH).

<EXAMPLE 136> 7-Isopropyl-10-methyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diol

7-Isopropyl-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diol (50 mg, 0.20 mmol) was dissolved in absolute MeOH (5 ml) and stirred within 24 hours in the presence of Pd / C (10%, 10 mg) in a hydrogen atmosphere. The reaction mixture was washed with DCM, filtered through a filter with celite and concentrated. Purification by silica gel column chromatography (30% ethyl acetate mixed with 20% hexane) gave the title compound. 30 mg (60%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.13-1.19 (m, 6H + 3H, CH ₃ ) 2.73-2.83 (sept., J = 6.9 Hz, 1H, CH ) 3.66-3.74 (m, 1H, CH) 3.82 (s, 1H, OH) 6.34 (d, J = 8.1 Hz, 0.8H, ArH) 6.52 (dd, J = 1.5 Hz, J = 8.1 Hz, 0.8H, ArH) 6.78 (d, J = 1.5 Hz, 0.8H, ArH) 7.46-7.51 (m, 1 6H, ArH) 7.70-7.75 (m, 0.8H, ArH) 8.50 (s, 1H, ArH).

<EXAMPLE 137> N- (1-Bromo-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide

Oxalyl chloride (0.60 ml, 6.88 mmol) and DMF (3 drops) were added to the solution of 1-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH ) -one (1.98 g, 5.28 mmol) in DCM (20 ml) and stirred at room temperature for 3 hours. The reaction was stopped by adding water, followed by extraction with DCM and water. The organic layer was dried and concentrated in vacuo to give 1-bromo-9b-chloro-4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one as a solid. 1.81 g

To a solution of 1-bromo-9b-chloro-4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (1.81 g) in THF (15 ml) was added 2 , 0 M NH ₃ in i-PrOH (8.0 ml, 16 mmol) at 0 ° C. After 30 minutes, the temperature was raised to room temperature, and the solution was stirred for 1 hour. The reaction was stopped by adding water, followed by extraction with ethyl acetate and water. The organic layer was dried and concentrated in vacuo to give 1.57 g of 9b-amino-1-bromo-4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one as dark brown solid.

This compound (1.55 g) was dissolved in acetic acid (5 ml) and heated for 30 minutes under reflux in the presence of Ac ₂ O (390 mg, 3.82 mmol). The reaction mixture was extracted with ethyl acetate and water, and the organic layer was concentrated in vacuo and purified by column chromatography (EtOAc / Hexane = 1 / 1-1 / 1 eluted) to give the title compound as a yellow solid. 510 mg (23%).

¹ H-NMR (500 MHz, CDCl ₃ ) (major: minor = 58: 42 regioisomeric mixture) δ 1.16-1.18 (m, 6H), 2.06 (s, 1.7H major), 2, 08 (s, 1.3H minor), 2.81-2.85 (m, 1H), 6.44 (s, br., 0.58H), 6.70 (d, br., J = 1, 4 Hz, 0.84H), 6.78 (d, J = 1.4 Hz, 0.58H), 6.83-6.86 (m, 1H), 7.25 (d, J = 8.1 Hz, 0.42H), 7.29 (d, J = 7.9 Hz, 0.58H), 7.40 (t, J = 7.7 Hz, 0.58H), 7.61 (t, J = 7.7 Hz, 0.42H), 7.69 (dd, J = 7.8, 0.9 Hz, 0.42H), 7.75 (dd, J = 7.6, 0.8 Hz, 0.58H), 7.91 (dd, J = 7.8, 1.0 Hz, 0.58H), 7.95 (dd, J = 7.7, 0.9 Hz, 0.48H).

<EXAMPLE 138> 4b, 9b-Dihydroxy-5-isobutyryl-7,8-dimethoxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one

Conc. HCl (5 ml) was added to a solution of N- [2- (2-hydroxy-1,3-dioxo-indan-2-yl) -4,5-dimethoxyphenyl] isobutyramide (500 mg, 1.30 mmol) in anhydrous THF (5 ml) and stirred at room temperature for 3 hours. The reaction mixture was washed repeatedly with ethyl acetate and water, and the organic layer was dried, filtered and concentrated in vacuo, followed by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 100 mg (20%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.19-1.37 (m, 6H, CH ₃ ) 2.70-2.80 (m, 1H, CH), 3.10 (s, 1H, CH) 3.78 (s, 3H, OMe) 3.84 (s, 3H, OMe) 4.87 (s, 1H, OH) 6.25 (s, 1H, ArH), 6.97 (s, 1H , ArH) 7.51 (t, J = 7.2 Hz, 1H, ArH) 7.73-7.82 (m, 3H, ArH).

<EXAMPLE 139> 4b, 9b-Dihydroxy-7-isopropyl-2-piperidinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Piperidine (136 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to the solution of 4b, 9b-dihydroxy-7-isopropyl-2-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (2 ml) and the reaction was carried out at 110 ° C for 10 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (50 mg, 8%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H), 1.68 (s, 8H), 2.82 (sept., J = 6.9H , 1H), 3.49 (s, 4H), 6.66 (s, 1H), 6.81 (d, J = 7.6 Hz, 1H), 7.07 (d, J = 9 Hz, 1H ), 7.22 (d, J = 1.2 Hz, 1H), 7.41 (d, J = 7.7 Hz, 1H), 7.55 (d, J = 8.6 Hz, 1H).

<EXAMPLE 140> 4b, 9b-Dihydroxy-7-isopropyl-2-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Morpholine (140 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to the solution of 4b, 9b-dihydroxy-7-isopropyl-2-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (2 ml) and the reaction was carried out at 110 ° C for 10 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (60 mg, 10%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.15 (t, J = 5.8 Hz, 6H), 2.80 (sept., J = 6.9H, 1H), 3.32 (t , J = 1.5 Hz, 4H), 3.76 (t, J = 4.5 Hz, 4H), 6.68 (s, 1H), 6.81 (d, J = 7.6 Hz, 1H ), 7.06 (d, J = 8.3 Hz, 1H), 7.24 (s, 1H), 7.41 (d, J = 7.8 Hz, 1H), 7.57 (d, J = 8.8 Hz, 1H).

<EXAMPLE 141> 4b, 9b-Dihydroxy-7-isopropyl-1-piperidinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Piperidine (140 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-1-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 10 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a fluorescent yellow solid (110 mg, 18%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.16 (dd, J = 6.9 Hz, 4.9 Hz, 6H), 1.59 (quint, J = 5.8 Hz, 2H), 1.74 (m, 4H), 2.81 (sept., J = 6.9H, 1H), 3.02 (m, 2H), 3.09 (m, 2H), 6.64 (s, 1H ), 6.81 (d, J = 7.8 Hz, 1H), 6.93 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 7.5 Hz, 1H), 7.38 (d, J = 7.8 Hz, 1H); 7.61 (t, J = 7.8 Hz, 1H).

<EXAMPLE 142> 4b, 9b-Dihydroxy-7-isopropyl-1-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Morpholine (140 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to the solution of 4b, 9b-dihydroxy-7-isopropyl-1-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 10 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a fluorescent yellow solid (80 mg, 13%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.14 (t, J = 6.25 Hz, 6H), 2.79 (sept., J = 6.8 Hz, 1H), 3.00 ( m, 2H), 3.11 (m, 2H), 3.83 (s, 4H), 6.67 (s, 1H), 6.81 (d, J = 8.0 Hz, 1H), 6, 84 (d, J = 8.2 Hz, 1H), 7.40 (d, J = 7.8 Hz, 1H), 7.44 (d, J = 7.5 Hz, 1H), 7.61 ( t, J = 7.8 Hz, 1H).

<EXAMPLE 143> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) propionamide

Trimethylacetic anhydride (0.27 g, 1.46 mmol) was added to a solution of 9b-chloro-4b-hydroxy-5.9b-dihydro-4bH-indeno [1,2-b] indol-10-one (0.50 g , 1.46 mmol) in pivalic acid (5 ml) and heated at 100 ° C for 30 minutes. The reaction mixture was diluted in ethyl acetate and washed repeatedly with aq. NaHCO ₃ . The organic layer was dried, filtered, concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 50 mg (14%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.07 (t, J = 7.5 Hz, 3H, CH ₃ ) 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 2, 24-2.32 (m, 2H, CH ₂ ) 2.77-2.86 (m, 1H, CH) 6.64-6.65 (m, 2H, ArH) 6.82 (d, J = 6 6 Hz, 1H, ArH) 6.98 (d, J = 7.2 Hz, 1H, ArH) 7.33 (m, 1H, ArH) 7.38-7.43 (m, 1H, ArH).

<EXAMPLE 144> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) butyramide

H ₂ O (0.5 ml), Fe (0.28 g, 5.14 mmol) and conc. HCl (0.03 mmol) was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl ) butyramide (0.30 g, 0.70 mmol) in EtOH (5 ml) and heated for 1 hour at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered. The filtrate was then concentrated and purified by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 0.20 g (75%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 0.95 (t, J = 7.5 Hz, 3H, CH ₃ ) 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 1 56-1.63 (m, 1H, CH ₂ ) 2.23 (t, J = 7.5 Hz, 2H, CH ₂ ) 2.79-2.83 (m, 1H, CH) 6.64 ( s, 2H, ArH) 6.82 (d, J = 7.8 Hz, 1H, ArH) 6.98 (d, J = 6.6 Hz, 1H, ArH) 7.33 (s, 1H, ArH) 7.40 (t, J = 6.6 Hz, 1H, ArH).

<EXAMPLE 145> 4b, 9b-Dihydroxy-5-isobutyryl-7-isopropyl-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one

Conc. HCl (2 ml) was added to a solution of N- [2- (2-hydroxy-1,3-dioxoindan-2-yl) -5-isopropylphenyl] isobutyramide (80 mg, 0.21 mmol) in anhydrous THF (2 ml) and stirred at room temperature for 3 hours. The reaction mixture was washed repeatedly with ethyl acetate and water, the organic layer was dried, filtered and concentrated in vacuo, followed by purification by column chromatography (ethyl acetate: hexane = 1: 4) to obtain the title compound. 33 mg (41%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15-1.25 (m, 12H, CH ₃ ) 2.68-2.84 (m, 2H, CH) 3.08 (s, 1H, OH ) 5.02 (s, 1H, OH) 6.51 (s, 1H, ArH) 6.76 (d, J = 8.1 Hz, 1H, ArH) 7.44 (d, J = 8.1 Hz , 1H, ArH) 7.51 (t, J = 7.5 Hz, 1H, ArH) 7.73-7.84 (m, 3H, ArH).

<EXAMPLE 146> 4b, 9b-Dihydroxy-7-isopropyl-2- (hydroxypiperidinyl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Hydroxypiperidine (162 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-2-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 5 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (65 mg, 10%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (dd, J = 6.9 Hz, 1.4 Hz, 6H), 1.57 (m, 2H), 1.95 (m, 2H ), 2.80 (sept., J = 6.9 Hz, 1H), 3.24 (m, 2H), 3.92 (m, 3H), 6.63 (s, 1H), 6.80 ( d, J = 7.7 Hz, 1H), 7.12 (d, J = 7.7 Hz, 1H), 7.25 (s, 1H), 7.39 (d, J = 7.6 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H).

<EXAMPLE 147> 4b, 9b-Dihydroxy-1- (4-hydroxypiperidin-1-yl) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Hydroxypiperidine (162 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-1-fluoro-4bH-benzo [d] indeno [1,2- b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 5 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a fluorescent yellow solid (60 mg, 10%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.6 Hz, 6H), 1.74 (m, 2H), 1.94 (s, 2H), 2.79 (m, 3H), 3.44 (s, 1H), 3.76 (m, 1H), 6.63 (s, 1H), 6.81 (d, J = 7.9 Hz, 1H), 6 98 (d, J = 7.9 Hz, 1H), 7.36 (d, J = 7.5 Hz, 2H), 7.63 (t, J = 7.4 Hz, 1H).

<EXAMPLE 148> 4b, 9b-Dihydroxy-7-isopropyl-2- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH )-it

1- (4-Methoxybenzyl) piperazine (136 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to the solution of 4b, 9b-dihydroxy-7-isopropyl-2-fluoro-4bH-benzo [d ] indeno [1,2-b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 5 minutes using a microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (70 mg, 9%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, 6.8 Hz), 2.60 (s, 4H), 2.80 (sept., J = 6.8 Hz, 1H) 3.47 (s, 4H), 3.55 (s, 2H), 3.80 (s, 3H), 6.74 (s, 1H), 6.78 (br, 1H), 6.87 (d, J = 7.8 Hz, 2H), 6.93 (s, 1H), 7.23 (m, 3H), 7.40 (br, 1H), 7.60 (br, 1H) .

<EXAMPLE 149> 4b, 9b-Dihydroxy-7-isopropyl-1- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH )-it

1- (4-Methoxybenzyl) piperazine (140 mg, 1.60 mmol) and triethylamine (200 mg, 1.98 mmol) were added to the solution of 4b, 9b-dihydroxy-7-isopropyl-1-fluoro-4bH-benzo [d ] indeno [1,2-b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 5 minutes using a microwave radiation. The product was purified by column chromatography to give the title compound as a fluorescent yellow solid (84 mg, 11%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H), 2.65 (m, 4H), 2.81 (sept., J = 6.9 Hz, 1H), 3.18 (t, J = 4.6 Hz, 4H), 3.53 (d, 2.6 Hz, 2H), 3.80 (s, 3H), 6.70 (s, 1H), 6.79 (d, J = 7.8 Hz, 1H), 6.89 (m, 3H), 7.43 (d, J = 7.4 Hz, 1H), 7.62 (t, J = 7.8 Hz).

<EXAMPLE 150> 2- (Dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Dimethylamine hydrochloride (136 mg, 1.60 mmol) and triethylamine (400 mg, 3.96 mmol) were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-2-fluoro-4bH-benzo [d] indeno [1,2 -b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 5 minutes using microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (73 mg, 10%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H), 2.82 (sept., J = 6.9 Hz, 1H), 3.14 ( s, 6H), 6.71 (s, 1H), 6.80 (t, J = 7.5 Hz, 2H), 7.05 (d, J = 7.8 Hz, 1H), 7.43 ( d, J = 7.8 Hz, 1H); 7.62 (d, J = 8.8 Hz, 1H).

<EXAMPLE 151> 1- (Dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

Dimethylamine hydrochloride (140 mg, 1.60 mmol) and triethylamine (400 mg, 3.96 mmol) were added to a solution of 4b, 9b-dihydroxy-7-isopropyl-1-fluoro-4bH-benzo [d] indeno [1,2 -b] furan-10 (9bH) -one (250 mg, 0.80 mmol) in N, N-dimethylformamide (1 ml) and the reaction was carried out at 110 ° C for 10 min using microwave radiation. The product was purified by column chromatography to give the title compound as a yellow solid (168 mg, 31%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (dd, J = 6.9, 2.8 Hz, 6H), 2.82 (sept., J = 6.9 Hz, 1H), 2.95 (s, 6H), 6.71 (d, J = 1.25 Hz, 1H), 6.80 (m, 2H), 7.30 (t, J = 7.9 Hz, 2H), 7.57 (t, J = 7.4 Hz, 1H).

<EXAMPLE 152> 10-Hydrazono-7-isopropyl-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diol

4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 mg, 1.69 mmol) and hydrazine monohydrate (125 mg, 2, 50 mmol) was dissolved in toluene (5 ml) in a reactor and stirred overnight at room temperature. The product was purified by column chromatography to give the title compound as a white solid. 7 mg, (1%).

¹ H-NMR (300 MHz, DMSO) δ 1.15 (d, J = 6.9 Hz, 6H), 2.80 (sept., J = 6.8 Hz, 1H), 5.83 (br. , 1H), 6.72 ~ 6.76 (m, 2H), 7.48 (t, J = 7.8 Hz, 1H), 7.64 ~ 7.70 (m, 2H), 7.75 ( d, J = 7.9 Hz, 1H), 7.83 (d, J = 7.7 Hz, 1H), 11.24 (s, 1H).

<EXAMPLE 153> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide

Iron powder (38 mg, 0.68 mmol) was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran -9b-yl) benzamide (0.10 g, 0.23 mmol) in ethanol: water (10: 1, 10 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 80 mg (86%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz, 1H, CH) 6 67 (br, 2H, ArH) 6.87-6.89 (m, 1H, ArH) 7.01-7.03 (m, 1H, ArH) 7.40-7.54 (m, 5H, ArH) 7.83-7.86 (m, 2H, ArH).

<EXAMPLE 154> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxybenzamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxybenzamide (0.10 g , 0.21 mmol) was dissolved in ethanol: water (10: 1, 10 ml) and heated for 3 hours in the presence of iron powder (36 mg, 0.63 mmol) under reflux. The reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 85 mg (90%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz, 1H, CH) 3 82 (s, 3H, OCH ₃ ) 6.67-6.72 (m, 2H, ArH) 6.89 (d, J = 6.3 Hz, 1H, ArH) 7.03-7.09 (m , 2H, ArH) 7.31-7.36 (m, 1H, ArH) 7.43-7.49 (m, 4H, ArH).

<EXAMPLE 155> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chlorobenzamide

4-Chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide (0.08 g, 0.17 mmol) was dissolved in ethanol: water (10: 1, 10 ml) and heated for 3 hours in the presence of iron powder (28 mg, 0.50 mmol) under reflux. The reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 60 mg (80%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz, 1H, CH) 6 66-6.75 (m, 2H, ArH) 6.88 (d, J = 7.8 Hz, 1H, ArH) 7.01 (d, J = 7.5 Hz, 1H, ArH) 7.41 -7.46 (m, 4H, ArH) 8.83 (d, J = 8.4 Hz, 2H, ArH).

<EXAMPLE 156> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-nitrobenzamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-nitrobenzamide (0.075 g, 0 , 15 mmol) was dissolved in ethanol: water (10: 1, 10 ml) and heated for 6 hours in the presence of iron powder (52 mg, 0.92 mmol) under reflux. The reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 50 mg (76%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 6 60-6.69 (m, 4H, ArH) 6.86-6.88 (m, 1H, ArH) 6.99-7.01 (m, 1H, ArH) 7.40-7.46 (m , 2H, ArH) 7.60-7.63 (m, 2H, ArH).

<EXAMPLE 157> 1-amino-4b, 9b-dihydroxy-6,8-diisopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one

4b, 9b-dihydroxy-6,8-diisopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (300 mg, 0.78 mmol) was dissolved in ethanol : water (10 ml: 1 ml). To this solution was added Fe (319 mg, 5.7 mmol) and one drop conc. HCl, followed by heating for 1 hour at the boil under reflux. After neutralization with a NaHCO ₃ solution, concentration in vacuo and purification by column chromatography (20% methanol in methylene chloride) gave the title compound (90 mg, 33%).

¹ H-NMR (300 MHz, DMSO) δ 1.09 ~ 1.17 (m, 12H), 2.81 (sept., J = 6.8 Hz, 1H), 2.93 (sept., J = 6.8 Hz, 1H), 6.36 (s, 1H), 6.64-6.68 (m, 2H), 6.97 (s, 1H), 7.08 (d, J = 1.2 Hz, 1H), 7.43 (t, J = 7.7 Hz, 1H), 7.50 (s, 1H).

<EXAMPLE 158> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) cyclopropanecarboxamide

Solution N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) cyclopropanecarboxamide (0.20 g, 0 , 49 mmol) in ethanol: water (10: 1, 20 ml) was heated for 3 hours in the presence of iron powder (82 mg, 1.47 mmol) under reflux. The reaction mixture was filtered, the filtrate was concentrated in vacuo and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 150 mg (81%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 0.74-0.76 (m, 4H, CH ₂ ) 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 1.72- 1.75 (m, 1H, CH) 2.82 (sept., J = 6.9 Hz, 1H, CH) 6.64 (m, 2H, ArH) 6.84-6.86 (m, 1H, ArH) 6.97-6.99 (m, 1H, ArH) 7.42 (m, 2H, ArH).

<EXAMPLE 159> 1- (4b-Hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl ) -3- (4-methoxyphenyl) thiourea

1- (4b-Hydroxy-6,8-diisopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- (4-methoxyphenyl) thiourea (100 mg, 0.78 mmol) was dissolved in ethanol: water (10 ml: 1 ml). To this solution was added Fe (319 mg, 5.7 mmol) and one drop conc. HCl and heated for 1 hour at the boil under reflux. Concentration in vacuo and purification by column chromatography (20% methanol in methylene chloride) gave the title compound. 60 mg, (64%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.22 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.9 Hz, 1H, CH) 3.80 (s, 3H, OCH ₃ ), 5.88 (d, J = 7.3 Hz, 1H, ArH), 6.64 ~ 6.67 (m, 2H, ArH), 6.85 ~ 6.89 (m, 3H, ArH), 6.98 ~ 7.01 (m, 2H, ArH), 7.16 (t, J = 7.8 Hz, 1H, ArH), 7.43 (d, J = 8.0 Hz, 1H, ArH).

<EXAMPLE 160> 1- (4b-Hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl ) -3- (phenyl) thiourea

1- (4b-Hydroxy-6,8-diisopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- (phenyl) thiourea (100 mg, 0.78 mmol) was dissolved in ethanol: water (10 ml: 1 ml). To this solution was added Fe (319 mg, 5.7 mmol) and one drop conc. HCl and heated under reflux for 1 hour. Concentration in vacuo and purification by column chromatography (20% methanol in methylene chloride) gave the title compound. 40 mg, (43%).

¹ H-NMR (300 MHz, acetone-d ₆ ) δ 1.21 (dd, J = 6.9 Hz, 1.0 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.9 Hz, 1H, CH), 5.79 (s, 1H, OH), 5.86 (d, J = 7.3 Hz, 1H, ArH), 6.43 (s, 2H, NH ₂ ), 6, 71 (d, J = 8.0 Hz, 1H, ArH), 6.74 (d, J = 1.4 Hz, 1H, ArH), 6.85 (dd, J = 8.0 Hz, 1.4 Hz, 1H, ArH), 7.12 ~ 7.22 (m, 3H, ArH), 7.32 ~ 7.35 (m, 3H, ArH), 7.45 (d, J = 8.0 Hz, 1H, ArH), 8.73 (s, 1H, NH), 8.78 (s, 1H, NH).

<EXAMPLE 161> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) thiophene-2-carboxamide

Thiophenecarboxylic acid (0.13 g, 1.01 mmol) was dissolved in anhydrous methylene chloride (10 ml) and stirred overnight at 0 ° C in the presence of EDCI (0.19 g, 1.01 mmol) and HOBt (0.13 g, 1.01 mmol). Since the reaction did not complete despite such a long period of time, EDCI (0.19 g, 1.01 mmol) and HOBt (0.13 g, 1.01 mmol) were additionally added. However, the completion of the reaction was not detected. The reaction mixture was diluted with methylene chloride and washed with water. The organic layer was dried and filtered. Purification by column chromatography (ethyl acetate: hexane = 1: 4) gave the title compound. 0.12 g (29%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.13-1.15 (m, 6H, CH ₃ ) 2.76-2.85 (m, 1H, CH) 6.71 (s, 1H, NH ) 6.80 (d, J = 7.8 Hz, 1H, ArH) 7.05 (s, 1H, ArH) 7.20 (s, 1H, ArH) 7.33 (d, J = 7.8 Hz , 1H, ArH) 7.50-7.55 (m, 2H, ArH) 7.61 (d, J = 2.4 Hz, 1H, ArH) 7.76-7.87 (m, 2H, ArH) 8.01 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 162> 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4 -methoxyphenyl) urea

1- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-methoxyphenyl) urea (93 mg, 0.19 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to form a pale yellow cloudy solution, to which was then added Fe powder (39 mg, 0.70 mmol) and two drops of conc . HCl at room temperature, followed by stirring for 1.5 hours at the boil under reflux. A new spot was observed just below the starting material according to TLC. The reaction mixture was filtered, concentrated and purified by silica gel column chromatography using EtOAc / Hx (1 / 2-1 / 1) to obtain the title compound as a pale yellow solid (65 mg, 0.14 mmol, 74%).

¹ H-NMR (300 MHz, CDCl ₃ + 2 drops of CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H), 2.38 (s, br, 5H), 2.82 ( hept., J = 6.9 Hz, 1H), 3.78 (s, 3H), 6.07 (d, J = 7.4 Hz, 1H), 6.58 (d, J = 8.2 Hz , 1H), 6.68 (d, J = 1.5 Hz, 1H), 6.81-6.87 (m, 1H), 6.84 (d, J = 9.0 Hz, 2H), 7 08 (d, J = 9.0 Hz, 2H), 7.17 (t, J = 7.8 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H).

<EXAMPLE 163> 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-butylurea

1-Butyl-3- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea (100 mg, 0.228 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to form a pale yellow cloudy solution, to which was then added Fe powder (38 mg, 0.680 mmol) and two drops conc. HCl at room temperature, followed by stirring for 2.5 hours at the boil under reflux. A new spot was observed just below the starting material according to TLC. The reaction mixture was filtered, concentrated and purified by silica gel column chromatography using EtOAc / Hx (1 / 2-1 / 1) to give the title compound as a pale yellow solid (66 mg, 0.16 mmol , 71%).

¹ H-NMR (300 MHz, CDCl ₃ + drop of CD ₃ OD) δ 0.87 (t, J = 7.2 Hz, 3H), 1.16 (dd, J = 6.9, 0.8 Hz, 6H), 1.27 (sext., J = 7.4 Hz, 2H), 1.36-1.65 (m, 2H), 2.10 (s, br., 3H), 2.79 (hept ., J = 6.9 Hz, 1H), 3.16-3.28 (m, 1H), 3.32-3.44 (m, 1H), 6.63 (d, J = 8.2 Hz , 1H), 6.69 (d, J = 1.5 Hz, 1H), 7.76 (dd, J = 8.1, 1.6 Hz, 1H), 6.93 (d, J = 7, 3 Hz, 1H), 7.15 (d, J = 8.0 Hz, 1H), 7.42 (dd, J = 8.1, 7.4 Hz, 1H).

<EXAMPLE 164> 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4 -fluorophenyl) urea

1- (4-Fluorophenyl) -3- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea (187 mg, 0.392 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to form a pale yellow hazy solution, to which was then added Fe powder (66 mg, 1.18 mmol) and one drop conc. HCl at room temperature, followed by stirring for 1 hour at the boil under reflux. A new spot was observed just below the starting material according to TLC. The reaction mixture was filtered, concentrated and purified by silica gel column chromatography using EtOAc / Hx (1 / 2-1 / 1) to give the title compound as a pale yellow solid (107 mg, 0.239 mmol, 61 %).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.23 (d, J = 6.9 Hz, 6H), 2.85 (hept., J = 6.9 Hz, 1H), 5.87 ( d, J = 7.3 Hz, 1H), 6.64-6.67 (m, 2H), 6.87 (dd, J = 8.0, 1.6 Hz, 1H), 7.05-7 20 (m, 5H); 7.48 (d, J = 6.5 Hz, 1H).

<EXAMPLE 165> 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (t -butyl) urea

1- (tert-Butyl) -3- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea (99 mg, 0.23 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to form a pale yellow hazy solution, to which was then added Fe powder (38 mg, 0.688 mmol) and two drops conc. HCl at room temperature, followed by stirring for 1.5 hours at the boil under reflux. A new spot (PK344) was observed just below the starting material according to TLC. The reaction mixture was filtered, concentrated and purified by silica gel column chromatography using EtOAc / Hx (1 / 2-1 / 1) to give the title compound as a yellow solid (84 mg, 0.21 mmol, 91 %).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (dd, J = 6.9, 1.9 Hz, 6H), 1.23 (s, 9H), 2.73-2.88 ( m, 1H), 6.58-6.72 (m, 2H), 6.81 (d, br, J = 7.3 Hz, 1H), 6.99 (d, br, J = 6, 9 Hz, 1H), 7.31 (d, broad, J = 7.2 Hz, 1H), 7.38-7.52 (m, 1H).

<EXAMPLE 166> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide (123 mg, 0.334 mmol) was added to 5 ml of EtOH: H ₂ O (10: 1) to form a pale yellow cloudy solution, to which was then added Fe powder (46 mg, 0.83 mmol) and one drop conc. HCl at room temperature, followed by stirring for 2 hours at the boil under reflux. A new spot was observed just below the starting material according to TLC. The reaction mixture was filtered, concentrated and purified by silica gel column chromatography using EtOAc / Hx (1 / 2-1 / 1) to give the title compound as a yellow solid (72 mg, 0.21 mmol, 64 %).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (dd, J = 6.9, 1.4 Hz, 6H), 2.83 (hept., J = 6.9 Hz, 1H), 6.66 (s, 1H), 6.68-6.76 (m, 1H), 6.84 (d, J = 7.9 Hz, 1H), 7.00 (d, J = 7.1 Hz , 1H), 7.33 (d, J = 7.9 Hz, 1H), 7.41-7.50 (m, 1H), 8.10 (s, 1H).

<EXAMPLE 167> N- (1-Formamido-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide

A mixture of formic acid (5 ml) and acetic anhydride (10 ml) was stirred at 80 ° C for 30 minutes, and then cooled to room temperature. To this mixture was added a solution of N- (1-amino-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide (200 mg , 0.57 mmol) in methylene chloride, followed by stirring at room temperature. After removing the solvent and adding a small amount of methylene chloride, a white precipitate formed. It was filtered to give the title compound (170 mg, 79%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (dd, J = 6.9 Hz, 1.6 Hz, 6H, CH ₃ ), 1.99 (s, 3H, CH ₃ ), 2 82 (sept., J = 6.9 Hz, 1H, CH), 6.65 (s, 1H, CH ₃ ), 6.88 (dd, J = 7.9 Hz, 1.0 Hz, 1H, ArH), 7.38 (d, J = 7.9 Hz, 1H, ArH), 7.59 (d, J = 7.6 Hz, 1H, ArH), 7.75 (t, J = 8.0 Hz, 1H, ArH), 8.46 (s, 1H), 8.50 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 168> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide

To N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide (150 mg , 0.36 mmol) was added a mixture of ethanol: water (10 ml: 1 ml), Fe (80 mg, 1.43 mmol) and two drops conc. HCl in that order. After heating for 2 hours under reflux, the reaction mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: n-hexane = 1: 2) to obtain the title compound (60 mg, 43%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.34 (d, J = 6.9 Hz, 6H, CH ₃ ), 3.09 (sept., J = 6.9 Hz, 1H, CH) 3.34 (s, 3H, SCH ₃ ), 7.11 (d, J = 7.7 Hz, 1H, ArH), 7.28-7.35 (m, 2H, ArH), 7.56 ( s, 1H, ArH), 7.73 (d, J = 7.9 Hz, 1H, ArH), 7.81 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 169> Diethyl- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) phosphoamidate

Diethyl- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) phosphoamidate (0.050 g, 0.11 mmol ) was dissolved in a mixture of ethanol: water (10: 1, 10 ml). To this solution was added iron powder (20 mg, 0.36 mmol) and 2-3 drops conc. HCl before heating for 2.5 hours at the boil under reflux. After completion of the reaction, the reaction mixture was washed with ethyl acetate, filtered to remove iron powder, and extracted with ethyl acetate and water. The organic layer was washed with brine, dried and concentrated, followed by separation and purification by column chromatography (30% ethyl acetate mixed with 50% hexane) to obtain the title compound. 6 mg (13%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.13 (t, J = 6.9 Hz, 6H, CH ₃ ) 1.26 (d, J = 6.9 Hz, 6H, CH ₃ ) 2 88 (sept., J = 6.9 Hz, 1H, CH) 3.65-3.89 (m, 4H, CH ₂ ) 6.69 (d, J = 7.8 Hz, 1H, ArH) 6 , 83-6.86 (m, 2H, ArH) 7.03 (d, J = 7.8 Hz, 1H, ArH) 7.30 (d, J = 8.1 Hz, 1H, ArH) 7.40 (t, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 170> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-cyanobenzamide

Iron powder (30 mg, 0.38 mmol) and 3 drops conc. HCl was added to a solution of 4-cyano-N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide (0.06 g, 0.13 mmol) in ethanol: water (10: 1, 20 ml) and heated for 3 hours at the boil under reflux. After completion of the reaction, the reaction mixture was washed with ethyl acetate, filtered to remove iron powder, and extracted with ethyl acetate and water. The organic layer was washed with brine, dried and concentrated, followed by separation and purification by column chromatography (30% ethyl acetate, mixed with 30% hexane) to obtain the title compound. 50 mg (89%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 6 67 (br., 2H, ArH) 6.86-6.88 (m, 1H, ArH) 7.00-7.02 (m, 1H, ArH) 7.43-7.45 (m, 2H, ArH) 7.77-7.80 (m, 2H, ArH) 7.96-7.99 (m, 2H, ArH).

<EXAMPLE 171> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-naphthamide

Iron powder (35 mg, 0.60 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-naphthamide ( 0.10 g, 0.20 mmol) in ethanol: water (10: 1, 10 ml) and was heated for 3 hours at the boil under reflux. After completion of the reaction, the reaction mixture was washed with ethyl acetate, filtered to remove iron powder, and extracted with ethyl acetate and water. The organic layer was washed with brine, dried and concentrated, followed by separation and purification by column chromatography (30% ethyl acetate, mixed with 40% hexane) to obtain the title compound. 85 mg (90%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.86 (sept., J = 6.9 Hz, 1H, CH) 6 68-6.72 (m, 2H, ArH) 6.90 (d, J = 7.5 Hz, 1H, ArH) 7.03 (d, J = 7.5 Hz, 1H, ArH) 7.44 -7.59 (m, 4H, ArH) 7.89-7.97 (m, 4H, ArH) 8.45 (s, 1H, ArH).

<EXAMPLE 172> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - [1,1 'Biphenyl] -4-carboxamide

Iron powder (33 mg, 0.58 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - [1,1 Β-biphenyl] -4-carboxamide (0.10 g, 0.19 mmol) in ethanol: water (10: 1, 10 ml) and heated for 3 hours at the boil under reflux. After completion of the reaction, the reaction mixture was washed with ethyl acetate, filtered to remove iron powder, and extracted with ethyl acetate and water. The organic layer was washed with brine, dried and concentrated, followed by separation and purification by column chromatography (30% ethyl acetate, mixed with 30% hexane) to obtain the title compound. 85 mg (90%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.85 (sept., J = 6.9 Hz, 1H, CH) 6 68-6.76 (m, 2H, ArH) 6.89 (d, J = 8.1 Hz, 1H, ArH) 7.02 (d, J = 7.2 Hz, 1H, ArH) 7.34 = 7.45 (m, 5H, ArH) 7.53-7.59 (m, 4H, ArH) 7.92-7.94 (m, 2H, ArH).

<EXAMPLE 173> 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-ethylurea

Fe (61 mg, 1.09 mmol) and 2 drops conc. HCl was added to a solution of 1- (1-nitro-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-ethylurea (150 mg, 0.36 mmol) in ethanol: water (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a white solid (50 mg, 36%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.08 (t, J = 7.1 Hz, 3H, CH ₃ ), 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80 (sept., J = 6.9 Hz, 1H, CH), 3.32 ~ 3.43 (m, 2H, CH ₂ ), 6.60 (d, J = 1.3 Hz, 1H , ArH), 6.70 (d, J = 8.2 Hz, 1H, ArH), 6.79 (dd, J = 8.0 Hz, 1.3 Hz, 1H, ArH), 6.91 (d , J = 7.3 Hz, 1H, ArH), 7.36 ~ 7.44 (m, 2H, ArH).

<EXAMPLE 174> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) tetrahydrofuran -2-carboxamide

Fe (38 mg, 0.68 mmol) and 2 drops conc. HCl was added to a solution of 2N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) tetrahydrofuran -2-carboxamide (100 mg, 0.23 mmol) in a mixture of ethanol: water (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a white solid (70 mg, 75%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.14 (d, J = 6.9 Hz, 6H, CH ₃ ), 1.78 ~ 2.08 (m, 3H, CH ₂ ), 2, 11 ~ 2.23 (m, 1H, CH ₂ ), 2.80 (sept., J = 6.9 Hz, 1H, CH), 3.75 ~ 3.87 (m, 1H, OCH ₂ ), 3 , 91 ~ 4.04 (m, 1H, OCH ₂ ), 4.30 ~ 4.34 (m, 1H, OCH), 6.63 ~ 6.67 (m, 2H, ArH), 6.83 (d , J = 7.9 Hz, 1H, ArH), 6.98 (d, J = 7.3 Hz, 1H, ArH), 7.32 ~ 7.43 (m, 2H, ArH).

<EXAMPLE 175> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2.2, 2-trifluoroacetamide

Iron powder (0.10 g, 1.8 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of 2,2,2-trifluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide (0.11 g, 0.25 mmol) in absolute ethanol (8 ml) and heated for 3 hours at the boil under reflux . The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and subjected to column chromatography for 30 min (ethyl acetate: hexane = 1: 4) filled with Et ₃ N-treated silica gel to give the title compound. 90 mg (90%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80-2.85 (m, 1H, CH) 6.66-6 72 (m, 2H, ArH) 6.86 (d, J = 7.8 Hz, 1H, ArH) 6.98 (d, J = 7.2 Hz, 1H, ArH) 7.33-7.36 (m, 1H, ArH) 7.45 (t, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 176> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 1,1,1-trifluoromethanesulfonamide

Fe (60 mg, 1.08 mmol) and 2 drops conc. HCl was added to a solution of 1,1,1-trifluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b ] furan-9b-yl) methanesulfonamide (170 mg, 0.36 mmol) in ethanol: water (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a white solid (140 mg, 88%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (dd, J = 6.9 Hz, 1.6 Hz, 6H, CH ₃ ), 2.82 (sept., J = 6.9 Hz , 1H, CH), 6.64 (s, 1H, ArH), 6.67 (d, J = 8.2 Hz, 1H, ArH), 6.85 (d, J = 7.7 Hz, 1H, ArH), 7.00 (d, J = 7.4 Hz, 1H, ArH), 7.35 (d, J = 8.0 Hz, 1H, ArH), 7.45 (t, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 177> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide

A mixture of formic acid (2.5 ml) and acetic anhydride (5.0 ml) was stirred at 80 ° C for 30 min, and then cooled to room temperature before adding a solution of 9b-amino-4b-hydroxy-7-isopropyl-4bH -benzo [d] indeno [1,2-b] furan-10 (9bH) -one (400 mg, 1.35 mmol) in DCM. The resulting reaction mixture was stirred at room temperature for 1 hour, concentrated, extracted with ethyl acetate and water, and re-concentrated in vacuo. The concentrate was purified by silica gel column chromatography (30% ethyl acetate was stirred with 30% hexane) to obtain the title compound. 140 mg (32%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (dd, J = 6.9 Hz, J = 2.4, 6H, CH ₃ ) 2.82 (hept., J = 6.9 Hz, 1H, CH) 6.65 (s, 1H, ArH / NH / OH) 6.87 (d, J = 7.8 1H, ArH) 7.35 (d, J = 7.8, 1H, ArH.) 7.65-7.80 (m, 2H, ArH); 7.81-7.9 (m, 2H, ArH); 8.10 (s, 1H, NH / CHO).

<EXAMPLE 178> 1,1,1-Trifluoro-N- (4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide

Methanesulfonic anhydride (229 mg, 0.81 mmol) and triethylamine (123 mg, 1.22 mmol) were added to the solution of 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2.1 -a] inden-10-one (200 mg, 0.68 mmol) in methylene chloride (10 ml) and stirred at room temperature for 4 hours. After concentration in vacuo, purification by column chromatography (ethyl acetate: hexane = 1: 2) gave the title compound as a red solid (220 mg, 32%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.81 (sept., J = 6.9 Hz, 1H, CH), 6.68 (s, 1H, ArH), 6.81 (d, J = 7.6 Hz, 1H, ArH), 7.54 (d, J = 7.9 Hz, 1H, ArH), 7.51 (t, J = 7.5 Hz, 1H, ArH), 7.75 ~ 7.82 (m, 2H, ArH), 8.01 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 179> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-phenylacetamide

Iron powder (61 mg, 1.09 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-phenylacetamide (0.10 g, 0.22 mmol) in ethanol: water (10: 1, 10 ml) and heated for 12 hours at the boil under reflux. The reaction mixture was filtered to remove iron powder and was extracted with ethyl acetate and water. The organic layer was washed with brine, concentrated in vacuo, and purified by silica gel column chromatography (50% ethyl acetate in hexane) to obtain the title compound. 75 mg (81%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.82 (sept., J = 6.9 Hz, 1H, CH) 3 59 (s, 2H, CH ₂ ) 6.64 (br, 2H, ArH) 6.83 (br, 1H, ArH) 6.96-6.98 (br, 1H, ArH) 7.19 -7.41 (m, 6H, ArH).

<EXAMPLE 180> (E) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - 3- (3,4-dichlorophenyl) acrylamide

Iron powder (42 mg, 0.74 mmol) and 3 drops conc. HCl was added to a solution of (E) -3- (3,4-dichlorophenyl) -N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acrylamide (0.08 g, 0.15 mmol) in ethanol: water (10: 1, 10 ml) and was heated for 12 hours at the boil under reflux. The reaction mixture was filtered to remove iron powder and was extracted with ethyl acetate and water. The organic layer was washed with brine and concentrated in vacuo. A small amount of methanol was added to the concentrate to form a precipitate, which was then filtered to obtain the title compound. 30 mg (80%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6.9 Hz, 1H, CH) 6 66-6.79 (m, 3H, ArH) 6.86-6.88 (m, 1H, ArH) 6.99-7.01 (m, 1H, ArH) 7.34-7.54 (m 5H, ArH) 7.74 (s, 1H, ArH).

<EXAMPLE 181> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4- (benzyloxy )benzamide

Iron powder (26 mg, 0.47 mmol) and 2 drops conc. HCl was added to a solution of 4-benzyl-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) benzamide (0.05 g, 0.094 mmol) in ethanol: water (10: 1, 10 ml) and heated for 6 hours at the boil under reflux. After removing the iron powder by filtration, the reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and concentrated in vacuo. A small amount of methanol was added to the concentrate to form a precipitate, which was then filtered to obtain the title compound. 15 mg (32%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 5 12 (s, 2H, CH ₂ ) 6.67 (s, 2H, ArH) 6.85 (s, 1H, ArH) 7.00-7.03 (s, 3H, ArH) 7.18-7, 43 (m, 7H, ArH) 7.80-7.83 (m, 2H, ArH).

<EXAMPLE 182> 2 - ([1,1′-Biphenyl] -4-yl) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) acetamide

Iron powder (31.3 mg, 0.56 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) biphenyl -4-carboxamide (0.1 g, 0.18 mmol) in ethanol: water (10: 1, 10 ml) and heated for 4 hours at the boil under reflux. After removing the iron powder by filtration, the reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and concentrated in vacuo. A small amount of methanol was added to the concentrate to form a precipitate, which was then filtered to obtain the title compound. 50 mg (54%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 3 64 (s, 2H, CH ₂ ) 6.65 (s, 2H, ArH) 6.83-6.86 (br, 1H, ArH) 6.98 (br, 1H, ArH) 7.27- 7.43 (m, 7H, ArH); 7.53-7.60 (m, 4H, ArH).

<EXAMPLE 183> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxybenzamide

Iron powder (0.13 g, 2.46 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -2-methoxybenzamide (0.16 g, 0.33 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was purified for 30 minutes using column chromatography (ethyl acetate: hexane = 1: 4) filled with Et ₃ N-treated silica gel to give the title compound (80 mg, 54%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.22-1.23 (m, 6H, CH ₃ ) 2.81-2.90 (sept., 1H, CH) 4.00 (s, 3H , OCH ₃ ) 6.71 (s, 1H, ArH) 6.86 (s, 1H, ArH) 7.04-7.07 (m, 2H, ArH) 7.12-7.15 (m, 2H, ArH) 7.50-7.55 (m, 3H, ArH) 7.94 (s, 1H, ArH).

<EXAMPLE 184> tert-Butyl (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b- ilamino) -1-oxopropan-2-ylcarbamate

EDCI (233 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) were added to a solution of Boc-L-alanine (231 mg, 1.22 mmol) in methylene chloride (20 ml). After 20 minutes, 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol) was added to the solution and stirred overnight at room temperature. After completion of the reaction, the reaction mixture was extracted with methylene chloride and water, and the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound (368 mg, 77%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 1.33 ~ 1.47 (m, 9H, CH ₃ ), 1.59 (s, 3H, CH ₃ ), 2.81 (sept., J = 6.9 Hz, 1H, CH), 4.19 (m, 1H), 4.88 (m, 1H), 5.56 ( s, 1H), 6.69 (s, 1H, ArH), 6.79-6.83 (m, 1H, ArH), 7.28 (m, 1H, ArH), 7.54 (t, J = 7.4 Hz, 1H, ArH), 7.76-7.81 (m, 2H, ArH), 7.99 (d, J = 7.6 Hz, 1H, ArH).

<EXAMPLE 185> tert-Butyl (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b- ilamino) -1-oxo-3-phenylpropan-2-ylcarbamate

EDCI (233 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) were added to a solution of Boc-L-phenylalanine (324 mg, 1.22 mmol) in methylene chloride (20 ml). After 20 minutes, 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol) was added to the solution and stirred overnight at room temperature. After completion of the reaction, the reaction mixture was extracted with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purified by column chromatography (ethyl acetate: n-hexane = 1: 2) to obtain the title compound (480 mg, 87%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.13 (9 m, 6H, CH ₃ ), 1.40 (m, 1H, CH), 2.99-3.12 (m, 2H, CH ₂ ), 4.29-4.42 (m, 1H, CH), 4.90-5.01 (m, 1H, CH), 6.68 (s, 1H, ArH), 6.76-6.84 (m, 1H, ArH), 7.10-7.21 (m, 3H, ArH), 7.27-7.34 (m, 3H, ArH), 7.48-7.55 (m, 1H, ArH), 7.75-7.80 (m, 2H, ArH), 7.96-8.01 (m, 1H, ArH).

<EXAMPLE 186> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-methylbenzamide

Fe (66 mg, 1.18 mmol) and 2 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-methylbenzamide (180 mg, 0.39 mmol) in ethanol: H ₂ O (20 ml: 2 ml) and heated for 2.5 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 3) to obtain the title compound as a yellow solid (134 mg, 80%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.16 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.45 (s, 3H, ArH), 2.82 (sept., J = 6.8 Hz, 1H, CH), 6.64 (s, 1H, ArH), 6.68 (d, J = 8.3 Hz, 1H, ArH), 6.85 (d, J = 7 , 3 Hz, 1H, ArH), 7.03 (d, J = 7.3 Hz, 1H, ArH), 7.18-7.22 (m, 2H, ArH), 7.30 (t, J = 7.4 Hz, 1H, ArH), 7.41-7.46 (m, 2H, ArH), 7.51 (d, J = 7.3 Hz, 1H, ArH).

<EXAMPLE 187> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-methylbenzamide

Fe (66 mg, 1.18 mmol) and 2 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-methylbenzamide (1800 mg, 0.39 mmol) in ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 3) to obtain the title compound as a yellow solid (88 mg, 52%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (dd, J = 6.9 Hz, 1.4 Hz, 6H, CH ₃ ), 2.36 (s, 3H, ArH), 2, 84 (sept., J = 6.8 Hz, 1H, CH), 6.67-6.70 (m, 2H, ArH), 6.87-6.88 (m, 1H, ArH), 7.02 -7.03 (m, 1H, ArH), 7.28-7.35 (m, 2H, ArH), 7.45 (m, 1H, ArH), 7.63 (d, J = 7.6 Hz , 1H, ArH); 7.67 (s, 1H, ArH).

<EXAMPLE 188> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4-methylbenzamide

Fe (59 mg, 1.05 mmol) and 2 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4-methylbenzamide (160 mg, 0.35 mmol) in ethanol: H ₂ O (20 ml: 2 ml) and heated for 4 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 3) to obtain the title compound as a yellow solid (106 mg, 71%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.16 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.35 (s, 3H, ArH), 2.81 (sept., J = 6.8 Hz, 1H, CH), 6.65-6.69 (m, 2H, ArH), 6.86 (d, J = 7.4 Hz, 1H, ArH), 7.00 (d , J = 7.4 Hz, 1H, ArH), 7.22 (d, J = 7.5 Hz, 1H, ArH), 7.41-7.46 (m, 2H, ArH), 7.74 ( d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 189> Methyl-4- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamoyl )benzoate

Fe (93 mg, 1.67 mmol) and 2 drops conc. HCl was added to a solution of methyl 4- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamoyl ) benzoate (280 mg, 0.56 mmol) in ethanol: H ₂ O (20 ml: 2 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 3) to obtain the title compound as a yellow solid (186 mg, 71%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.16 (d, J = 6.5 Hz, 6H, CH ₃ ), 2.81 (sept., J = 6.5 Hz, 1H, CH) 3.89 (s, 3H, OCH ₃ ), 6.65 ~ 6.68 (m, 2H, ArH), 6.86 (d, J = 7.4 Hz, 1H, ArH), 7.02 ( d, J = 6.9 Hz, 1H, ArH), 7.41 ~ 7.46 (m, 2H, ArH), 7.93 (d, J = 8.1 Hz, 2H, ArH), 8.04 (d, J = 8.0 Hz, 2H, ArH).

<EXAMPLE 190> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chlorobenzamide

Iron powder (0.17 g, 3.04 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of 3-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH- indeno [1,2-b] benzofuran-9b-yl) benzamide (0.20 g, 0.41 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was basified with NaHCO ₃ , washed repeatedly with water, and the organic layer was dried, filtered and subjected to column chromatography for 30 minutes (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to obtain the title compound. 90 mg (93%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (dd, J = 6.9, 2.1 Hz, 6H, CH ₃ ) 2.85-2.87 (sept., 1H, CH) 6.68-6.78 (m, 2H, ArH) 6.82-6.86 (m, 1H, ArH) 6.95-7.03 (m, 1H, ArH) 7.38-7.60 ( m, 4H, ArH) 7.77-7.79 (m, 1H, ArH) 7.87-7.90 (m, 1H, ArH).

<EXAMPLE 191> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3,5- dimethylbenzamide

Iron powder (0.04 g, 0.77 mmol), conc. HCl (0.01 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -3,5-dimethylbenzamide (50 mg, 0.10 mmol) in absolute ethanol (5 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was basified with NaHCO ₃ and washed several times with water, the organic layer was dried, filtered and subjected to column chromatography for 30 min (ethyl acetate: hexane = 1: 4) filled with silica gel treated with Et ₃ N to obtain the title compound. 30 mg (68%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18-1.20 (m, 6H, CH ₃ ) 2.33 (s, 6H, CH ₃ ) 2.81-2.87 (sept., 1H, CH) 6.67-6.70 (m, 2H, ArH) 6.84-6.86 (m, 1H, ArH) 7.03-7.05 (m, 1H, ArH) 7.18 ( s, 1H, ArH) 7.46 (s, 4H, ArH).

<EXAMPLE 192> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2.4, 6-trichlorobenzamide

Iron powder (37 mg, 0.66 mmol) and 2 drops conc. HCl was added to a solution of 2,4,6-trichloro-N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b -yl) benzamide (0.12 g, 0.22 mmol) in ethanol: water (10: 1, 10 ml) and heated for 3 hours at the boil under reflux. After completion of the reaction, the reaction mixture was washed with ethyl acetate, filtered to remove iron powder, and extracted with ethyl acetate and water. The organic layer was washed with brine, dried, concentrated and purified by column chromatography (30% ethyl acetate mixed with 20% hexane) to give the title compound. 85 mg (75%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 6 62-6.75 (m, 2H, ArH) 6.83 (m, 1H, ArH) 7.05 (m, 1H, ArH) 7.36-7.54 (m, 3H, ArH) 7.89 (s, 1H, ArH).

<EXAMPLE 193> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-fluoroacetamide

Fe (63 mg, 1.12 mmol) and 3 drops conc. HCl was added to a solution of 2-fluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) acetamide (150 mg, 0.37 mmol) in ethanol: H ₂ O (20 ml: 2 ml) and heated for 2.5 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (EtOAc: hexane = 1: 1) to obtain the title compound as a yellow solid (63 mg, 46%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.3 Hz, 6H, CH ₃ ), 2.82 (sept., J = 6.3 Hz, 1H, CH) 4.84 (d, J = 45 Hz, 2H, CH ₂ F), 6.65-6.68 (m, 2H, ArH), 6.84-6.87 (m, 1H, ArH), 6 97-6.99 (m, 1H, ArH); 7.35-7.45 (m, 2H, ArH).

<EXAMPLE 194> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-chloroacetamide

Fe (45 mg, 0.79 mmol) and 3 drops conc. HCl was added to a solution of 2-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) acetamide (110 mg, 0.26 mmol) in ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (EtOAc: hexane = 1: 1) to obtain the title compound as a yellow solid (98 mg, 97%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.81 (sept., J = 6.9 Hz, 1H, CH) 4.10 (d, J = 4.0 Hz, 2H, CH ₂ Cl), 6.64-6.67 (m, 2H, ArH), 6.83-6.87 (m, 1H, ArH) 6.98 (d, J = 7.3 Hz, 1H, ArH); 7.35-7.42 (m, 2H, ArH).

<EXAMPLE 195> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2,2-dichloroacetamide

Fe (36 mg, 0.65 mmol) and 2 drops conc. HCl was added to a solution of 2,2-dichloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan -9b-yl) acetamide (90 mg, 0.22 mmol) in ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (EtOAc: hexane = 1: 2) to obtain the title compound as a yellow solid (62 mg, 74%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.6 Hz, 6H, CH ₃ ), 2.81 (sept., J = 6.6 Hz, 1H, CH) 6.06 (t, J = 5.4 Hz, 1H, CHF2), 6.65-6.68 (m, 2H, ArH), 6.84-6.87 (m, 1H, ArH), 6 97-6.99 (m, 1H, ArH); 7.35-7.45 (m, 2H, ArH).

<EXAMPLE 196> 1-amino-9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran- 10 (9bH) -one

Solution 9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan -10 (9bH) -one (0.080 g, 0.18 mmol) in ethanol: water (10: 1, 10 ml) was heated for 23 hours at the boil under reflux in the presence of iron powder (38 mg, 0.68 mmol ) The reaction mixture was washed with ethyl acetate and filtered to remove iron powder, followed by extraction with ethyl acetate and water. Separation and purification by silica gel column chromatography (30% ethyl acetate mixed with 50% hexane) gave the title compound. 50 mg (67%).

¹ H-NMR (300 MHz, CD ₃ OD): δ 0.93 (t, J = 7.2 Hz, 3H, CH ₃ ) 1.23 (d, J = 6.9 Hz, 6H, CH ₃ ) 1.33-1.41 (m, 2H, CH ₂ ) 1.58-1.68 (m, 2H, CH ₂ ) 2.69 (t, J = 7.2 Hz, 2H, CH ₂ ) 2, 90 (sept., J = 6.9 Hz, 1H, CH) 6.79 (br, 2H, ArH) 6.98-7.03 (m, 2H, ArH) 7.22-7.41 (m , 2H, ArH) 7.50-7.55 (m, 1H, ArH).

<EXAMPLE 197> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide

Iron powder (0.18 g, 3.2 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) picolinamide (0.20 g, 0.44 mmol) in absolute ethanol (8 ml) and heated for 4 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2 to methylene chloride: MeOH = 20: 1) filled with silica gel treated with Et ₃ N to give the title compound. 80 mg (43%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83-2.87 (m, 1H, CH) 6.70 (s , 2H, ArH) 6.89 (d, J = 7.2 Hz, 1H, ArH) 7.02 (d, J = 7.2 Hz, 1H, ArH) 7.45-7.48 (m, 2H , ArH) 7.55 (t, J = 6.0 Hz, 1H, ArH) 7.90-7.97 (m, 2H, ArH) 8.62 (d, J = 3.6 Hz, 1H, ArH )

<EXAMPLE 198> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide

Iron powder (0.18 g, 3.2 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) nicotinamide (0.20 g, 0.44 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2 to methylene chloride: MeOH = 20: 1) filled with silica gel treated with Et ₃ N to give the title compound. 140 mg (75%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.79-2.88 (m, 1H, CH) 6.67-6 70 (m, 2H, ArH) 6.88 (d, J = 7.8 Hz, 1H, ArH) 7.01 (d, J = 7.2 Hz, 1H, ArH) 7.43-7.51 (m, 3H, ArH) 8.25 (d, J = 8.1 Hz, 1H, ArH) 8.65 (d, J = 3.9 Hz, 1H, ArH) 9.00 (s, 1H, ArH )

<EXAMPLE 199> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isonicotinamide

Iron powder (0.09 g, 16.3 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isonicotinamide (0.10 g, 0.22 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N to afford the title compound. 62 mg (68%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.82-2.86 (m, 1H, CH) 6.67-6 71 (s, 2H, ArH) 6.89 (d, J = 7.5 Hz, 1H, ArH) 7.01 (d, J = 7.2 Hz, 1H, ArH) 7.43-7.48 (m, 2H, ArH) 7.79-7.80 (m, 2H, ArH) 8.64-8.66 (m, 2H, ArH).

<EXAMPLE 200> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazine-2-carboxamide

Iron powder (0.09 g, 1.63 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) pyrazin-2-carboxamide (0.10 g, 0.22 mmol) in absolute ethanol (8 ml) and heated for 3 hours at the boil under reflux . The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N to afford the title compound. 90 mg (98%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.80-2.89 (m, 1H, CH) 6.69-6 72 (m, 2H, ArH) 6.89 (d, J = 8.1 Hz, 1H, ArH) 7.02 (d, J = 7.2 Hz, 1H, ArH) 7.43-7.49 (m, 2H, ArH) 8.66 (s, 1H, ArH) 8.78 (s, 1H, ArH) 9.14 (s, 1H, ArH).

<EXAMPLE 201> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide

Iron powder (0.09 g, 1.68 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) furan-2-carboxamide (0.10 g, 0.23 mmol) in absolute ethanol (8 ml) and heated for 2 hours under reflux . The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2) filled with silica gel treated with Et ₃ N to give the title compound. 52 mg (56%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.79-2.85 (m, 1H, CH) 6.56 (d , J = 1.5 Hz, 1H, ArH) 6.67 (s, 2H, ArH) 6.87 (d, J = 6.0 Hz, 1H, ArH) 7.00 (d, J = 6.0 Hz, 1H, ArH) 7.12 (d, J = 3.3 Hz, 1H, ArH) 7.43-7.51 (m, 2H, ArH) 7.64 (s, 1H, ArH).

<EXAMPLE 202> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide

Fe powder (35 mg, 0.60 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide (0.10 g, 0.20 mmol) in ethanol: water (10: 1, 10 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified by column chromatography (30% ethyl acetate was stirred with 40% hexane) to obtain the title compound. 80 mg (85%).

¹ H-NMR (300 MHz, CD ₃ OD): δ 1.23 (dd, J = 1.5 Hz, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., J = 6, 9 Hz, 1H, CH) 6.69 (s, 2H, ArH) 6.89 (s, 1H, ArH) 7.01 (s, 1H, ArH) 7.45-7.67 (m, 3H, ArH ) 7.72 (s, 1H, ArH) 8.14-8.17 (m, 1H, ArH) 8.46-8.58 (m, 2H, ArH) 8.86 (s, 1H, ArH).

<EXAMPLE 203> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide

Fe powder (68 mg, 1.21 mmol) and 3 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide (0.20 g, 0.40 mmol) in ethanol: water (10: 1, 20 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and recrystallized from 30% ethyl acetate mixed with 30% hexane to give the title compound. 130 mg

¹ H-NMR (300 MHz, CD ₃ OD): δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.85 (sept., J = 6.9 Hz, 1H, CH) 6.70 (br, 2H, ArH) 6.88-6.90 (m, 1H, ArH) 7.03-7.06 (m, 1H, ArH) 7.48 (br, 2H, ArH) 7.58-7.62 (m, 1H, ArH) 8.05-8.08 (m, 1H, ArH) 8.10-8.19 (m, 1H, ArH) 8.43-8.51 ( m, 2H, ArH) 8.91-8.93 (m, 1H, ArH).

<EXAMPLE 204> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran -2-carboxamide

Fe (69 mg, 1.24 mmol) and 2 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran -2-carboxamide (200 mg, 0.41 mmol) in ethanol: water (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After concentration in vacuo, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 1) to obtain the title compound as a white solid (118 mg, 63%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.12 (d, J = 6.7 Hz, 6H, CH ₃ ), 2.77 (sept., J = 6.7 Hz, 1H, CH) , 6.65 ~ 6.67 (m, 2H, ArH), 6.85 (d, J = 7.8 Hz, 1H, ArH), 7.03 (d, J = 7.3 Hz, 1H, ArH ), 7.24 (t, J = 7.4 Hz, 1H, ArH), 7.35-7.43 (m, 2H, ArH), 7.46-7.53 (m, 3H, ArH), 7.63 (d, J = 7.7 Hz, 1H, ArH).

<EXAMPLE 205> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-methylbenzofuran-2-carboxamide

Fe (67 mg, 1.2 mmol) and 2 drops conc. HCl was added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-methylbenzofuran-2-carboxamide (200 mg, 0.40 mmol) in a solvent ethanol: water (10 ml: 1 ml) and heated for 23 hours at the boil under reflux. After vacuum concentration, the reaction mixture was purified by column chromatography (ethyl acetate: n-hexane = 1: 1) to obtain the title compound as a white solid (162 mg, 86%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.49 (s, 3H, CH ₃ ), 2.85 (sept., J = 6.9 Hz, 1H, CH), 6.70 (m, 2H, ArH), 6.89 (m, 1H, ArH), 7.03 (m, 1H, ArH), 7.31 (t , J = 7.1 Hz, 1H, ArH), 7.42-7.55 (m, 4H, ArH), 7.66 (d, J = 7.7 Hz, 1H, ArH).

<EXAMPLE 206> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylthiazole- 5-carboxamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4-methylthiazole- 5-carboxamide (81 mg, 0.17 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to obtain a pale yellow cloudy solution, to which was then added Fe powder (29 mg, 0.51 mmol) and one drop conc. HCl at room temperature, followed by stirring for 2 hours at the boil under reflux. The reaction mixture was filtered, concentrated and purified using preparative TLC on silica gel using EtOAc / Hx (1/1) to give the title compound as a yellow solid (54 mg, 0.12 mmol, 73%).

¹ H-NMR (300 MHz, CDCl ₃ ) (apparently a mixture of 2 isomers) δ 1.17-1.21 (m, 6H), 2.71 (s, 1H), 2.77 (2H) , 2.78-2.89 (m, 1H), 5.56 (s, broad, 1H), 5.58 (s, 0.6H), 5.75 (s, broad, 0.8H) 6.63 (dd, J = 8.2, 0.5 Hz, 0.6H), 6.71-6.85 (m, 2H), 6.91-6.96 (m, 2H), 7 , 19 (dd, J = 7.4, 0.5 Hz, 0.6H), 7.28-7.32 (m, 1H), 7.48-7.60 (m, 1H), 8.72 (s, 0.4H), 8.75 (d, J = 3.9 Hz, 1H).

<EXAMPLE 207> (4R) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - 2-oxothiazolidine-4-carboxamide

(4R) -N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2-oxothiazolidine-4-carboxamide (100 mg, 0.213 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to obtain a pale yellow cloudy solution, to which was then added Fe powder (36 mg, 0.64 mmol) ) and two drops conc. HCl at room temperature, followed by stirring for 2 hours at the boil under reflux. The reaction mixture was filtered, concentrated, and purified using preparative TLC on silica gel using EtOAc / Hx (1/1) to give the title compound as a yellow solid (47 mg, 0.11 mmol, 50%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.170 (d, J = 6.9 Hz, 3H), 1.173 (d, J = 6.9 Hz, 3H), 2.83 (hept., J = 6.9 Hz, 1H), 3.49-3.78 (m, 2H), 4.46-4.53 (m, 1H), 6.66 (s, 1H), 6.70 (s, br ., 1H), 6.85 (d, br., J = 7.3 Hz, 1H), 7.00 (d, J = 7.1 Hz, 1H), 7.35 (s, br., 1H ), 7.39-7.51 (m, 1H).

<EXAMPLE 208> N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-2-carboxamide

A solution of indole-2-carboxylic acid (130 mg, 0.806 mmol) in anhydrous DCM was stirred together with oxalyl chloride (0.08 ml, 0.967 mmol) and the catalyst at room temperature for 1 hour. The reaction mixture was concentrated to obtain indole-2-acyl chloride. 9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (190 mg, 0.643 mmol), indole-2-acyl chloride (130 mg 0.707 mmol) and triethylamine (0.13 ml, 0.964 mmol) were dissolved in anhydrous DCM (2 ml) and stirred at room temperature for 2 hours. After extraction with DCM and water, the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Separation and purification by silica gel column chromatography (30% ethyl acetate mixed with 20% hexane) gave the title compound. 50 mg (38%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.18 (dd, J = 7.2 Hz, 2.4 Hz, 6H, CH ₃ ) 2.85 (hept., J = 6.9 Hz, 1H , CH) 6.68 (s, 1H, ArH / NH / OH) 6.92 (d, J = 8.1, 1H, ArH) 7.01-7.06 (m, 1H, ArH) 7.19 (d, J = 7.8 Hz, 1H, ArH) 7.22 (s, 1H, ArH) 7.38 (d, J = 8.1 Hz, 1H, ArH) 7.47 (d, J = 8 , 1 Hz, 1H, ArH) 7.59 (d, J = 7.8 Hz, 1H, ArH) 7.74-7.88 (m, 3H, ArH).

<EXAMPLE 209> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-3-carboxamide

Triethylamine (0.35 ml, 2.53 mmol) and indole-3-acyl chloride (330 mg, 0.186 mmol) were added to the solution of 9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1, 2-b] furan-10 (9bH) -one (500 mg, 1.69 mmol) in anhydrous DCM (5 ml), followed by stirring at room temperature for 3 hours. The reaction mixture was extracted with DCM and water, and the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Separation and purification by silica gel column chromatography (30% ethyl acetate mixed with 30% hexane) gave the title compound. 60 mg (9%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (dd, J = 6.8 Hz, J = 2.4 Hz, 6H, CH ₃ ) 2.78 (hept., J = 6.8 Hz , 1H, CH) 6.80 (d, J = 8.1 Hz, 1H, ArH) 7.21 (s, 1H, ArH) 7.37-7.58 (m, 2H, ArH) 7.55- 7.58 (m, 1H, ArH) 7.75 (d, J = 2.7 Hz, 1H, ArH) 7.813-7.850 (m, 2H, ArH) 7.99-8.07 (m, 2H, ArH ) 8.95 (s, 1H, NH / ArH).

<EXAMPLE 210> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide

9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (300 mg, 1.01 mmol) together with 5-nitro-3 -pyrazolecarboxylic acid (175 mg, 1.11 mmol) was dissolved in anhydrous DCM (3 ml), to which EDCI.HCl (290 mg, 1.52 mmol) and HOBt (205 mg, 1.52 mmol) were then added, followed by stirring overnight at room temperature. Then it was extracted with DCM and water, the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Separation and purification by silica gel column chromatography (30% ethyl acetate mixed with 40% hexane) gave the title compound. 150 mg (34%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (dd, J = 6.9 Hz, J = 2.4 Hz, 6H, CH ₃ ) 2.84 (hept., J = 6.9 Hz , 1H, CH) 6.91 (d, J = 8.1 Hz, 1H, ArH) 6.68 (s, 1H, ArH / NH / OH) 7.42 (d, J = 8.1 Hz, 1H , ArH) 7.60 (s, 2H, ArH.) 7.71-7.9 (m, 2H, ArH) 7.9-7.93 (m, H, ArH) 7.93 (s, br. , 1H, ArH).

<EXAMPLE 211> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-phenyl-5- (trifluoromethyl ) -1H-pyrazole-4-carboxamide

9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (200 mg, 0.677 mmol) and 1-H-phenyl-5- (trifluoromethyl) -1H-pyrazole-4-carboxylic acid (190 mg, 0.744 mmol) was dissolved in anhydrous DCM (2 ml), to which EDCI.HCl (190 mg, 1.015 mmol) and HOBt (137 mg, 1.015 mmol) were then added. ) followed by stirring overnight at room temperature. After extraction with DCM and water, the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Separation and purification of the dark brown mixture by silica gel column chromatography (30% ethyl acetate, mixed with 40% hexane) gave the title compound. 50 mg (14%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (dd, J = 6.9 Hz, J = 2.4 Hz, 6H, CH ₃ ) 2.84 (hept., 1H, CH) 6, 68 (s, 1H, ArH / NH / OH) 6.90 (d, J = 8.1 Hz, 1H, ArH) 7.42-7.46 (m, 3H, ArH) 7.54-7.62 (m, 4H, ArH) 7.75-7.90 (m, 2H, ArH) 7.90-8.10 (m, 1H, ArH) 8.10 (s, 1H, ArH / NH).

<EXAMPLE 212> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 1H-indazole-3-carboxamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-indazole- 3-carboxamide (190 mg, 0.39 mmol) was dissolved in ethanol: water (10 ml: 1 ml) and Fe (66 mg, 1.17 mmol) was added, followed by two drops of conc. HCl. The reaction mixture was heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a yellow solid (92 mg, 52%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz, 1H, CH) , 6.67 ~ 6.72 (m, 2H, ArH), 6.88 (dd, J = 7.9 Hz, 1.0 Hz, 1H, ArH), 7.03 (d, J = 7.3 Hz, 1H, ArH), 7.19 (t, J = 7.6 Hz, 1H, ArH), 7.38 (t, J = 7.5 Hz, 1H, ArH), 7.43 ~ 7.57 (m, 3H, ArH), 8.09 (d, J = 8.2 Hz, 1H, ArH).

<EXAMPLE 213> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2- (1H-tetrazol-1-yl) acetamide

N- (4b-Hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H -tetrazol-1-yl) acetamide (200 mg, 0.44 mmol) was dissolved in a solvent ethanol: water (10 ml: 1 ml) and Fe (74 mg, 1.32 mmol) was added, followed by two drops of conc. HCl. The reaction mixture was heated for 3 hours at the boil under reflux. After concentration in vacuo, purification by column chromatography (ethyl acetate: n-hexane = 2: 1) gave the title compound as a yellow solid (104 mg, 56%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (dd, J = 6.9 Hz, 1.2 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz , 1H, CH), 5.36 (m, 2H, CH ₂ ), 6.62 ~ 6.66 (m, 2H, ArH), 6.87 (dd, J = 7.9 Hz, 1.1 Hz , 1H, ArH), 6.96 (d, J = 7.3 Hz, 1H, ArH), 7.38 ~ 7.43 (m, 2H, ArH), 9.11 (s, 1H, ArH).

<EXAMPLE 214> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-3-carboxamide

Iron powder (0.11 g, 1.9 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) quinoline-3-carboxamide (0.13 g, 0.27 mmol) in absolute ethanol (8 ml) and heated for 1 hour under reflux . The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with Et ₃ N-treated silica gel, to give the title compound. 82 mg (65%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80-2.90 (sept., 1H, CH) 6.70- 6.74 (m, 2H, ArH) 6.89 (d, J = 7.8 Hz, 1H, ArH) 7.04 (d, J = 7.2 Hz, 1H, ArH) 7.48 (t, J = 7.2 Hz, 2H, ArH) 7.68 (t, J = 7.2 Hz, 1H, ArH) 7.87 (t, J = 7.8 Hz, 1H, ArH) 8.02-8 08 (m, 2H, ArH) 8.86 (s, 1H, ArH) 9.23 (s, 1H, ArH).

<EXAMPLE 215> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide

Iron powder (0.12 g, 2.20 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinoline-4-carboxamide (0.15 g, 0.30 mmol) in absolute ethanol (10 ml) and heated for 1 hour at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2) filled with silica gel treated with Et ₃ N to give the title compound. 0.12 g (92%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.77-2.86 (sept., 1H, CH) 6.66 ( s, 1H, NH) 6.74-6.87 (m, 2H, ArH) 7.08 (d, J = 7.4 Hz, 1H, ArH) 7.40-7.54 (m, 2H, ArH ) 7.65-7.72 (m, 2H, ArH) 7.81 (t, J = 7.8 Hz, 1H, ArH) 8.06 (d, J = 8.7 Hz, 1H, ArH) 8 40 (d, J = 8.4 Hz, 1H, ArH) 8.90 (d, J = 4.1 Hz, 1H, ArH).

<EXAMPLE 216> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylthiophene 2-carboxamide

Iron powder (0.06 g, 1.24 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5-methylthiophene-2-carboxamide (0.08 g, 0.17 mmol) in absolute ethanol (10 ml) and heated for 1 hour under reflux a refrigerator. The reaction mixture was washed with ethyl acetate and filtered to remove iron powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with Et ₃ N-treated silica gel, to give the title compound. 67 mg (90%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.53 (s, 3H, Me) 2.75-2.84 (sept ., 1H, CH) 6.57 (d, J = 8.1 Hz, 1H, ArH) 6.64-6.71 (m, 2H, ArH) 6.76 (s, 1H, ArH) 6.87 (d, J = 3.0 Hz, 1H, ArH) 7.24 (d, J = 8.1 Hz, 1H, ArH) 7.32 (t, J = 8.1 Hz, 1H, ArH) 7, 68 (d, J = 3.6 Hz, 1H, ArH).

<EXAMPLE 217> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxythiophene 3-carboxamide

Fe powder (0.06 g, 1.24 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-methoxythiophene-3-carboxamide (0.28 g, 0.58 mmol) and heated for 1 hour at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N, and then recrystallized from methylene chloride to give the title compound. 77 mg (29%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.75-2.84 (sept., 1H, CH) 3.89 ( s, 3H, OMe) 6.62-6.69 (m, 3H, ArH) 6.82-6.90 (m, 1H, ArH) 6.96-7.05 (m, 1H, ArH) 7, 38-7.47 (m, 2H, ArH) 7.95 (s, 1H, ArH).

<EXAMPLE 218> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide

A solution of picolinic acid (0.26 g, 2.1 mmol) in anhydrous MeCN (30 ml) was mixed with EDCI (0.45 g, 2.3 mmol) and HOBt (0.25 g, 1.8 mmol) at room temperature for 10 min, and then together with 9b-amino-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one ( 0.52 g, 1.76 mmol) at room temperature for 3 hours. The reaction mixture was diluted in methylene chloride and washed many times with water, the organic layer was dried and filtered. Purification by column chromatography (ethyl acetate: hexane = 1: 4) gave the title compound. 0.53 g (76%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.83 (sept., J = 6.9 Hz, 1H, CH) 5, 69 (s, 1H) 6.75 (s, 1H) 6.83 (d, J = 7.8 Hz, 1H, ArH) 7.36 (d, J = 7.8 Hz, 1H, ArH) 7, 44-7.48 (m, 1H, ArH) 7.55-7.60 (m, 1H, ArH) 7.80-7.86 (m, 3H, ArH) 8.02-8.09 (m, 2H, ArH) 8.60-8.61 (m, 1H, ArH) 9.17 (s, 1H).

<EXAMPLE 219> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrimidine-4-carboxamide

A solution of isonicotinic acid (0.26 g, 2.1 mmol) in anhydrous methylene chloride (20 ml) and dimethylformamide (10 ml) was mixed with EDCI (0.45 g, 2.3 mmol) and HOBt (0.25 g, 1.8 mmol) for 10 min at room temperature, and then together with 9b-amino-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.46 g, 1.56 mmol) for 24 hours at room temperature. The reaction mixture was diluted in methylene chloride and washed many times with water, the organic layer was dried and filtered. Purification by column chromatography (ethyl acetate: hexane = 1: 4) gave the title compound. 0.20 g (32%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.81-2.90 (m, 1H, CH) 6.70 (br s, 1H, ArH) 6.91-6.93 (m, 1H, ArH) 7.42-7.47 (m, 1H, ArH) 7.72-7.82 (m, 6H) 8.66 -8.68 (m, 2H, ArH).

<EXAMPLE 220> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H -tetrazol-5-yl) acetamide

A solution of 1H-tetrazole-5-acetic acid (131 mg, 1.02 mmol) in methylene chloride (20 ml) and DMF (5 ml) was mixed with EDCI (196 mg, 1.02 mmol) and HOBt (138 mg, 1 , 02 mmol) for 20 min, and then together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (20% methanol in methylene chloride) afforded the title compound as a white solid (136 mg, 33%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz, 1H, CH) 3.97 (s, 2H, ArH), 6.66 (s, 1H, ArH), 6.88 (dd, J = 8.0 Hz, 1.1 Hz, 1H, ArH), 7.36 ( d, J = 7.9 Hz, 1H, ArH), 7.68 ~ 7.79 (m, 3H, ArH).

<EXAMPLE 221> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [ d] [1,2,3] triazole-5-carboxamide

A solution of benzotriazole-5-carboxylic acid (166 mg, 1.02 mmol) in methylene chloride (20 ml) and DMF (5 ml) was reacted with EDCI (196 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min, and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1 , 02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 2: 1) afforded N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2 -b] furan-9b-yl) -1H-benzo [d] [1,2,3] triazole-5-carboxamide as a white solid (210 mg, 47%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.9 Hz, 1H, CH) , 6.69 (d, J = 1.2 Hz, 1H, ArH), 6.91 (dd, J = 7.9 Hz, 1.2 Hz, 1H, ArH), 7.48 (d, J = 7.9 Hz, 1H, ArH), 7.62 (m, 1H, ArH), 7.79 ~ 7.97 (m, 5H, ArH), 8.49 (s, 1H, ArH).

<EXAMPLE 222> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-1, 2,4-triazole-3-carboxamide

1,2,4-Triazole-3-carboxylic acid (116 mg, 1.02 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml) and reacted with EDCI (196 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 minutes and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10 -one (300 mg, 1.02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (10% methanol in methylene chloride) afforded the title compound as a white solid. (141 mg, 35%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.9 Hz, 1H, CH) 6.68 (s, 1H, ArH), 6.90 (d, J = 8.0 Hz, 1H, ArH), 7.45 (d, J = 7.9 Hz, 1H, ArH), 7, 60 ~ 7.97 (m, 4H, ArH); 8.40 (s, 1H, ArH).

<EXAMPLE 223> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5-nitrothiophene 2-carboxamide

5-Nitrothiophene-2-carboxylic acid (212 mg, 1.22 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml) and reacted with EDCI (234 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) for 20 min, and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.22 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2 -b] furan-9b-yl) -5-nitrothiophene-2-carboxamide as a yellow solid (80 mg, 17%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz, 1H, CH) 6.67 (s, 1H, ArH), 6.90 (d, J = 7.9 Hz, 1H, ArH), 7.43 (d, J = 7.9 Hz, 1H, ArH), 7, 71 ~ 7.73 (m, 2H, ArH); 7.73 ~ 7.93 (m, 4H, ArH).

<EXAMPLE 224> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2,6- dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamide

Orotic acid (190 mg, 1.22 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), reacted with EDCI (233 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) in for 20 minutes, and then stirred with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol ) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (10% methanol in methylene chloride) afforded N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan -9b-yl) -2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-carboxamide as a white solid (91 mg, 21%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz, 1H, CH) , 6.30 (s, 1H, ArH), 6.67 (s, 1H, ArH), 6.90 (d, J = 8.0 Hz, 1H, ArH), 7.39 (d, J = 7 8 Hz, 1H, ArH), 7.60 ~ 7.93 (m, 4H, ArH).

<EXAMPLE 225> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo- 2H-chromene-3-carboxamide

Coumarin-3-carboxylic acid (232 mg, 1.22 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), the reaction was carried out with EDCI (234 mg, 1.22 mmol) and HOBt (165 mg, 1, 22 mmol) for 20 minutes and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a white solid (377 mg, 79%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.86 (sept., J = 6.9 Hz, 1H, CH) 6.70 (s, 1H, ArH), 6.92 (d, J = 7.9 Hz, 1H, ArH), 7.41 ~ 7.45 (m, 3H, ArH), 7.72 ~ 7 81 (m, 4H, ArH), 7.88 ~ 7.89 (m, 2H, ArH), 8.74 (s, 1H, ArH).

<EXAMPLE 226> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo- 2H-pyran-5-carboxamide

Coumaric acid (171 mg, 1.22 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), reacted with EDCI (234 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) in for 20 min, and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol ) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a yellow solid (60 mg, 14%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (dd, J = 6.9 Hz, 2.8 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.9 Hz , 1H, CH), 5.61 (d, J = 9.3 Hz, 1H, ArH), 6.78 (s, 1H, ArH), 6.93 (dd, J = 7.9 Hz, 1, 0 Hz, 1H, ArH), 7.44 (d, J = 7.9 Hz, 1H, ArH), 7.49 (d, J = 9.3 Hz, 1H, ArH), 7.63 (t, J = 7.4 Hz, 1H, ArH), 7.81 (d, J = 7.7 Hz, 1H, ArH), 7.87 ~ 7.92 (m, 2H, ArH), 8.01 (d , J = 7.8 Hz, 1H, ArH).

<EXAMPLE 227> N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [ d] imidazole-2-carboxamide

1H-Benzimidazole-2-carboxylic acid (183 mg, 1.02 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), the reaction was carried out for 20 min with EDCI (195 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) and stirred at room temperature overnight with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10 -one (250 mg, 0.85 mmol). After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2 -b] furan-9b-yl) -1H-benzo [d] imidazole-2-carboxamide as a white solid (210 mg, 56%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.86 (sept., J = 6.9 Hz, 1H, CH) 6.69 (s, 1H, ArH), 6.93 (dd, J = 7.9 Hz, 1.2 Hz, 1H, ArH), 7.32 ~ 7.35 (m, 2H, ArH), 7.49 (d, J = 7.9 Hz, 1H, ArH), 7.63 ~ 7.64 (m, 4H, ArH), 7.89 ~ 7.91 (m, 2H, ArH).

<EXAMPLE 228> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (2 -chloro-6-fluorophenyl) -5-methylisoxazole-4-carboxamide

5- (2-Chloro-6-fluorophenyl) -N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b ] furan-9b-yl) -2-methylcyclopenta-1,4-dialkarboxamide (100 mg, 0.173 mmol) was added to 5 ml EtOH: H ₂ O (10: 1) to obtain a pale yellow cloudy solution, to which was then added Fe powder (41 mg, 0.73 mmol) and three drops conc. HCl at room temperature, followed by stirring for 2 hours at the boil under reflux. The reaction mixture was filtered, concentrated and purified using preparative TLC on silica gel using EtOAc / Hx (1/1) to give the title compound as a yellow solid (26.7 mg, 0.487 mmol, 28%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 3H), 1.17 (d, J = 6.8 Hz, 3H), 2.72 (s , 3H), 2.73-2.88 (m, 1H), 6.62 (s, 1H), 6.63-6.82 (m, 2H), 6.93-7.17 (m, 2H ), 7.19-7.25 (m, 1H), 7.39-7.52 (m, 3H).

<EXAMPLE 229> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-phenyl-1H-pyrazol- 5-carboxamide

3-Phenyl-1H-pyrazole-5-carboxylic acid (116 mg, 0.616 mmol) together with HOBt (316 mg, 2.34 mmol) and EDCI.HCl (441 mg, 2.30 mmol) were dissolved in CH ₂ Cl ₂ (10 ml), to which was then added a solution of 9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 mg, 1, 69 mmol) in CH ₂ Cl ₂ (5 ml), followed by stirring at room temperature for 2 hours. The resulting yellow reaction mixture was mixed with water and then extracted twice with CH ₂ Cl ₂ . The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography using EtOAc / Hx (1 / 3-1 / 2) to give the title compound as a white solid (144.7 mg, 0.311 mmol, 50%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.13-1.23 (m, 6H), 2.77-2.92 (m, 1H), 6.68 (s, 1H), 6, 90 (d, J = 7.9 Hz, 1H), 6.93-7.09 (m, 2H), 7.31-7.52 (m, 4H), 7.52-8.07 (m, 6H).

<EXAMPLE 230> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide

EDCI (0.48 g, 2.53 mmol), 9b-amino-4b-hydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - he (0.50 g, 1.46 mmol) and HOBt (0.34 g, 2.53 mmol) were added at 0 ° C in this order to a solution of nicotinic acid (0.31 g, 2.53 mmol) in anhydrous THF (10 ml) and DMF (3 ml), followed by stirring at room temperature for 2 days. During the reaction, the solids were washed with THF and water, filtered and dried to give the title compound. 0.33 g (49%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.14 (d, J = 6.3 Hz, 6H, CH ₃ ) 2.71-2.82 (sept., 1H, CH) 6.67 (s , 1H, NH) 6.80 (d, J = 7.5 Hz, 1H, ArH) 7.30 (t, J = 6.0 Hz, 1H, ArH) 7.38 (d, J = 7.8 Hz, 1H, ArH) 7.53 (t, J = 7.2 Hz, 1H, ArH) 7.63 (s, 1H, ArH) 7.73-7.82 (m, 2H, ArH) 7.91 (s, 1H, OH) 7.97 (d, J = 7.8 Hz, 1H, ArH) 8.10 (d, J = 7.2 Hz, 1H, ArH) 8.56 (d, J = 3 9 Hz, 1H, ArH) 8.96 (s, 1H, ArH).

<EXAMPLE 231> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-oxo- 2- (thiophen-2-yl) acetamide

Fe powder (0.30 g, 5.47 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) thiophene-2-carboxamide (0.36 g, 0.75 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was concentrated in vacuo and purified for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 4) filled with Et ₃ N-treated silica gel to give the title compound. 0.28 g (83%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.81-2.86 (sept., 1H, CH) 6.61- 6.72 (m, 2H, ArH) 6.88 (d, J = 7.5 Hz, 1H, ArH) 7.01 (d, J = 7.2 Hz, 1H, ArH) 7.20 (t, J = 5.1 Hz, 1H, ArH) 7.40 (d, J = 7.5 Hz, 1H, ArH) 7.46 (t, J = 7.8 Hz, 1H, ArH) 7.96 (d , J = 4.5 Hz, 1H, ArH) 8.25 (d, J = 2.7 Hz, 1H, ArH).

<EXAMPLE 232> 5-amino-N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan -2-carboxamide

Fe powder (0.32 g, 5.78 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of 5-amino-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH- benzo [d] indeno [1,2-b] furan-9b-yl) furan-2-carboxamide (0.38 g, 0.79 mmol) in absolute ethanol (10 ml) and heated for 2 hours while boiling with reflux condenser. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was concentrated in vacuo and purified by column chromatography (ethyl acetate: hexane = 1: 4) filled with Et ₃ N-treated silica gel to give the title compound. 61 mg (48%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.25 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.84-2.86 (sept., 1H, CH) 6.75 ( s, 1H, ArH) 6.88-6.94 (m, 2H, ArH) 7.08-7.11 (m, 1H, ArH) 7.25 (t, J = 7.5 Hz, 1H, ArH ) 7.34-7.38 (m, 1H, ArH); 7.38-7.50 (m, 2H, ArH).

<EXAMPLE 233> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole- 2-carboxamide

Fe powder (0.09 g, 1.6 mmol), conc. HCl (0.03 ml) and water (0.8 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [ d] indeno [1,2-b] furan-9b-yl) -1H-pyrrole-2-carboxamide (0.10 g, 0.23 mmol) in ethanol (8 ml) and heated for 2 hours while boiling with reflux condenser. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2) filled with silica gel treated with Et ₃ N to give the title compound. 90 mg (96%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.82-2.86 (sept., 1H, CH) 6.16 ( d, J = 2.7 Hz, 1H, ArH) 6.88 (s, 1H, ArH) 6.70-6.74 (m, 1H, ArH) 6.85-6.90 (m, 3H, ArH ) 7.03 (d, J = 5.1 Hz, 1H, ArH) 7.30-7.46 (m, 2H, ArH).

<EXAMPLE 234> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxyisonicotinamide

Powder Fe (0.12 g, 2.30 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-methoxyisonicotinamide (0.15 g, 0.31 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was concentrated in vacuo and purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with Et ₃ N-treated silica gel, to give the title compound. 0.10 g (71%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.78-2.87 (sept., 1H, CH) 3.91 ( s, 3H, OMe) 6.67 (s, 1H, ArH) 6.74 (m, 1H, ArH) 6.85 (d, J = 8.1 Hz, 1H, ArH) 7.02 (d, J = 7.2 Hz, 1H, ArH) 7.19 (s, 1H, ArH) 7.29 (d, J = 5.4 Hz, 1H, ArH) 7.39-7.48 (m, 2H, ArH ) 8.20 (d, J = 4.8 Hz, 1H, ArH).

<EXAMPLE 235> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b] thiophene-2-carboxamide

Fe (50 mg, 0.90 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b] thiophene-2-carboxamide (150 mg, 0.30 mmol) in a solvent ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 3) gave the title compound as a yellow solid (76 mg, 54%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.19 (dd, J = 6.9 Hz, 1.2 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.9 Hz , 1H, CH), 6.67 ~ 6.70 (m, 2H, ArH), 6.90 (d, J = 7.8 Hz, 1H, ArH), 7.01 (d, J = 7.3 Hz, 1H, ArH), 7.39 ~ 7.48 (m, 4H, ArH), 7.87 (d, J = 7.5 Hz, 1H, ArH), 8.10 (s, 1H, ArH) .

<EXAMPLE 236> 3- (2,6-Dichlorophenyl) -N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan -9b-yl) -5-methylisoxazole-4-carboxamide

A solution of 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1.02 mmol) in methylene chloride (20 ml) was stirred overnight with 3- (2,6-dichlorophenyl) -5-methyl-4-isoxazolecarbonyl chloride (355 mg, 1.22 mmol) and triethylamine (0.3 ml, 1.83 mmol) at room temperature. After completion of the reaction, concentration in vacuo and purification by column chromatography (ethyl acetate: n-hexane = 1: 3) gave the title compound (109 mg, 19%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.14 (dd, J = 6.8 Hz, 6H, CH ₃ ), 2.75 (s, 3H, CH ₃ ), 2.78 (sept., J = 6.8 Hz, 1H, CH), 6.02 (s, 1H), 6.56 (s, 1H), 6.680 (s, 1H, ArH), 6.75 (d, J = 7.8 Hz, 1H, ArH), 6.88 (d, J = 7.8 Hz, 1H, ArH), 7.48 (t, J = 7.5 Hz, 1H, ArH), 7.51 ~ 7.68 (m, 4H, ArH), 7.76 (t, J = 7.5 Hz, 1H, ArH), 7.98 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 237> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 9H-xanthene-9-carboxamide

Fe (37 mg, 0.66 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -9H-xanthene-9-carboxamide (120 mg, 0.22 mmol) in a solvent ethanol: water (10 ml: 1 ml) and heated for 1.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a yellow solid (65 mg, 57%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (dd, J = 6.9 Hz, 2.3 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.9 Hz , 1H, CH), 5.09 (s, 1H, CH), 6.59 (s, 1H, ArH), 6.66 (s, 1H, ArH), 6.88-6.94 (m, 2H , ArH), 7.01-7.06 (m, 3H, ArH), 7.15 (m, 1H, ArH), 7.22 (m, 1H, ArH), 7.28 (t, J = 7 , 3 Hz, 1H, ArH), 7.36 (m, 1H, ArH), 7.42-7.45 (m, 2H, ArH), 7.54 (m, 1H, ArH).

<EXAMPLE 238> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnoline -4-carboxamide

Fe (85 mg, 1.51 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnoline-4-carboxamide (250 mg, 0.50 mmol) in a solvent ethanol: water (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a yellow solid (230 mg, 99%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.82 (sept., J = 6.9 Hz, 1H, CH) 6.68 (s, 1H, ArH), 6.72 (d, J = 8.1 Hz, 1H, ArH), 6.86 (d, J = 8.1 Hz, 1H, ArH), 7, 07 (d, J = 7.1 Hz, 1H, ArH), 7.44-7.51 (m, 2H, ArH), 7.90 ~ 8.01 (m, 2H, ArH), 8.44- 8.51 (m, 2H, ArH); 9.46 (s, 1H, ArH).

<EXAMPLE 239> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4-carboxamide

A solution of cinnolin-4-carboxylic acid (183 mg, 1.02 mmol) in methylene chloride (20 ml) was reacted with EDCI (195 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min and then stirred overnight with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (250 mg, 0.85 mmol ) at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a white solid (290 mg, 63%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.82 (sept., J = 6.8 Hz, 1H, CH) 6.69 (s, 1H, ArH), 6.89 (d, J = 7.8 Hz, 1H, ArH), 7.45 (d, J = 7.9 Hz, 1H, ArH), 7, 65 (m, 1H, ArH), 7.85-8.03 (m, 5H, ArH), 8.42 (d, J = 8.0 Hz, 1H, ArH), 8.51 (d, J = 8.4 Hz, 1H, ArH); 9.45 (s, 1H, ArH).

<EXAMPLE 240> N- (4b-Hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [ d] imidazole-5-carboxamide

5-Benzimidazolecarboxylic acid (198 mg, 1.22 mmol) was dissolved in methylene chloride (20 ml) and DMF (3 ml), and EDCI (233 mg, 1.22 mmol) and HOBt (165 mg, 1.22 mmol) were reacted. ) for 20 min, and then stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one (300 mg, 1, 02 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (MC in MeOH 10%) afforded the title compound as a white solid (207 mg, 46%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.8 Hz, 1H, CH) 6.68 (s, 1H, ArH), 6.92 (d, J = 7.8 Hz, 1H, ArH), 7.49 (d, J = 8.1 Hz, 1H, ArH), 7, 61 ~ 7.64 (m, 2H, ArH), 7.78 ~ 7.83 (m, 3H, ArH), 7.96 (d, J = 7.5 Hz, 1H, ArH), 8.19 ( s, 1H, ArH), 8.26 (s, 1H, ArH).

<EXAMPLE 241> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridine -9-carboxamide

Fe (46 mg, 0.82 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridine-9-carboxamide (150 mg, 0.27 mmol) in a solvent ethanol: water (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 1) gave the title compound as a yellow solid (90 mg, 65%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.14 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.80 (sept., J = 6.9 Hz, 1H, CH) 6.67 (s, 1H, ArH), 6.74 (d, J = 7.4 Hz, 1H, ArH), 6.81 (d, J = 7.5 Hz, 1H, ArH), 7, 13 (d, J = 6.8 Hz, 1H, ArH), 7.42 (d, J = 7.0 Hz, 1H, ArH), 7.51 (t, J = 7.5 Hz, 1H, ArH ), 7.62 (t, J = 7.1 Hz, 1H, ArH), 7.80 (t, J = 7.0 Hz, 1H, ArH), 7.84 (t, J = 6.8 Hz , 1H, ArH), 8.13-8.18 (m, 2H, ArH), 8.56 (d, J = 7.5 Hz, 1H, ArH), 8.72 (d, J = 7.5 Hz, 1H, ArH).

<EXAMPLE 242> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4-nitro-1H-pyrazole-3-carboxamide

Fe (76 mg, 1.36 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4-nitro-1H-pyrazole-3-carboxamide (217 mg, 0.45 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (methanol in methylene chloride 5%) afforded the title compound as a yellow solid (134 mg, 71%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.8 Hz, 1H, CH) 6.66-6.68 (m, 2H, ArH), 6.87-6.89 (m, 1H, ArH), 7.01-7.03 (m, 1H, ArH), 7.44- 7.48 (m, 2H, ArH); 8.48 (s, 1H, ArH).

<EXAMPLE 243> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4-methylpicolinamide

Fe (109 mg, 1.96 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4-methylpicolinamide (300 mg, 0.65 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 3) gave the title compound as a yellow solid (113 mg, 40%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.14 (d, J = 6.7 Hz, 6H, CH ₃ ), 2.35 (s, 3H, CH ₃ ), 2.79 (sept. , J = 6.7 Hz, 1H, CH), 6.65 ~ 6.66 (m, 2H, ArH), 6.83 (d, J = 5.9 Hz, 1H, ArH), 7.03 ( d, J = 6.2 Hz, 1H, ArH), 7.30 (d, J = 4.1 Hz, 1H, ArH), 7.42 ~ 7.45 (m, 2H, ArH), 7.78 (d, 1H, ArH), 8.40 (d, J = 4.6 Hz, 1H, ArH).

<EXAMPLE 244> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4- (trifluoromethyl) picolinamide

Fe (104 mg, 1.87 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- (trifluoromethyl) picolinamide (320 mg, 0.62 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 4 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a yellow solid (127 mg, 42%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.79 (sept., J = 6.8 Hz, 1H, CH) , 6.65 ~ 6.75 (m, 2H, ArH), 6.85 (d, J = 6.7 Hz, 1H, ArH), 7.03 (d, J = 6.7 Hz, 1H, ArH ), 7.43 ~ 7.51 (m, 2H, ArH), 7.81 (d, J = 4.6 Hz, 1H, ArH), 8.20 (s, 1H, ArH), 8.82 ( d, J = 4.6 Hz, 1H, ArH).

<EXAMPLE 245> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 5-cyanopicolinamide

Fe (107 mg, 1.91 mmol) and 2 drops conc. HCl was successively added to a solution of 5-cyano-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 9b-yl) picolinamide (300 mg, 0.64 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 4 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a yellow solid (40 mg, 14%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.8 Hz, 1H, CH) , 6.68 ~ 6.73 (m, 2H, ArH), 6.86 (d, J = 7.3 Hz, 1H, ArH), 7.02 (d, J = 6.8 Hz, 1H, ArH ), 8.11 (d, J = 8.1 Hz, 1H, ArH), 8.31 (d, J = 8.1 Hz, 1H, ArH), 8.92 (s, 1H, ArH).

<EXAMPLE 246> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-chloropicolinamide

Fe (157 mg, 2.81 mmol) and 2 drops conc. HCl was successively added to a solution of 3-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 9b-yl) picolinamide (450 mg, 0.94 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 2) gave the title compound as a yellow solid (168 mg, 40%).

¹ H-NMR (500 MHz, CD ₃ OD) δ 1.18 (dd, J = 6.9 Hz, 2.2 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.9 Hz , 1H, CH), 6.67 (m, 2H, ArH), 6.85 ~ 6.86 (m, 1H, ArH), 7.02 ~ 7.03 (m, 1H, ArH), 7.44 ~ 7.51 (m, 3H, ArH), 7.93 (dd, J = 8.1 Hz, 1.1 Hz, 1H, ArH), 8.51 (d, J = 4.1 Hz, 1H, ArH).

<EXAMPLE 247> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 4-methoxyquinoline-2-carboxamide

Fe (140 mg, 2.51 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4-methoxyquinoline-2-carboxamide (440 mg, 0.84 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (ethyl acetate: n-hexane = 1: 3) gave the title compound as a yellow solid (52 mg, 12%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.22 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.87 (sept., J = 6.9 Hz, 1H, CH) 4.11 (s, 3H, OCH ₃ ), 6.72 ~ 6.74 (m, 2H, ArH), 6.90 ~ 6.93 (m, 1H, ArH), 7.03 ~ 7.06 (m, 1H, ArH), 7.45 ~ 7.55 (m, 3H, ArH), 7.61 (t, J = 7.8 Hz, 1H, ArH), 7.77 (t, J = 7 8 Hz, 1H, ArH), 8.05 (d, J = 8.1 Hz, 1H, ArH), 8.24 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 248> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isoquinoline-3-carboxamide

Fe powder (0.16 g, 2.92 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinoline-3-carboxamide (0.20 g, 0.40 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered. This filtrate was purified for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 4), filled with Et ₃ N-treated silica gel, to give the title compound. 90 mg (50%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.20 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.81-2.88 (sept., 1H, CH) 6.70- 6.80 (m, 2H, ArH) 6.85-6.90 (m, 1H, ArH) 7.07-7.10 (m, 1H, ArH) 7.45-7.52 (m, 2H, ArH) 7.77-7.87 (m, 2H, ArH) 8.05 (d, J = 7.5 Hz, 1H, ArH) 8.17 (d, J = 8.1 Hz, 1H, ArH) 8.43 (s, 1H, ArH); 9.27 (s, 1H, ArH).

<EXAMPLE 249> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methylisonicotinamide

Fe powder (0.17 g, 3.17 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-methylisonicotinamide (0.20 g, 0.43 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered. The filtrate was purified for 30 min by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 0.13 g (72%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.56 (s, 3H, CH ₃ ) 6.67-6.70 ( m, 2H, ArH) 6.87 (d, J = 6.9 Hz, 1H, ArH) 7.01 (d, J = 6.3 Hz, 1H, ArH) 7.42-7.44 (m, 2H, ArH) 7.58 (d, J = 5.1 Hz, 1H, ArH) 7.67 (s, 1H, ArH) 8.49 (d, J = 5.1 Hz, 1H, ArH).

<EXAMPLE 250> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-fluoroisonicotinamide

Fe powder (0.26 g, 4.72 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of 3-fluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH- benzo [d] indeno [1,2-b] furan-9b-yl) isonicotinamide (0.30 g, 0.64 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes using column chromatography (ethyl acetate: hexane = 1: 2) filled with silica gel treated with Et ₃ N to give the title compound. 0.16 g (84%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80-2.84 (m, 1H, CH) 6.67-6 72 (m, 2H, ArH) 6.86 (d, J = 5.7 Hz, 1H, ArH) 7.02 (d, J = 6.3 Hz, 1H, ArH) 7.43-7.46 (m, 2H, ArH) 7.66 (t, J = 5.1 Hz, 1H, ArH) 8.46 (d, J = 4.5 Hz, 1H, ArH) 8.56 (s, 1H, ArH )

<EXAMPLE 251> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloroisonicotinamide

Fe powder (0.16 g, 3.04 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of 3-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH- benzo [d] indeno [1,2-b] furan-9b-yl) isonicotinamide (0.20 g, 0.41 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 0.15 g (83%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.77-2.86 (m, 1H, CH) 6.66-6 71 (m, 2H, NH, ArH) 6.84 (d, J = 7.5 Hz, 1H, ArH) 7.03 (d, J = 6.9 Hz, 1H, ArH) 7.41-7 , 49 (m, 2H, ArH) 7.57 (d, J = 4.8 Hz, 1H, ArH) 8.52 (d, J = 4.8 Hz, 1H, ArH) 8.62 (s, 1H , ArH).

<EXAMPLE 252> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl- 1H-imidazole-2-carboxamide

Fe powder (0.10 g, 1.95 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1-methyl-1H-imidazole-2-carboxamide (0.12 g, 0.26 mmol) in absolute ethanol (10 ml) and heated for 2 hours when boiling under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 20 mg (18%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.79-2.87 (m, 1H, CH) 3.89 (m , 3H, CH ₃ ) 6.67 (s, 1H, ArH) 6.73 (d, J = 6.3 Hz, 1H, ArH) 6.86 (d, J = 7.1 Hz, 1H, ArH) 7.00-7.02 (m, 2H, ArH); 7.20 (s, 1H, ArH); 7.39-7.48 (m, 2H, ArH).

<EXAMPLE 253> 2 - ((1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1 -oxide

Fe (109 mg, 1.95 mmol) and 2 drops conc. HCl was successively added to a solution of 2 - ((4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1-oxide (300 mg, 0.65 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After concentration in vacuo, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid (110 mg, 39%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.9 Hz, 1H, CH) 6.68-6.76 (m, 2H, ArH), 6.87 (d, J = 7.4 Hz, 1H, ArH), 7.02 (d, J = 7.2 Hz, 1H, ArH ), 7.39-7.50 (m, 2H, ArH), 7.62-7.64 (m, 2H, ArH), 8.20-8.23 (m, 1H, ArH), 8.39 -8.40 (m, 1H, ArH).

<EXAMPLE 254> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chloronicotinamide

Fe (24 mg, 0.44 mmol) and 2 drops conc. HCl was successively added to a solution of 4-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide (70 mg, 0.15 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (10% MeOH in CH ₂ Cl ₂ ) afforded the title compound as a yellow solid (50 mg, 74%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.83 (sept., J = 6.8 Hz, 1H, CH) 6.56 (d, J = 7.2 Hz, 1H, ArH), 6.66-6.68 (m, 2H, ArH), 6.86 (d, J = 7.7 Hz, 1H, ArH ), 7.00 (d, J = 7.1 Hz, 1H, ArH), 7.40 ~ 7.46 (m, 2H, ArH), 7.77 (d, J = 7.1 Hz, 1H, ArH), 8.40 (s, 1H, ArH).

<EXAMPLE 255> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoronicotinamide

Fe (72 mg, 1.29 mmol) and 2 drops conc. HCl was successively added to a solution of 5-fluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide (200 mg, 0.43 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 4 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid (50 mg, 27%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.8 Hz, 1H, CH) 6.67-6.71 (m, 2H, ArH), 6.88 (d, J = 7.9 Hz, 1H, ArH), 7.01 (d, J = 7.3 Hz, 1H, ArH ), 7.42 ~ 7.45 (m, 2H, ArH), 8.03 (d, J = 8.7 Hz, 1H, ArH), 8.60 (s, 1H, ArH), 8.86 ( s, 1H, ArH).

<EXAMPLE 256> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-hydroxynicotinamide

Solution of 5-hydroxy-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide (50 mg , 0.11 mmol) in methanol (5 ml) was mixed with 20% of the mass. ammonium sulfide (0.2 ml) and heated for 3.5 hours at the boil under reflux. After removing the solvent, the reaction mixture was extracted with CH ₂ Cl ₂ , dehydrated with Na ₂ SO ₄ , filtered and concentrated. Purification by column chromatography (3% MeOH in CH ₂ Cl ₂ ) afforded the title compound as a yellow solid (168 mg, 40%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.8 Hz, 1H, CH) 6.66-6.71 (m, 2H, ArH), 6.88 (d, J = 7.9 Hz, 1H, ArH), 7.00 (d, J = 7.5 Hz, 1H, ArH ), 8.05 (br., 1H, ArH), 8.24 (br., 1H, ArH).

<EXAMPLE 257> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-hydroxypicolinamide

Solution of 3-hydroxy-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide (190 mg , 0.41 mmol) in methanol (5 ml) was mixed with 20% of the mass. ammonium sulfide (0.2 ml) and heated for 2 hours at the boil under reflux. After removing the solvent, the reaction mixture was extracted with CH ₂ Cl ₂ , dehydrated with Na ₂ SO ₄ , filtered and concentrated. Purification by column chromatography (EtOAc: hexane = 1: 1) gave the title compound as a yellow solid (47 mg, 27%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.79 (sept., J = 6.9 Hz, 1H, CH) 6.50 ~ 6.74 (m, 2H, ArH), 6.80 (d, J = 7.8 Hz, 1H, ArH), 7.00-7.02 (m, 1H, ArH), 7 33-7.55 (m, 2H, ArH).

<EXAMPLE 258> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylnicotinamide

Fe powder (0.17 g, 3.17 mmol), conc. HCl (0.01 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -4-methylnicotinamide (0.20 g, 0.43 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to give the title compound. 0.11 g (53%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.49 (s, 3H, CH ₃ ) 2.77-2.87 ( sept., 1H, CH) 6.66-6.80 (m, 2H, ArH) 6.85 (d, J = 7.5 Hz, 1H, ArH) 7.04 (d, J = 6.9 Hz , 1H, ArH) 7.32 (d, J = 5.1 Hz, 1H, ArH) 7.44-7.49 (m, 2H, ArH) 8.41 (d, J = 5.4 Hz, 1H , ArH) 8.63 (s, 1H, ArH).

<EXAMPLE 259> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylnicotinamide

Fe powder (0.23 g, 4.28 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -5-methylnicotinamide (0.27 g, 0.58 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to give the title compound. 0.13 g (52%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.37 (s, 3H, CH ₃ ) 2.78-2.87 ( sept., 1H, CH) 6.67-6.74 (m, 2H, ArH) 6.86 (d, J = 7.8 Hz, 1H, ArH) 7.03 (d, J = 7.2 Hz , 1H, ArH) 7.40-7.48 (m, 2H, ArH) 8.07 (s, 1H, ArH) 8.49 (s, 1H, ArH) 8.79 (s, 1H, ArH).

<EXAMPLE 260> N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide

Fe powder (0.15 g, 2.70 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7,8-dimethyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) nicotinamide (0.15 g, 0.34 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux.

The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 2: 1), filled with silica gel treated with Et ₃ N to give the title compound. 70 mg (50%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.56 (s, 3H, CH ₃ ) 6.67-6.70 ( m, 2H, ArH) 6.87 (d, J = 6.9 Hz, 1H, ArH) 7.01 (d, J = 6.3 Hz, 1H, ArH) 7.42-7.44 (m, 2H, ArH) 7.58 (d, J = 5.1 Hz, 1H, ArH) 7.67 (s, 1H, ArH) 8.49 (d, J = 5.1 Hz, 1H, ArH).

<EXAMPLE 261> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methoxynicotinamide

Powder Fe (0.12 g, 2.30 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -5-methoxynicotinamide (0.15 g, 0.31 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N to give the title compound. 80 mg (57%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.81-2.86 (sept., 1H, CH) 3.89 ( s, 3H, OMe) 6.67-6.70 (m, 2H, ArH) 6.88 (d, J = 7.2 Hz, 1H, ArH) 7.01 (d, J = 6.6 Hz, 1H, ArH) 7.43-7.45 (m, 2H, ArH) 7.82 (s, 1H, ArH) 8.34 (s, 1H, ArH) 8.58 (s, 1H, ArH).

<EXAMPLE 262> N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinolin-6 carboxamide

Fe powder (0.16 g, 3.03 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7,8-dimethyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide (0.20 g, 0.41 mmol) in absolute ethanol (10 ml) and was heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 2: 1), filled with silica gel treated with Et ₃ N to give the title compound. 0.16 g (86%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 2.22 (d, J = 8.4 Hz, 6H, CH ₃ ) 6.61 (s, 1H, ArH) 6.70 (d, J = 8 , 1 Hz, 1H, ArH) 7.01 (d, J = 6.6 Hz, 1H, ArH) 7.34 (s, 1H, ArH) 7.46-7.48 (m, 1H, ArH) 7 78-7.79 (m, 1H, ArH) 8.10-8.14 (m, 1H, ArH) 8.20-8.28 (m, 1H, ArH) 8.62 (s, 1H, ArH ) 8.74 (d, J = 6.9 Hz, 1H, ArH).

<EXAMPLE 263> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinoline -2-carboxamide

Fe (135 mg, 2.42 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinoline-2-carboxamide (400 mg, 0.81 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 1.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 2) gave the title compound as a yellow solid (132 mg, 35%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.21 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.87 (sept., J = 6.8 Hz, 1H, CH) 6.70-6.73 (m, 2H, ArH), 6.92 (d, J = 7.9 Hz, 1H, ArH), 7.03 (d, J = 7.3 Hz, 1H, ArH ), 7.44-7.51 (m, 2H, ArH), 7.66 (t, J = 7.6 Hz, 1H, ArH), 7.80 (t, J = 7.3 Hz, 1H, ArH), 7.97 (d, J = 8.1 Hz, 1H, ArH), 8.07-8.13 (m, 2H, ArH), 8.44 (d, J = 8.4 Hz, 1H , ArH).

<EXAMPLE 264> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-bromobenzo [b] thiophene-2-carboxamide

Fe (87 mg, 1.56 mmol) and 2 drops conc. HCl was successively added to a solution of 3-bromo-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 9b-yl) benzo [b] thiophene-2-carboxamide (250 mg, 0.52 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 4) gave the title compound as a yellow solid (130 mg, 46%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.9 Hz, 1H, CH) 6.66-6.80 (m, 2H, ArH), 6.89-6.92 (m, 1H, ArH), 7.01-7.05 (m, 1H, ArH), 7.46- 7.55 (m, 4H, ArH); 7.88-7.93 (m, 2H, ArH).

<EXAMPLE 265> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 1H-indole-2-carboxamide

Fe (35 mg, 0.62 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-indole-2-carboxamide (100 mg, 0.21 mmol) in a solvent ethanol: H ₂ O (15 ml: 1 ml) and heated for 4 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 3) gave the title compound as a yellow solid (80 mg, 84%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.84 (sept., J = 6.8 Hz, 1H, CH) 6.69-6.80 (m, 2H, ArH), 6.88 (d, J = 8.1 Hz, 1H, ArH), 7.02-7.07 (m, 2H, ArH), 7 18-7.23 (m, 2H, ArH), 7.37-7.50 (m, 3H, ArH), 7.59 (d, J = 8.0 Hz, 1H, ArH).

<EXAMPLE 266> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinoline -1-carboxamide

Fe (68 mg, 1.21 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinoline-1-carboxamide (200 mg, 0.40 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 3.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 4) gave the title compound as a yellow solid (155 mg, 81%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.14 (dd, J = 6.9 Hz, 1.5 Hz, 6H, CH ₃ ), 2.80 (sept., J = 6.9 Hz , 1H, CH), 6.67 (s, 1H, ArH), 6.70 (d, J = 8.3 Hz, 1H, ArH), 6.85 (dd, J = 8.0 Hz, 1, 0 Hz, 1H, ArH), 7.05 (d, J = 7.1 Hz, 1H, ArH), 7.43-7.50 (m, 2H, ArH), 7.64 (t, J = 7 5 Hz, 1H, ArH), 7.73 (t, J = 8.0 Hz, 1H, ArH), 7.87-7.92 (m, 2H, ArH), 8.44 (d, J = 5.6 Hz, 1H, ArH), 8.94 (d, J = 8.4 Hz, 1H, ArH).

<EXAMPLE 267> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -6-fluoro- 4-methoxyquinoline-3-carboxamide

Fe powder (46.2 mg, 0.82 mmol) and 5 drops conc. HCl was successively added to a solution of 6-fluoro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan- 9b-yl) -4-methoxyquinoline-3-carboxamide (0.15 g, 0.28 mmol) in a solvent ethanol: water (10: 1, 10 ml: 1 ml) and heated for 3 hours at the boil under reflux . The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was extracted with ethyl acetate and water, followed by separation and purification by column chromatography to obtain the title compound. 15 mg (11%).

¹ H-NMR (300 MHz, CD ₃ OD): δ 1.21 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.87 (sept., J = 6.9 Hz, 1H, CH) 3.85 (s, 3H, OCH ₃ ) 6.69 (s, 2H, ArH) 6.82 (d, J = 7.2 Hz, 1H, ArH) 6.90 (d, J = 7.8 Hz , 1H, ArH) 7.44-7.46 (m, 2H, ArH) 7.56 (br, 1H, ArH) 7.66 (br, 1H, ArH) 8.0 (m, 1H, ArH ) 8.67 (s, 1H, ArH).

<EXAMPLE 268> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl- 1H-indole-2-carboxamide

Fe powder (0.12 g, 2.20 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro 10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1-methyl-1H-indole-2-carboxamide (0.15 g, 0, 31 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 50 mg (35%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.82-2.86 (sept., 1H, CH) 3.89 ( s, 3H, CH ₃ ) 6.68 (s, 1H, ArH) 6.87-6.88 (m, 1H, ArH) 7.03-7.13 (m, 2H, ArH) 7.18 (s , 1H, ArH) 7.24-7.29 (m, 2H, ArH) 7.39-7.47 (m, 3H, ArH) 7.60 (d, J = 7.8 Hz, 1H, ArH) .

<EXAMPLE 269> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro- 6-fluorobenzo [b] thiophene-2-carboxamide

Powder Fe (0.05 g, 1.05 mmol), conc. HCl (0.02 ml) and water (0.5 ml) were added in this order to a solution of 3-chloro-6-fluoro-N- (4b- hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b] thiophene-2-carboxamide ( 80 mg, 0.14 mmol) in absolute ethanol (5 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to give the title compound. 50 mg (68%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.6 Hz, 6H, CH ₃ ) 2.76-2.85 (sept., 1H, CH) 6.69 ( s, 1H, ArH) 6.75 (d, J = 6.6 Hz, 1H, ArH) 6.84 (d, J = 7.5 Hz, 1H, ArH) 7.03 (d, J = 7, 2 Hz, 1H, ArH) 7.28 (t, J = 7.2 Hz, 1H, ArH) 7.43-7.48 (m, 2H, ArH) 7.66 (d, J = 8.7 Hz , 1H, ArH) 7.83-7.88 (m, 1H, ArH).

<EXAMPLE 270> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro- 6-methylbenzo [b] thiophene-2-carboxamide

Fe powder (0.11 g, 1.97 mmol), conc. HCl (0.05 ml) and water (1 ml) were added in this order to a solution of 3-chloro-N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH- benzo [d] indeno [1,2-b] furan-9b-yl) -6-methylbenzo [b] thiophene-2-carboxamide (0.15 g, 0.27 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to give the title compound. 21 mg (15%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.16-1.18 (m, 6H, CH ₃ ) 2.45 (s, 3H, CH ₃ ) 2.80-2.86 (sept., 1H, CH) 6.70 (s, 1H, ArH) 6.72-6.80 (m, 1H, ArH) 6.84-6.95 (m, 1H, ArH) 7.00-7.05 ( m, 1H, ArH) 7.33 (d, J = 8.1 Hz, 1H, ArH) 7.37-7.52 (m, 2H, ArH) 7.66 (s, 1H, ArH) 7.75 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 271> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,3- dimethyl-1H-pyrazolo [3,4-b] pyridine-5-carboxamide

Fe powder (137 mg, 2.45 mmol), conc. HCl (0.02 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -1,3-dimethyl-1H-pyrazolo [3,4-b] pyridin-5-carboxamide (180 mg, 0.35 mmol) in absolute ethanol (10 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by chromatography on a column (ethyl acetate: hexane = 1: 1) filled with silica gel treated with Et ₃ N to give the title compound (25 mg, 16%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.9 Hz, 6H), 2.54 (s, 3H), 2.80-2.89 (m, 1H) 4.03 (s, 3H), 6.68-6.71 (m, 2H), 6.88 (d, J = 7.6 Hz, 1H), 7.02 (d, J = 7.3 Hz, 1H), 7.42-7.50 (m, 2H), 8.71 (s, 1H), 8.94 (s, 1H).

<EXAMPLE 272> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2 -a] pyridine-6-carboxamide

Fe (80 mg, 1.42 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1, 2-a] pyridine-6-carboxamide (230 mg, 0.47 mmol) in a solvent ethanol: H ₂ O (10 ml: 1 ml) and heated for 4.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (5% methanol in methylene chloride) gave the title compound as a brown solid (50 mg, 23%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.03-1.42 (m, 6H), 3.05-3.30 (m, 1H), 6.61-6.75 (m, 2H ), 6.81-6.92 (m, 1H), 6.96-7.05 (m, 1H), 7.31-8.32 (m, 6H), 9.05-9.30 (m , 1H).

<EXAMPLE 273> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1,5 -a] pyrimidine-2-carboxamide

Fe (97 mg, 1.73 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1, 5-a] pyrimidine-2-carboxamide (280 mg, 0.58 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 3.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid (80 mg, 30%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.81 (sept., J = 6.8 Hz, 1H, CH) 6.63 ~ 6.72 (m, 2H, ArH), 6.83 ~ 6.87 (m, 1H, ArH), 7.00 ~ 7.12 (m, 3H, ArH), 7.43 ~ 7.51 (m, 2H, ArH), 8.55 ~ 8.57 (m, 1H, ArH), 8.96 (d, J = 7.3 Hz, 1H, ArH).

<EXAMPLE 274> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylbenzo [ b] thiophene-2-carboxamide

Fe powder (0.04 g, 0.85 mmol), conc. HCl (0.03 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -3-methylbenzo [b] thiophene-2-carboxamide (60 mg, 0.11 mmol) in absolute ethanol (5 ml) and heated for 2 hours under reflux a refrigerator. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min by column chromatography (ethyl acetate: hexane = 1: 4), filled with silica gel treated with Et ₃ N to give the title compound. 30 mg (53%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.00-1.27 (m, 6H), 2.53-2.64 (m, 3H), 2.70-2.84 (m, 1H ), 6.54-6.87 (m, 3H), 6.96-7.10 (m, 1H), 7.25-7.52 (m, 4H), 7.69-7.86 (m , 2H).

<EXAMPLE 275> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide

Fe powder (0.16 g, 2.92 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide (0.20 g, 0.40 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 68 mg (37%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.21 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.82-2.91 (sept., 1H, CH) 6.71 ( s, 1H, ArH) 6.91 (d, J = 7.5 Hz, 1H, ArH) 7.04 (d, J = 7.2 Hz, 1H, ArH) 7.47-7.49 (m, 2H, ArH) 7.90-7.98 (m, 3H, ArH) 8.15-8.28 (m, 2H, ArH) 9.40 (s, 1H, ArH).

<EXAMPLE 276> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyridazine-4-carboxamide

Fe powder (0.03 g, 0.55 mmol), conc. HCl (0.01 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) pyridazin-4-carboxamide (50 mg, 0.11 mmol) in absolute ethanol (5 ml) and was heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 26 mg (56%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.7 Hz, 6H, CH ₃ ) 2.78-2.87 (sept., 1H, CH) 6.68- 6.74 (m, 2H, ArH) 6.87 (d, J = 7.5 Hz, 1H, ArH) 7.02 (d, J = 7.2 Hz, 1H, ArH) 7.40-7, 48 (m, 2H, ArH) 8.04 (s, 2H, ArH) 9.32 (d, J = 5.0 Hz, 1H, ArH) 9.51 (s, 1H, ArH).

<EXAMPLE 277> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide

Fe powder (0.028 g, 0.50 mmol), conc. HCl (0.01 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide (50 mg, 0.11 mmol) in absolute ethanol (5 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (100% ethyl acetate), filled with Et ₃ N-treated silica gel to give the title compound. 38 mg (81%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.8 Hz, 6H, CH ₃ ) 2.83-2.89 (sept., 1H, CH) 6.75 ( s, 1H, ArH) 6.96 (d, J = 7.8 Hz, 1H, ArH) 7.47-7.54 (m, 3H, ArH) 8.08-8.24 (m, 3H, ArH ) 8.63 (s, 1H, ArH); 8.93 (s, 1H, ArH).

<EXAMPLE 278> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5 -a] pyridine-6-carboxamide

Fe (121 mg, 2.16 mmol) and 4 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1, 5-a] pyridine-6-carboxamide (350 mg, 0.72 mmol) in a solvent ethanol: H ₂ O (15 ml: 1.5 ml) and heated for 2.5 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid (269 mg, 80%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.85 (sept., J = 6.9 Hz, 1H, CH) 6.69-6.71 (m, 2H, ArH), 6.90 (d, J = 7.7 Hz, 1H, ArH), 7.02 (d, J = 7.2 Hz, 1H, ArH ), 7.43-7.46 (m, 2H, ArH), 8.07-8.18 (m, 2H, ArH), 9.65 (s, 1H, ArH).

<EXAMPLE 279> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5 -a] pyridine-8-carboxamide

Fe (55 mg, 0.99 mmol) and 3 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1, 5-a] pyridine-8-carboxamide (160 mg, 0.33 mmol) in ethanol: H ₂ O (15 ml: 1.5 ml) and heated for 2 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid (117 mg, 76%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.23 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.89 (sept., J = 6.9 Hz, CH), 6 70-6.74 (m, 2H, ArH), 6.95 (d, J = 7.8 Hz, 1H, ArH), 7.02 (d, J = 8.0 Hz, 1H, ArH), 7.44-7.55 (m, 3H, ArH), 8.41 (d, J = 7.3 Hz, 1H, ArH), 9.29 (d, J = 7.3 Hz, 1H, ArH) .

<EXAMPLE 280> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylimidazo [ 1,2-a] pyridin-2-carboxamide

Fe powder (0.27 g, 4.91 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide (0.49 g, 0.98 mmol) in absolute ethanol (10 ml). The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N to give the title compound. 80 mg (17%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 0.62-1.84 (m, 6H), 2.90-3.00 (m, 1H), 6.43-6.84 (m, 8H) 6.98-7.58 (m, 3H); 7.72-8.17 (m, 3H).

<EXAMPLE 281> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methyl [ 1,2,4] triazolo [1,5-a] pyrimidin-2-carboxamide

Fe powder (0.23 g, 4.22 mmol), conc. HCl (0.04 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -7-methyl [1,2,4] triazolo [1,5-a] pyrimidin-2-carboxamide (0.29 g, 0.57 mmol) in absolute ethanol (10 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (100% ethyl acetate), filled with Et ₃ N-treated silica gel to give the title compound. 0.17 g (62%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.82-2.85 (m, 4H, CH, CH ₃ ) 6, 67-6.74 (m, 2H, ArH) 6.87-6.94 (m, 1H, ArH) 7.00-7.04 (m, 1H, ArH) 7.30 (d, J = 4, 7 Hz, 1H, ArH) 7.44-7.51 (m, 2H, ArH) 8.81 (d, J = 4.6 Hz, 1H, ArH).

<EXAMPLE 282> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5,7- dimethylpyrazolo [1,5-a] pyrimidine-3-carboxamide

Fe powder (0.06 g, 1.16 mmol), conc. HCl (0.04 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -5,7-dimethylpyrazolo [1,5-a] pyrimidin-3-carboxamide (0.12 g, 0.23 mmol) in absolute ethanol (5 ml) and heated for 2 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (100% ethyl acetate), filled with Et ₃ N-treated silica gel to give the title compound. 60 mg (54%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.20 (dd, J = 6.9, 2.3 Hz, 6H, CH ₃ ) 2.53 (s, 3H, CH ₃ ) 2.76 ( s, 3H, CH ₃ ) 2.84-2.88 (m, 1H, CH) 6.71-6.80 (m, 2H, ArH) 6.90 (d, J = 7.8 Hz, 1H, ArH) 6.99 (s, 1H, ArH) 7.04 (d, J = 7.4 Hz, 1H, ArH) 7.42-7.51 (m, 2H, ArH) 8.39 (s, 1H , ArH).

<EXAMPLE 283> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide

Fe powder (76 mg, 1.37 mmol), conc. HCl (0.02 ml) and water (1.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide (220 mg, 0.46 mmol) in absolute ethanol (15 ml) and was heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 min using column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N, to obtain the title compound as a yellow solid (43 mg, 21%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.8 Hz, 6H), 2.84 (sept., J = 6.8 Hz, 1H), 6.50- 6.56 (m, 2H), 6.65-6.72 (m, 3H), 6.79 (s, 1H), 6.88 (d, J = 7.8 Hz, 1H), 7.01 (d, J = 7.4 Hz, 1H), 7.33 (d, J = 9.2 Hz, 1H), 7.44-7.48 (m, 1H), 7.87 (s, 1H) 8.02 (d, J = 7.0 Hz, 1H).

<EXAMPLE 284> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,6- diisopropyl-1H-pyrazolo [3,4-b] pyridin-4-carboxamide

Fe powder (78 mg, 1.39 mmol), conc. HCl (0.02 ml) and water (1.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -1,6-diisopropyl-1H-pyrazolo [3,4-b] pyridin-4-carboxamide (264 mg, 0.46 mmol) in absolute ethanol (15 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by chromatography on a column (ethyl acetate: hexane = 1: 1) filled with silica gel treated with Et ₃ N to afford the title compound as a white solid (79.5 mg, 32% )

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.6 Hz, 6H), 1.37 (d, J = 6.8 Hz, 6H), 1.54 (d , J = 4.4 Hz, 6H), 2.75-2.90 (m, 1H), 3.17-3.30 (m, 1H), 5.23-5.35 (m, 1H), 6.60-6.75 (m, 2H), 6.85-6.93 (m, 1H), 6.97-7.10 (m, 1H), 7.40-7.53 (m, 1H) ), 7.57 (s, 1H), 8.23 (s, 1H).

<EXAMPLE 285> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2 -a] pyrimidine-2-carboxamide

Fe powder (137 mg, 2.45 mmol), conc. HCl (0.02 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) imidazo [1,2-a] pyrimidin-2-carboxamide (110 mg, 0.23 mmol) in absolute ethanol (10 ml) and heated for 3 hours at the boil under reflux . The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by column chromatography (DCM: MeO = 10: 1), filled with silica gel treated with Et ₃ N to afford the title compound as a yellow solid (31 mg, 30%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.03-1.10 (m, 6H), 2.67-2.76 (m, 1H), 5.57-5.62 (m, 1H) , 6.40 (s, 1H), 6.63 (d, J = 8.7 Hz, 1H), 6.74 (d, J = 7.7 Hz, 1H), 6.91-6.67 ( m, 2H), 7.20 (d, J = 7.5 Hz, 1H), 7.46-7.52 (m, 1H), 7.56-7.64 (m, 1H), 7.95 (s, 1H), 8.34-8.39 (m, 1H), 8.63 (s, 1H).

<EXAMPLE 286> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-oxo- 1,2-dihydroisoquinoline-3-carboxamide

Fe powder (47 mg, 0.83 mmol), conc. HCl (0.02 ml) and water (0.9 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -1-oxo-1,2-dihydroisoquinoline-3-carboxamide (142 mg, 0.28 mmol) in absolute ethanol (9 ml) and heated for 3 hours at the boil with reflux condenser. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (EtOAc: hexane = 2: 1), filled with Et ₃ N-treated silica gel to give the title compound as a yellow solid (58 mg, 43%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H), 2.84 (sept., J = 6.9 Hz, 1H), 6.69 - 6.74 (m, 2H), 6.89 (d, J = 7.4 Hz, 1H), 7.02 (d, J = 7.5 Hz, 1H), 7.44-7.49 (m , 2H), 7.54 (s, 1H), 7.61-7.66 (m, 1H), 7.74-7.81 (m, 2H), 8.31 (d, J = 7.9 Hz, 1H).

<EXAMPLE 287> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3-methylimidazo [1,5-a] pyridin-1-carboxamide

Fe (77 mg, 1.38 mmol) and 4 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3-methylimidazo [1,5-a] pyridin-1-carboxamide (230 mg, 0.46 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 2 hours at the boil under reflux . After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1), N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d ] indeno [1,2-b] furan-9b-yl) -3-methylimidazo [1,5-a] pyridin-1-carboxamide as a yellow solid (90 mg, 42%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.63 (s, 3H, CH ₃ ), 2.85 (sept. , J = 6.8 Hz, 1H, CH), 6.67-6.74 (m, 2H, ArH), 6.81-6.89 (m, 2H, ArH), 7.00 ~ 7.09 (m, 2H, ArH), 7.42-7.49 (m, 2H, ArH), 7.93-7.96 (m, 1H, ArH), 8.09 (d, J = 7.4 Hz , 1H, ArH).

<EXAMPLE 288> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 2H-indazole-3-carboxamide

Fe (35 mg, 0.62 mmol) and 3 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2H-indazole-3-carboxamide (100 mg, 0.21 mmol) in a solvent ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 1) afforded the title compound N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH -benzo [d] indeno [1,2-b] furan-9b-yl) -2H-indazole-3-carboxamide as a yellow solid (63 mg, 66%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.15 (d, J = 6.9 Hz, 6H, CH ₃ ), 2.80 (sept., J = 6.9 Hz, 1H, CH) 6.66-6.72 (m, 2H, ArH), 6.86 (d, J = 7.9 Hz, 1H, ArH), 7.04 (d, J = 7.3 Hz, 1H, ArH ), 7.16-7.21 (m, 1H, ArH), 7.34-7.56 (m, 4H, ArH), 8.09 (d, J = 8.1 Hz, 1H, ArH).

<EXAMPLE 289> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [ 1,5-a] pyrimidine-6-carboxamide

Fe powder (62 mg, 1.12 mmol), conc. HCl (0.02 ml) and water (1.2 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [1,5-a] pyrimidine-6-carboxamide (186 mg, 0.37 mmol) in absolute ethanol (12 ml) and heated for 3 hours when boiling under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by column chromatography (EA: hexane = 1: 1), filled with Et ₃ N-treated silica gel to give the title compound as a yellow solid (125 mg, 72%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.17 (d, J = 6.9 Hz, 6H), 2.83 (sept., J = 7.1 Hz, 1H), 2.97 ( s, 3H), 6.68 (s, 1H), 6.70 (s, 1H), 6.71 (s, 1H), 6.87 (d, J = 7.7 Hz, 1H), 7, 06 (d, J = 7.2 Hz, 1H), 7.34-7.51 (m, 2H), 8.25-8.26 (m, 1H), 8.63 (s, 1H).

<EXAMPLE 290> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [ d] imidazole-2-carboxamide

Fe powder (54 mg, 0.96 mmol), conc. HCl (0.02 ml) and water (1.0 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide (155 mg, 0.32 mmol) in absolute ethanol (10 ml) and heated for 3 hours under reflux a refrigerator. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification by column chromatography (EA: hexane = 1: 1), filled with Et ₃ N-treated silica gel, to give the title compound as a yellow solid (67 mg, 46%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H), 2.84 (sept., J = 6.7 Hz, 1H), 6.68 ( s, 1H), 6.72 (s, 1H), 6.89 (d, J = 7.4 Hz, 1H), 7.03 (d, J = 7.3 Hz, 1H), 7.32 ( s, 1H), 7.34 (s, 1H), 7.44-7.50 (m, 2H), 7.55 (s, 1H), 7.69 (s, 1H).

<EXAMPLE 291> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro- 1H-benzo [d] imidazole-2-carboxamide

Fe powder (76 mg, 1.36 mmol), conc. HCl (0.02 ml) and water (1.5 ml) were added in this order to a solution of 5-fluoro-N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro- 4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide (227 mg, 0.45 mmol) in absolute ethanol (15 ml) and heated for 3 hours when boiling under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification by column chromatography (EA: hexane = 1: 1), filled with Et ₃ N-treated silica gel, to give the title compound as a yellow solid (144 mg, 68%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H), 2.85 (sept., J = 6.6 Hz, 1H), 6.67 ( s, 1H), 6.69 (d, J = 7.4 Hz, 1H), 6.90 (d, J = 7.3 Hz, 1H), 7.02 (d, J = 7.4 Hz, 1H), 7.12 (s, 1H), 7.25 (s, 1H), 7.45-7.51 (m, 2H), 7.73 (s, 1H).

<EXAMPLE 292> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5 -a] pyridine-5-carboxamide

Fe powder (0.17 g, 3.08 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) tetrazolo [1,5-a] pyridin-5-carboxamide (0.30 g, 0.61 mmol) in absolute ethanol (10 ml) and heated for 2 hours while boiling with reflux condenser. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 1), filled with silica gel treated with Et ₃ N to give the title compound. 0.11 g (40%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18-1.23 (m, 6H, CH ₃ ) 2.83-2.92 (sept., 1H, CH) 6.74 (m, 1H , ArH) 6.93 (d, J = 7.5 Hz, 1H, ArH) 7.05 (d, J = 6.9 Hz, 1H, ArH) 7.47-7.56 (m, 2H, ArH ) 7.89 (s, 1H, ArH) 7.99 (t, J = 7.2 Hz, 1H, ArH) 8.08 (d, J = 7.2 Hz, 1H, ArH) 8.36 (d , J = 7.8 Hz, 1H, ArH).

<EXAMPLE 293> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl- 1H-indazole-3-carboxamide

Fe powder (0.16 g, 2.92 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -1-methyl-3a, 7a-dihydro-1H-indazole-3-carboxamide (0.27 g, 0.54 mmol) in absolute ethanol (10 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 0.13 g (52%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80-2.88 (sept., 1H, CH) 4.12 ( s, 1H, CH ₃ ) 6.69-6.80 (m, 2H, ArH) 6.88 (d, J = 6.9 Hz, 1H, ArH) 7.04 (d, J = 6.6 Hz , 1H, ArH) 7.20-7.25 (m, 1H, ArH) 7.40-7.48 (m, 3H, ArH) 7.59 (d, J = 8.7 Hz, 1H, ArH) 8.07 (d, J = 8.4 Hz, 1H, ArH).

<EXAMPLE 294> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole- 5-carboxamide

Fe powder (0.04 g, 0.82 mmol), conc. HCl (0.03 ml) and water (0.5 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [ 1,2-b] benzofuran-9b-yl) -1H-indole-5-carboxamide (80 mg, 0.16 mmol) in absolute ethanol (5 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (ethyl acetate: hexane = 1: 2), filled with silica gel treated with Et ₃ N to give the title compound. 35 mg (47%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 7.2 Hz, 6H, CH ₃ ) 2.80-2.88 (sept., 1H, CH) 6.50- 6.53 (m, 1H, ArH) 6.69-6.72 (m, 2H, ArH) 6.80-6.85 (m, 1H, ArH) 7.03-7.12 (m, 2H, ArH) 7.29-7.31 (m, 1H, ArH) 7.37-7.47 (m, 2H, ArH) 7.60-7.63 (m, 1H, ArH) 8.16 (s, 1H, ArH).

<EXAMPLE 295> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl- 3a, 7a-dihydro-1H-indazole-3-carboxamide

Fe powder (0.08 g, 1.46 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -3-methyl- [1,2,4] triazolo [4,3-a] pyridin-8-carboxamide (0.13 g, 0.20 mmol) in absolute ethanol ( 10 ml) and heated for 23 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (100% ethyl acetate), filled with Et ₃ N-treated silica gel to give the title compound. 44 mg (46%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.21 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.77 (s, 3H, CH ₃ ) 2.84-3.30 ( sept., 1H, CH) 6.71-6.79 (m, 2H, ArH) 6.90 (d, J = 8.7 Hz, 1H, ArH) 7.03 (d, J = 5.7 Hz , 1H, ArH) 7.13 (t, J = 7.2 Hz, 1H, ArH) 7.46-7.48 (m, 2H, ArH) 8.04 (d, J = 6.3 Hz, 1H , ArH) 8.48 (d, J = 7.2 Hz, 1H, ArH).

<EXAMPLE 296> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl- 1H-imidazole-4-carboxamide

Fe powder (0.09 g, 1.62 mmol), conc. HCl (0.03 ml) and water (1 ml) were added in this order to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) -1-methyl-1H-imidazole-4-carboxamide (0.10 g, 0.22 mmol) in absolute ethanol (10 ml) and heated for 3 hours under reflux a refrigerator. The reaction mixture was washed with ethyl acetate and filtered to remove Fe powder. The filtrate was made basic with NaHCO ₃ and washed many times with water. The organic layer was dried and filtered, followed by purification for 30 minutes by column chromatography (100% ethyl acetate), filled with Et ₃ N-treated silica gel to give the title compound. 29 mg (31%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.80-2.86 (sept., 1H, CH) 6.66- 6.69 (m, 2H, ArH) 6.87 (d, J = 7.2 Hz, 1H, ArH) 6.99 (d, J = 7.2 Hz, 1H, ArH) 7.41-7, 45 (m, 2H, ArH) 7.57-7.61 (m, 2H, ArH).

<EXAMPLE 297> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole- 3-carboxamide

Fe powder (31 mg, 0.55 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole -3-carboxamide (0.08 g, 0.18 mmol) in a solvent ethanol: water (10: 1, 10 ml) and heated for 3 hours at the boil under reflux. The reaction mixture was washed with ethyl acetate and filtered while hot to remove Fe powder. The filtrate was concentrated in vacuo and purified by silica gel column chromatography (30% ethyl acetate mixed with 60% hexane) to give the title compound. 35 mg (47%).

¹ H-NMR (300 MHz, CD ₃ OD): δ 1.18 (d, J = 6.9 Hz, 6H, CH ₃ ) 2.84 (sept., 1H, CH) 6.53-6.58 (m, 1H, ArH) 6.64-6.76 (m, 3H, ArH) 6.86-6.90 (m, 1H, ArH) 6.98-7.01 (m, 1H, ArH) 7 36-7.46 (m, 3H, ArH).

<EXAMPLE 298> tert-Butyl (tert-butoxycarbonylamino) (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino ) methylene carbamate

4b, 9b-Dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (0.30 g, 1.02 mmol) was dissolved in 5 ml of THF and stirred together with DEAD (0.24 ml, 1.56 mmol) and PPh ₃ (0.41 g, 1.56 mmol) for 5 min, and then with Boc-guanidine (0.40 g, 1.56 mmol) ) for 3 hours at room temperature. Thereafter, vacuum concentration was carried out, followed by purification using column chromatography (ethyl acetate: hexane = 1: 2) to obtain the title compound. 40 mg (7%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.15 (d, J = 6.8 Hz, 6H), 1.30 (s, 9H), 1.50 (s, 9H), 2.81 ( q, J = 7.3 Hz, 1H), 6.69 (s, 1H), 6.81 (d, J = 7.5 Hz, 1H), 7.30 (d, J = 7.9 Hz , 1H), 7.51 (t, J = 8.7 Hz, 1H), 7.67 (s, 1H), 7.73-7.82 (m, 2H), 8.00 (d, J = 7.9 Hz, 1H), 9.36 (s, 1H), 11.17 (s, 1H).

<EXAMPLE 299> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indazole- 5-carboxamide

Fe powder (104 mg, 1.86 mmol) and 4 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-indazole-5-carboxamide (300 mg, 0.62 mmol) in a solvent ethanol: H ₂ O (20 ml: 2 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 2: 1) gave the title compound as a yellow solid. 90 mg (32%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.19 (d, J = 6.8 Hz, 6H, CH ₃ ), 2.85 (m, 1H, CH), 6.67-6.74 (m, 2H, ArH), 6.89 (d, J = 8.0 Hz, 1H, ArH), 7.02 (d, J = 7.4 Hz, 1H, ArH), 7.43-7, 56 (m, 3H, ArH), 7.85-7.88 (m, 1H, ArH), 8.13 (s, 1H, ArH), 8.38 (s, 1H, ArH).

<EXAMPLE 300> N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methyl- 1H-pyrazole-5-carboxamide

Fe powder (36 mg, 0.65 mmol) and 2 drops conc. HCl was successively added to a solution of N- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3-methyl-1H-pyrazole-5-carboxamide (90 mg, 0.22 mmol) in a solvent ethanol: H ₂ O (10 ml: 1 ml) and heated for 3 hours at the boil under reflux. After vacuum concentration, purification by column chromatography (EtOAc: hexane = 1: 2) gave the title compound as a yellow solid. 62 mg (74%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 1.18 (d, J = 6.9 Hz, 1H, CH ₃ ), 2.29 (s, 3H, CH ₃ ), 2.84 (sept. , J = 6.9 Hz, 1H, CH), 6.42 (s, 1H, ArH), 6.66-6.70 (m, 2H, ArH), 6.87 (d, J = 8.0 Hz, 1H, ArH), 6.99 (d, J = 7.4 Hz, 1H, ArH), 7.41-7.47 (m, 2H, ArH).

<EXAMPLE 301> 1-amino-9b- (furan-2-carboxamido) -7-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylfuran-2- carboxylate

HATU (0.35 g, 3.52 mmol) was added at 0 ° C to a solution of furan-2-carboxylic acid (0.20 g, 1.85 mmol) in anhydrous dimethylformamide (3 ml) and the mixture was then stirred with Et ₃ N (0.70 g, 1.85 mmol) and 9b-amino-4b-hydroxy-7-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (0.50 g, 1.76 mmol) at room temperature for 24 hours. The reaction mixture was diluted in ethyl acetate and washed repeatedly with an aqueous solution of K ₂ CO ₃ and brine, the organic layer was dried and filtered. Purification by column chromatography (ethyl acetate: hexane = 1: 1) gave the title compound. 13 mg (1.5%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 3.76 (m, 3H, OMe), 6.39-6.50 (m, 2H, ArH), 6.65 (m, 1H, ArH), 6 93-6.95 (m, 2H, ArH); 7.12 (d, J = 3.9 Hz, 1H, ArH). 7.38 (s, 1H, ArH), 7.47 (s, 1H, ArH), 7.51-7.54 (m, 1H, ArH), 7.63 (t, J = 7.5 Hz, 1H, ArH), 7.84 (t, J = 7.2 Hz, 1H, ArH), 7.93 (d, J = 7.5 Hz, 1H, ArH), 8.09 (t, J = 7 8 Hz, 1H, ArH).

<EXAMPLE 302> N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide

A solution of nicotinic acid (409 mg, 2.14 mmol) in DCM was cooled to 0 ° C. The mixture was stirred with EDCI (332 mg, 2.14 mmol) for 10 minutes, then with DMF (3 ml) for an additional 10 minutes, and finally with HOBt (289 mg, 2.14 mmol) and 9b amino-4b-hydroxy-7,8-dimethyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (500 mg, 1.78 mmol) for 15 hours at room temperature. Subsequently, the reaction mixture was mixed with DCM, washed with water and dried with Na ₂ SO ₄ . After filtration and concentration, purification by column chromatography afforded the title compound as a solid. 178 mg (26%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 2.19 (s, 3H), 2.22 (s, 3H), 6.60 (s, 1H), 7.29 (s, 1H), 7 , 49-7.52 (m, 1H), 7.66-7.88 (m, 4H), 8.25 (d, J = 2.1 Hz, 1H), 8.66 (d, J = 3 4 Hz, 1H); 8.99 (s, 1H).

<EXAMPLE 303> N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2- carboxamide

9b-amino-4b-hydroxy-7,8-dimethyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one (500 mg, 1.78 mmol) and 1H-pyrrole-2-carboxylic acid (238 mg, 2.14 mmol) was dissolved in DCM (17.8 ml, 0.1 M), mixed with DCC (442 mg, 2.14 mmol) at room temperature with stirring. The reaction mixture was washed with water, dehydrated with Na ₂ SO ₄ , filtered and concentrated, followed by purification by column chromatography to obtain the title compound as a solid. 40 mg (6%).

¹ H-NMR (300 MHz, CD ₃ OD) δ 2.17 (s, 3H), 2.19 (s, 3H), 6.3-6.15 (m, 1H), 6.58 (s, 1H), 6.88 (s, 1H), 6.92 (d, J = 3.7 Hz, 1H), 7.28 (s, 1H), 7.54-7.59 (m, 1H), 7.75-7.82 (m, 1H); 7.91-7.93 (m, 1H).

<EXAMPLE 304> N- (6-Ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide

Pyrrole-2-carboxylic acid (133 mg, 1.96 mmol) and 9b-amino-6-ethyl-4b-hydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 g, 1.78 mmol) were dissolved together in methylene chloride (10 ml) and mixed with DCC (367 mg, 1.78 mmol) at room temperature for 20 hours with stirring. After extraction with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (EA: Hex = 1: 1) afforded the title compound as a yellow solid. 151 mg (23%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (t, J = 7.5 Hz, 3H, CH ₃ ), 2.64 (q, J = 7.5 Hz, 2H, CH ₂ ) 5.93 (s, 1H, OH), 6.26 (s, 1H, ArH), 6.79 (s, 1H, ArH), 6.85-6.98 (m, 3H, ArH), 7 21-7.26 (m, 1H, ArH), 7.56 (t, J = 7.6 Hz, 1H, ArH), 7.80-7.85 (m, 2H, ArH), 8.04 (d, J = 7.8 Hz, 1H, ArH).

<EXAMPLE 305> N- (6-Ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide

Furan-2-carboxylic acid (239 mg, 2.13 mmol) was dissolved in methylene chloride (10 ml) and mixed with EDCI (406 mg, 2.13 mmol) and HOBt (288 mg, 2.13 mmol) for 10 min. followed by 9b-amino-6-ethyl-4b-hydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 mg, 1.78 mmol) overnight at room temperature with stirring. After extraction with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (EA: Hex = 1: 2) afforded the title compound as a yellow solid. 180 mg (27%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.17 (t, J = 7.5 Hz, 3H, CH ₃ ), 2.63 (q, J = 7.5 Hz, 2H, CH ₂ ) 5.63 (br, 1H, OH), 6.51 (q, 1.7 Hz, 1H, ArH), 6.89 (t, J = 7.6 Hz, 1H, ArH), 7, 09-7.14 (m, 2H, ArH), 7.23-7.26 (m, 1H, ArH), 7.46 (s, 1H, NH), 7.52 (s, 1H, ArH), 7.56 (t, J = 7.5 Hz, 1H, ArH), 7.79-7.85 (m, 2H, ArH), 8.04 (d, J = 7.8 Hz, 1H, ArH) .

<EXAMPLE 306> N- (8-Chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide

Quinoline-4-carboxylic acid (361 mg, 1.74 mmol) was dissolved in methylene chloride (10 ml) and mixed with EDCI (397 mg, 2.08 mmol) and HOBt (281 mg, 2.08 mmol) for 10 min. followed by 9b-amino-6-ethyl-4b-hydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 mg, 1.74 mmol) overnight at room temperature with stirring. After extraction with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (EA: Hex = 1: 1) afforded the title compound as a white solid. 112 mg (15%).

¹ H-NMR (500 MHz, CDCl ₃ ) δ 6.86 (d, J = 8.6 Hz, 1H, ArH), 7.19 (s, 1H, NH), 7.27 ~ 7.29 (m , 1H, ArH), 7.43 (d, J = 2.1 Hz, 1H, ArH), 7.53 (d, J = 4.2 Hz, 1H, ArH), 7.60-7.65 ( m, 2H, ArH), 7.78 (t, J = 7.9 Hz, 1H, ArH), 7.87-7.91 (m, 2H, ArH), 8.06-8.11 (m, 2H, ArH), 8.16 (d, J = 8.1 Hz, 1H, ArH), 8.98 (d, J = 4.2 Hz, 1H, ArH).

<EXAMPLE 307> N- (8-Chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrahydrofuran-2-carboxamide

Tetrahydrofuran-2-carboxylic acid (242 mg, 2.08 mmol) was dissolved in methylene chloride (10 ml) and mixed with EDCI (397 mg, 2.08 mmol) and HOBt (281 mg, 2.08 mmol) for 10 min. followed by 9b-amino-6-ethyl-4b-hydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one (500 mg, 1.74 mmol) overnight at room temperature with stirring. After extraction with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated in vacuo. Purification by column chromatography (EA: Hex = 1: 1) afforded the title compound as a yellow solid. 183 mg (27%).

¹ H-NMR (300 MHz, CDCl ₃ ) δ 1.88-1.95 (m, 3H, CH ₂ ), 2.17-2.30 (m, 1H, CH ₂ ), 3.88-3, 95 (m, 1H, OCH ₂ ), 3.98-4.09 (m, 1H, OCH ₂ ), 4.29-4.40 (m, 1H, OCH), 6.75-6.77 (m , 1H, ArH), 7.19-7.21 (m, 1H, ArH), 7.30-7.34 (m, 1H, ArH), 7.57 (t, J = 7.3 Hz, 1H , ArH), 7.79-7.84 (m, 2H, ArH), 7.97-7.99 (m, 1H, ArH).

Table 1 shows the chemical formulas of the compounds of examples 1-307.

TABLE 1 Etc. Chemical structure Etc. Chemical structure one

150

2

151

3

152

four

153

5

154

6

155

7

156

8

157

9

158

10

159

eleven

160

12

161

13

162

fourteen

163

fifteen

164

16

165

17

166

eighteen

167

19

168

twenty

169

21

170

22

171

23

172

24

173

25

174

26

175

27

176

28

177

29th

178

thirty

179

31

180

32

181

33

182

34

183

35

184

36

185

37

186

38

187

39

188

40

189

41

190

42

191

43

192

44

193

45

194

46

195

47

196

48

197

49

198

fifty

199

51

200

52

201

53

202

54

203

55

204

56

205

57

206

58

207

59

208

60

209

61

210

62

211

63

212

64

213

65

214

66

215

67

216

68

217

69

218

70

219

71

220

72

221

73

222

74

223

75

224

76

225

77

226

78

227

79

228

80

229

81

230

82

231

83

232

84

233

85

234

86

235

87

236

88

237

89

238

90

239

91

240

92

241

93

242

94

243

95

244

96

245

97

246

98

247

99

248

one hundred

249

101

250

102

251

103

252

104

253

105

254

106

255

107

256

108

257

109

258

110

259

111

260

112

261

113

262

114

263

115

264

116

265

117

266

118

267

119

268

120

269

121

270

122

271

123

272

124

273

125

274

126

275

127

276

128

277

129

278

130

279

131

280

132

281

133

282

134

283

135

284

136

285

137

286

138

287

139

288

140

289

141

290

142

291

143

292

144

293

145

294

146

295

147

296

148

297

149

298

- - 299

- - 300

- - 301

- - 302

- - 303

- - 304

- - 305

- - 306

- - 307

<EXPERIMENTAL EXAMPLE 1> Analysis of inhibition of cytopathic action (CPE) for antiviral activity against picornaviruses

HeLa cells (human cervical cancer cells), MRC-5 (human embryonic fibroblasts) and RD (cells derived from human rhabdomyosarcoma) were used in the analysis. For comparison, ribavirin (Riv), pleconaryl (pleco) and BTA-798 (BTA) were used as controls. The reagents were dissolved to a concentration of 10-40 mg / ml in 100% dimethyl sulfoxide (DMSO). Water-soluble reagents were dissolved in PBS (-) and stored at -20 ° C. On the day of the experiment, they were used at a concentration of 3x-5x so that the concentration of dimethyl sulfoxide in each well ranged from 0.5% to 1%.

Pharmaceutical effects were determined using a virus-induced cytopathic effect (CPE) inhibition assay. For this, cells suitable for viruses were grown in 96-well plates, diluted in DME with 2% FBS (DME / 2% FBS) or MEM with 2% FBS (MEM / 2% FBS) viruses were inoculated into each well of the tablet in an amount of 100 μl with a concentration corresponding to 100 CCID ₅₀ (50% infectious dose for cell culture) and incubated for 30 min - 1 hour at 33 ° C or 37 ° C, ensuring the penetration of viruses into the cells. The culture medium was removed before adding to each well an aliquot of the drug, diluted in various concentrations, in an amount of 100 μl. While HRV was grown at 33 ° C, other viruses were incubated at 37 ° C in a CO ₂ incubator for 2-3 days. Alternatively, the cells were cultured for 2-3 days without removing the medium, and then 50 μl of each drug was added to them with a 2-fold increase in dilution, and then 50 μl of the diluted virus.

The test conditions for each virus are summarized in table 2 below.

TABLE 2 Virus Note Host cell Incubation Temp. Incubation Term Wednesday Koksaki A9 - RD 37 ° C 2 days MEM / 2% FBS Koksaki A24 - MRC-5 37 ° C 2 days MEM / 2% FBS Koksaki A24 Highlighted in Patients MRC-5 37 ° C 2 days MEM / 2% FBS Koksaki B1 - Hela 37 ° C 2 days DME / 2% FBS Koksaki B3 - Hela 37 ° C 2 days DME / 2% FBS Koksaki B4 - Hela 37 ° C 2 days DME / 2%

Fbs Entero 70 - MRC-5 37 ° C 2 days MEM / 2% FBS Poliovirus3 - Hela 37 ° C 2 days DME / 2% FBS Rhinovirus - Hela 33 ° C 3 days MEM / 2% FBS

For HeLa cells, drugs were measured at an EC ₅₀ (50% of the maximum effective concentration), which is the concentration of the drug causing a response equal to the middle between the baseline and maximum using MTT analysis. For RD and MRC-5 cells, CPE was determined using FDA (fluorescein diacetate). To evaluate the results of the strength of the activity of the drug to reflect the toxic effect of the drug, mock-infected cells, which were obtained by adding virus-free medium to the cell culture, were treated in a similar manner. That is, the medium was removed, then incubated for one hour and diluted drugs were added to the medium again. After an incubation of 2–3 days, cells were observed under a microscope and CC ₅₀ drugs (50% cytotoxic concentration) were determined using an MTT assay, in which viable cells in mock-infected drug containing wells were counted, compared with the number of viable cells in control wells containing no drugs. In the FDA hydrolysis assay, FDA was added to each well, then the medium was removed and incubated for 20-30 minutes, and then the fluorescence intensity was measured using a CPE spectrofluorimeter, similar to the method in MTT.

The survival rate (% survival) of mock-infected cells was calculated using the following mathematical formula 1:

[Mathematical Formula 1]

While 100% cell survival means the absence of drug cytotoxicity, the maximum cytotoxicity corresponds to 0% cell survival. A 50% cytotoxic concentration (CC ₅₀ ) was determined as the concentration required to reduce the number of cells by 50% compared with untreated controls. Highest CC ₅₀ values indicate less cytotoxicity.

In addition, antiviral effects can be calculated using the following mathematical formula 2:

[Mathematical formula 2]

A survival rate of 100% means an excellent antiviral effect (100%), while drugs are considered to be devoid of antiviral activity with a survival rate of 0%. Viral cytopathic effect (CPE) was recorded and a 50% effective concentration (EC ₅₀ ) was determined as the concentration of the compound required to reduce the viral CPE by 50% compared to the untreated control. Lower EC ₅₀ values mean higher antiviral activity.

The CC ₅₀ and EC ₅₀ values of compounds for which cytotoxicity and antiviral activity against picornaviruses were considered are shown in Tables 3 and 4, respectively.

6 47.51 - - - - - - - 7 > 50 - - - - - - - 8 44.1 - - - - - - - 9 eighteen <0.01 0,027 - - - - - 10 14.2 <0.01 <0.01 - 18.43 - - <1.0 eleven 16,2 <0.01 <0.01 - - - - - 12 > 50 - - - - - - - 13 8.08 - - - - - - - fourteen > 50 - - - - - - - fifteen 8.57 - - - - - - - 16 7.82 - - - - - - - 17 7.85 - - - - - - - eighteen 37.48 - - - - - - - 19 8.34 - - - - - - - twenty 7.93 - - - - - - - 21 32.1 - - - - - - - 22 8.01 - - - - - - - 23 9.3 - - - - - - - 24 8.8 0.013 - - - - - - 25 > 50 - - - - - - -

26 <4 - - - - - - - 27 43.9 - - - - - - - 28 9.2 - - - - - - - 29th 7.49 0.355 - - - - - - thirty 45.5 0.014 - - - - - - 31 8.9 - - - - - - - 32 8.1 - - - - - - - 33 > 50 - - - - - - - 34 > 50 - - - - - - - 35 46.69 <0.01 - - - - - - 36 9.34 <0.01 - - - - - - 37 9.68 <0.01 - - - - - - 38 9.5 <0.01 - - - - - - 39 45.12 - - - - - - - 40 43.96 <0.01 - - - - - - 41 27.14 <0.01 - - - - - - 42 8.94 - - - - - - - 43 33.17 <0.01 - - - - - - 44 6.25 - - - - - - - 45 12.23 <0.01 - - - - - -

46 9.42 <0.01 - <0.01 18.33 <0.01 - - 47 15.38 <0.01 <0.01 <0.1 - - - - 48 35.01 - - - - - - - 49 9.18 0.373 - - - - - - fifty 49.89 <0.01 <0.01 <0.1 - - - - 51 17.47 <0.01 <0.01 - - - - - 52 > 50 - - - - - - - 53 45.65 0.04 - - - - - - 54 > 50 0.014 0.0147 - - - - - 55 7.49 0,084 - - - - - - 56 42.16 0,0784 - - - - - - 57 46.66 0.35 - - - - - - 58 > 50 - - - - - - - 59 > 50 - - - - - - - 60 10.56 <0.01 <0.01 - - - - - 61 > 50 <0.01 <0.01 - - - - - 62 > 50 <0.01 <0.01 - - - - - 63 > 50 <0.01 - - - - - - 64 8.13 <0.01 <0.01 - - - - - 65 18.19 <0.01 0.015 - - - - -

66 44.72 <0.01 <0.01 - - - - - 67 9.42 0.596 - - - - - - 68 8.94 <0.01 <0.01 - - - - - 69 70 0.43 - - - - - - 70 47.08 <0.01 <0.01 - - - - - 71 38.85 <0.01 <0.01 <0.1 - - - - 72 43.91 <0.01 <0.01 - - - - - 73 47.08 <0.01 <0.01 <0.01 56.4 <0.01 <1.0 <1.0 74 9.26 <0.01 <0.01 - - - - - 75 46.66 <0.01 <0.01 - - - - - 76 > 50 - - - - - - - 77 > 50 <0.01 <0.01 - 53.86 <0.01 - - 78 47.74 0,025 - - 20.65 <0.01 - - 79 10.43 - - - - - - - 80 47.51 0.0139 - - - - - - 81 8.61 - - - - - - - 82 1.9 - - - - - - - 83 46.25 - - - - - - - 84 > 50 - - - - - - - 85 19.25 - - - - - - -

86 - - - - - - - - 87 36.77 <0.01 <0.01 - - - - - 88 8.16 0.017 - - - - - - 89 > 50 <0.01 <0.01 - - - - - 90 33.95 <0.01 <0.01 - - - - - 91 > 50 - - - - - - - 92 > 50 - - - - - - - 93 8.49 <0.01 <0.01 - 6.23 <0.01 - - 94 42.39 <0.01 <0.01 - 58.06 <0.01 - - 95 38.07 <0.01 <0.01 - 25,99 <0.01 - - 96 > 50 <0.01 <0.01 0.016 23.97 <0.01 - - 97 > 50 <0.01 <0.01 - 8.8 <0.01 - - 98 7.8 <0.01 0,022 - - - - - 99 > 50 <0.01 <0.01 - 7.7 0.0101 - - one hundred 40.64 - - - - - - - 101 > 50 - - - - - - - 102 > 50 - - - - - - - 103 > 50 - - - - - - - 104 > 50 0.015 - - - - - -

105 > 50 0.018 0.016 - - - - - 106 3.53 - - - - - - - 107 > 50 - - - - - - - 108 1.81 - - - - - - - 109 > 50 - - - - - - - 110 14.41 - - - - - - - 111 43.58 <0.01 <0.01 - - - - - 112 41.98 <0.01 <0.01 - - - - - 113 45.46 <0.01 <0.01 <0.01 48.78 <0.01 <1.0 - 114 45.85 <0.01 <0.01 0,034 43.12 <0.01 - - 115 42.79 <0.01 <0.01 <0.01 23.11 <0.01 - - 116 41.72 <0.01 <0.01 - - - - - 117 > 50 0.012 - - - - - - 118 > 50 <0.01 <0.01 - - - - - 119 38.22 0,027 - - - - - - 120 8.16 - - - - - - - 121 > 50 0.02 - - - - - - 122 11.96 - - - - - - - 123 37.54 <0.01 <0.01 <0.01 43.35 <0.01 <1.0 - 124 > 50 - - - - - - -

125 45.46 - - - - - - - 126 47.06 - - - - - - - 127 37.61 - - - - - - - 128 37.31 - - - - - - - 129 6.79 - - - - - - - 130 > 50 - - - - - - - 131 2.05 <0.01 <0.01 - - - - - 132 0.72 0,03 - - - - - - 133 1,58 <0.01 - - - - - - 134 6.69 - - - - - - - 135 10.94 - - - - - - - 136 7.8 - - - - - - - 137 39.97 <0.01 <0.01 - - - - - 138 38.8 - - - - - - - 139 0.45 - - - - - - - 140 2.08 - - - - - - - 141 3.47 - - - - - - - 142 18.68 - - - - - - - 143 > 50 <0.01 <0.01 <0.01 58.06 <0.01 <1.0 - 144 35.48 <0.01 <0.01 <0.01 21.71 <0.01 <1.0 - 145 18.33 0,026 - - - - - -

146 1,53 - - - - - - - 147 32.88 - - - - - - - 148 1.72 - - - - - - - 149 8.48 - - - - - - - 150 1.32 - - - - - - - 151 1,52 0.04 - - - - - - 152 0.9 - - - 10.52 - - - 153 9.02 <0.01 <0.01 <0.01 16.03 <0.01 <1.0 <1.0 154 46.23 <0.01 <0.01 <0.01 22.71 <0.01 <1.0 <1.0 155 9.02 <0.01 <0.01 <0.01 7.81 <0.01 <1.0 <1.0 156 36.38 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 157 > 100 <0.01 <0.01 - 28.49 - - - 158 44.72 <0.01 <0.01 <0.01 39.42 <0.01 <1.0 - 159 44.72 0,021 - - 42.39 - - - 160 47.19 <0.01 <0.01 - 18.52 - - - 161 40.73 <0.01 <0.01 <0.01 17.89 <0.01 <1.0 - 162 > 10 - - - > 10 - - - 163 > 10 - - - > 10 - - - 164 > 10 0.04 0.04 - > 10 - - - 165 > 10 <0.01 <0.01 - > 10 <0.01 - -

166 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 167 > 10 <0.01 0,034 - > 10 0,038 - - 168 > 10 0.04 - - > 10 - - - 169 > 10 - - - > 10 - - - 170 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 171 > 10 <0.01 <0.01 0,03 > 10 - <1.0 <1.0 172 > 10 <0.01 0,027 - > 10 0.0125 - - 173 > 10 0,036 - - > 10 - - - 174 > 10 <0.01 <0.01 0.019 > 10 <0.01 - - 175 > 11 <0.01 <0.01 <0.01 > 10 <0.01 - - 176 > 10 0,037 0,037 - > 10 - - - 177 > 10 <0.01 <0.01 - > 10 <0.01 - - 178 > 10 <0.01 0,035 - > 10 - - - 179 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 180 4.32 <0.01 <0.01 0,033 > 10 0.0114 - - 181 > 10 <0.01 <0.01 0,036 > 10 0.0124 - - 182 6.42 <0.01 0,022 - 5.85 0,035 - - 183 8.54 <0.01 <0.01 0.014 > 10 <0.01 - - 184 36.38 <0.01 0,025 - > 10 - - -

185 7.18 0,028 - - > 10 - - - 186 8.31 <0.01 <0.01 0,026 > 10 <0.01 - - 187 7.43 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 188 8.38 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 189 8.56 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 190 > 10 <0.01 <0.01 <0.01 5.52 <0.01 <1.0 <1.0 191 4.12 <0.01 <0.01 <0.01 > 10 <0.01 - <1.0 192 > 10 <0.01 <0.01 - > 10 - - - 193 > 10 <0.01 <0.01 0.011 > 10 <0.01 <1.0 - 194 > 10 <0.01 <0.01 - > 10 <0.01 - - 195 - - - - - - - - 196 48.47 <0.01 <0.01 - 16.18 - - - 197 34.45 <0.01 <0.01 <0.01 16.03 <0.01 - - 198 > 50 <0.01 <0.01 <0.01 27.94 <0.01 <1.0 <1.0 199 48.28 <0.01 <0.01 <0.01 42.95 <0.01 <1.0 <1.0 200 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 201 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 202 9.6 <0.01 <0.01 - 3.24 <0.01 - - 203 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0

204 > 4.51 <0.01 <0.01 0.011 > 10 <0.01 - <1.0 205 > 10 <0.01 <0.01 0,036 > 10 <0.01 - - 206 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 207 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 208 > 10 <0.01 <0.01 - > 10 <0.01 - - 209 > 10 <0.01 <0.01 0,036 8.43 <0.01 - - 210 > 10 <0.01 <0.01 - > 10 - - - 211 > 10 <0.01 <0.01 - > 10 0,039 - - 212 > 10 <0.01 <0.01 <0.01 > 10 <0.01 - <1.0 213 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 214 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 215 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 216 4.75 0,036 0,037 - 9.69 - - - 217 4.24 <0.01 <0.01 0,038 > 10 <0.01 - - 218 8.49 <0.01 <0.01 - > 10 <0.01 - - 219 45.12 <0.01 <0.01 - > 10 <0.01 - - 220 > 50 - - - > 10 - - - 221 14.5 <0.01 <0.01 0.016 6.53 <0.01 - - 222 39.43 <0.01 <0.01 - > 10 0,037 - -

223 7.46 <0.01 <0.01 <0.01 4.36 - - - 224 > 50 <0.01 0.013 - > 10 - - - 225 22.87 <0.01 <0.01 - > 10 - - - 226 28.18 <0.01 <0.01 - > 10 - - - 227 9.62 <0.01 <0.01 - > 10 - - - 228 24.08 <0.01 <0.01 - > 10 0,029 - - 229 8.63 <0.01 <0.01 - 4,51 0,036 - - 230 42.83 <0.01 <0.01 - > 10 <0.01 <1.0 - 231 8.64 <0.01 <0.01 <0.01 > 10 <0.01 - - 232 > 50 0.012 0.024 - > 10 - - - 233 31.89 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 234 9.1 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 235 7.97 <0.01 <0.01 <0.01 8.88 <0.01 <1.0 <1.0 236 21.36 - - - > 10 - - - 237 6.27 - - - > 10 - - - 238 8.33 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 239 > 50 <0.01 <0.01 - > 10 - - - 240 8.25 <0.01 <0.01 <0.01 > 10 <0.01 - - 241 7.86 <0.01 <0.01 - > 10 - - -

242 8.55 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 243 7.36 <0.01 <0.01 <0.01 > 10 <0.01 - - 244 15.71 <0.01 <0.01 <0.01 > 10 <0.01 - <1.0 245 8.47 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 246 9.84 <0.01 <0.01 <0.01 > 10 <0.01 - - 247 twenty <0.01 0.013 - > 10 0,036 - - 248 4.99 <0.01 <0.01 0,027 > 10 <0.01 - - 249 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 250 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 251 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 252 3.64 <0.01 <0.01 <0.01 3.53 <0.01 - - 253 > 10 <0.01 <0.01 <0.01 > 10 <0.01 - - 254 > 10 <0.01 <0.01 - > 10 <0.01 - - 255 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 256 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 257 > 10 <0.01 <0.01 0,031 > 10 <0.01 - - 258 > 10 <0.01 <0.01 0.04 > 10 <0.01 <1.0 - 259 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 260 > 10 <0.01 <0.01 0.04 > 10 <0.01 - -

261 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 262 > 10 <0.01 <0.01 0.0124 > 10 <0.01 - - 263 7.65 <0.01 <0.01 0,039 5,4 <0.01 - - 264 > 10 0.011 0,035 - > 10 0,034 - - 265 4.75 <0.01 <0.01 <0.01 4.4 <0.01 <1.0 <1.0 266 6.41 <0.01 <0.01 <0.01 > 10 <0.01 - - 267 0.87 <0.01 <0.01 - 0.86 0.012 <1.0 <1.1 268 9.28 <0.01 <0.01 0,036 > 10 <0.01 - <1.0 269 > 10 0.018 0,035 - > 10 0,036 - - 270 6.57 0,03 0,036 - 5.93 0,039 - - 271 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 272 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 273 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 274 > 10 <0.01 0,027 0,036 > 10 <0.01 - <1.0 275 4.78 <0.01 <0.01 0,035 4,55 <0.01 - - 276 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 277 > 10 <0.01 <0.01 - > 10 0,026 - - 278 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 <1.0 279 7.88 <0.01 <0.01 0,035 4.94 <0.01 <1.0 <1.0

280 > 10 <0.01 <0.01 - > 10 <0.01 - - 281 > 10 <0.01 <0.01 0,025 > 10 <0.01 - - 282 6.78 <0.01 0.011 - > 10 0.011 - - 283 5.47 0.024 - - > 10 0.024 - - 284 4,56 <0.01 0.016 - 3.71 0,028 - - 285 > 10 <0.01 <0.01 <0.01 > 10 <0.01 <1.0 - 286 4.28 <0.01 <0.01 <0.01 4.04 <0.01 <1.0 <1.0 287 7.01 <0.01 <0.01 0,036 > 10 <0.01 - - 288 > 10 <0.01 <0.01 0,029 > 10 <0.01 - <1.0 289 > 10 <0.01 <0.01 - > 10 <0.01 <1.0 <1.0 290 4.32 <0.01 <0.01 0,032 4,51 <0.01 <1.0 <1.0 291 4.43 <0.01 <0.01 0,036 4,51 <0.01 <1.0 <1.0 298 > 100 - - - - - - -

As is clear from the data of Tables 3 and 4, most indanone derivatives of the present invention exhibit low cytotoxicity, since they have high values of CC _50. In addition, it was found that most of the indanone derivatives of the present invention quite well inhibit coxsackie viruses, polio-, rhinoviruses, since their EC ₅₀ values were 0.01 μg / ml or less.

Accordingly, the indanone derivatives represented by chemical formula 1 of the present invention show low cytotoxicity and high inhibitory activity against a wide range of picornaviruses and, thus, can be used in a pharmaceutical composition for the prevention or treatment of diseases caused by picornavirus.

<EXPERIMENTAL EXAMPLE 2> Determination of antiviral activity against picornaviruses to reduce multicyclic cytopathic effect (CPE)

Test compounds were evaluated for activity against picornaviruses using a multicyclic cytopathic effect (CPE) reduction assay. Antiviral activity was first determined using a CPE reduction assay based on MTS [3- (4,5-dimethylthiazol-2-yl) -5- (3-carboxymethoxyphenyl) -2- (4-sulfophenyl) -2H-tetrazolium].

For this, cells grown to confluency in 96-well plates were infected with 100 to 50% doses of cell culture infection (CCID ₅₀ ) with the virus. After adsorption, 2 hours at 37 ° C, the virus was removed and serial dilutions of the compounds were added. Cultures were further incubated at 37 ° C for 3 days until complete CPE was observed in the infected and untreated virus control (VC). After removing the medium, 90 μl of culture medium and 10 μl of MTS-phenazine methosulfate (Promega, Leiden, Netherlands) were added to each well. After incubation for 2 hours at 37 ° C, the optical density (OD) was recorded in each well at 498 nm in a microplate reader.

CPE values for evaluating antiviral activity were calculated using the following mathematical formula 3:

[Mathematical formula 3]

The CPE values for cytotoxicity assessment were calculated using the following mathematical formula 4:

[Mathematical formula 4]

In formulas 3 and 4

OD _CC corresponds to the OD of uninfected and untreated parent cell cultures,

OD _VC stands for OD of infected and untreated control cell cultures,

OD _{virus + compound} denotes OD cultures of virus infected cells treated with a given concentration of the compound, and

OD _control refers to OD wells with addition of cell culture medium only.

A 50% effective concentration (EC ₅₀ ) and a 50% cytotoxic concentration (CC ₅₀ ) were defined as the concentrations of the compound that provide 50% protection against virus-induced CPE and which kill 50% of the cells, respectively, and were calculated using logarithmic interpolation.

CC ₅₀ and EC _{50 of} some compounds for various viruses are shown in table 5 below.

TABLE 5 Etc. 10 Etc. 46 Etc. 66 CC ₅₀ [μm] > 100 > 100 > 100 Coxsackie B3 ^with EC ₅₀ [μM] 0.021 ± 0.0072 0.0026 ± 0.0012 0.0033 ± 0.0013 Coxsackie A16 ^d EC ₅₀ [μm] 0.090 ± 0.035 - - Coxsackie A9 ^f EC ₅₀ [μM] - 0.0017 ± 0.000037 0.0083 ± 0.00043 Coxsackie A21 ^d EC ₅₀ [μm] 1.1 ± 0.58 - - Entero 71 ^e EC ₅₀ [μM] 0.012 ± 0.0020 0.0031 ± 0.00034 0.025 ± 0.00092 Echo 9 ^d EC ₅₀ [μm] 0.025 ± 0.0057 0.0035 ± 0.00057 - Echo 11 ^f EC ₅₀ [μM] 0.021 ± 0.083 0.0023 ± 0.00088 0.0072 ± 0.00018 Polio 1 ^f EC ₅₀ [μM] 0.75 ± 0.37 0.068 ± 0.0072 0.69 ± 0.17 Polio 2 ^f EC ₅₀ [μM] 0.36 ± 0.15 0.018 ± 0.0019 0.23 ± 0.020 Polio 3 ^f EC ₅₀ [μM] 1.0 ± 0.57 0.043 ± 0.017 0.58 ± 0.0069

Reno 2 ^g EC ₅₀ [μM] > 50 > 10 5.9 ± 0.25 Reno 9 ^g EC ₅₀ [μM] > 50 3.5 ± 0.15 2.3 ± 0.70 Reno 15 ^g EC ₅₀ [μM] > 50 2.8 ± 0.26 4.6 ± 1.3 Reno 29 ^g EC ₅₀ [μM] > 50 4.6 ± 0.72 6.4 ± 0.83 Reno 39 ^g EC ₅₀ [μM] > 50 3.0 ± 0.17 1.8 ± 0.37 Reno 41 ^g EC ₅₀ [μM] 8.8 ± 0.12 0.47 ± 0.036 0.60 ± 0.026 Reno 45 ^g EC ₅₀ [μM] 3.4 ± 1.5 <0,078 1.7 ± 0.46 Reno 59 ^g EC ₅₀ [μM] - - > 10 Reno 63 ^g EC ₅₀ [μM] > 50 8.5 ± 0.13 > 10 Reno 85 ^g EC ₅₀ [μM] > 50 6.2 ± 0.70 > 5.8 Reno 89 ^g EC ₅₀ [μM] > 50 0.34 ± 0.86 0.63 ± 0.023 Reno 14 ^g EC ₅₀ [μM] - <0.01 - Reno 42 ^g EC ₅₀ [μM] > 50 - 0.15 ± 0.023 Reno 70 ^g EC ₅₀ [μM] 2.4 ± 0.36 > 0,078 0.057 ± 0.017 Reno 72 ^g EC ₅₀ [μM] 5.3 ± 1.2 - 0.13 ± 0.069 Reno 86 ^g EC ₅₀ [μM] 8 ± 2.9 - 0.070 ± 0.0066

In Table 5, the superscript ^c denotes incubation at 37 ° C in Vero cells, the superscript ^d denotes incubation at 37 ° C in MRC-5 cells, the superscript ^e denotes incubation at 37 ° C in RD cells, the superscript ^f denotes incubation at 37 ° C in BGM cells, a superscript ^g denotes incubation at 37 ° C in HeLa cells, and a superscript ⁱ denotes 100% inhibition of viral replication with compounds of 0.078 μM or more.

As can be seen from table 5, the indanone derivatives of the present invention have low cytotoxicity, since their CC ₅₀ was measured at 100 μM or higher. In addition, it was found that indanone derivatives have an EC ₅₀ value of 1.1 μM or less with respect to the Coxsackie viruses B3, A16, A9 and A21. In particular, high antiviral activity was found for the compound of Example 46 with a low EC ₅₀ value of 0.0017 μM.

As for enterovirus 71, the indanone derivatives of the present invention showed an EC ₅₀ of 0.025 μM or less. In particular, high antiviral activity was found in the compound of Example 46 with a low EC ₅₀ value of 0.0031 μM.

The indanone derivatives of the invention showed an EC ₅₀ value of 0.025 μM or less against echovirus 9 and echovirus 11, while the maximum antiviral activity was found for the compound of Example 46, as shown by an EC ₅₀ value of 0.0035 μM.

In the case of polioviruses 1, 2 and 3, the EC ₅₀ values of the indanone derivatives of the present invention were measured as 1.0 μM or less. In particular, a high antiviral activity was found for the compound of Example 46 with a low EC ₅₀ value of only 0.068 μM.

In addition, the indanone derivatives of the invention inhibit rhinoviruses fairly well. For example, the compound of Example 46 has an EC ₅₀ value of 0.078 μM or less for rhinoviruses 45 and 70.

Thus, the indanone derivatives of the present invention have low cytotoxicity and exhibit excellent antiviral activity against picornaviruses, including coxsacki viruses, entero-, echo-, polio- and rhinoviruses, therefore, they can be used to prevent or treat respiratory, cardiovascular and diseases picornavirus-induced nervous systems, including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus u, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, influenza, vesicular pharyngitis, foot and mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis and otitis media.

<EXAMPLE OF COMPOSITION 1> Preparation of pharmaceutical formulations

<1-1> Production of powder

Derived indanone with the chemical formula 1: 2 g

Lactose: 1 g

The above ingredients were mixed and placed in a sealed bag to obtain a powdery agent.

<1-2> Getting the pill

Derived indanone with the chemical formula 1: 100 mg

Corn Starch: 100 mg

Lactose: 100 mg

Magnesium Stearate: 2 mg

These ingredients were mixed and tableted using a conventional tabletting method.

<1-3> Capsule Production

Derived indanone with the chemical formula 1: 100 mg

Corn Starch: 100 mg

Lactose: 100 mg

Magnesium Stearate: 2 mg

These ingredients were mixed and placed in gelatin capsules using conventional capsule preparation methods.

<1-4> Receiving an injection

Derived indanone with the chemical formula 1: 10 μg / ml

Diluted hydrochloric acid BP: up to pH 3.5

BP Sodium Chloride Injection: Maximum 1 ml

The indanone derivative of the present invention was dissolved in a suitable volume of sodium chloride BP for injection. The pH of the resulting solution was adjusted to pH 3.5 using pars. HCl BP and then the volume was adjusted using sodium chloride BP for injection and the solution was completely mixed. The solution was then filled with a 5 ml type 1 ampoule made of clear glass. The space in the upper part was sealed by melting the glass. The solution contained in the ampoule was autoclaved at 120 ° C for 15 minutes or more to sterilize, and thus receiving an injection.

INDUSTRIAL APPLICABILITY

Having excellent inhibitory activity against picornaviruses, including coxsackie viruses, entero-, echo-, polio- and rhinoviruses, as well as having low cytotoxicity, as described above, the indanone derivative of chemical formula 1 may be useful as an active ingredient in the pharmaceutical composition for the prevention or treatment of viral disease, including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus, hepatitis A, myositis, m okardita, pancreatitis, diabetes, epidemic myalgia, encephalitis, influenza, foot and mouth disease and vesicular pharyngitis.

Claims (17)

1. The derivative of indanone represented by the following formula 1, its pharmaceutically acceptable salt or its optical isomer:
[Formula 1]

Where
A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of —H, halogen, —OH, C ₁ –C ₁₀ alkoxy, linear or branched C ₁ –C ₁₀ alkyl, unsubstituted or substituted with —OH or methoxyphenylalkyl of a 5-7 membered heterocycloalkyl, C ₆ -C ₁₂ aryl, -O (C = O) R ¹ , - (C = O) R ¹ , - (C = O) OR ¹ , -O (C = O ) OR ¹ , -NO ₂ , -NR ¹ R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (SO ₂ ) R ² ;
D is —OH, halogen, linear or branched C ₁ -C ₁₀ alkyl unsubstituted or substituted by phenyl C ₁ -C ₁₀ alkoxy, —O (CH ₂ ) nOH, —O (C = O) R ¹ , —O ( C = O) OR ¹ , —O (C = O) NR ¹ R ² , —NR ¹ (O) R ² , —NR ¹ (C = O) R ² ;
E represents halogen, —OH, —CN, —N = C = O, —N ₃ , C ₁ -C ₁₀ alkoxy, —O (C = O) R ¹ , —O (C = O) OR ¹ , - O (C = O) NR ¹ R ² , -NR ¹ R ² , -NR ¹ (C = O) R ² , -NR ¹ (C = O) OR ² , -NR ¹ (C = O) NR ¹ R ² , -NR ¹ (C = O) NR ² OR ³ , -NR ¹ (SO ₂ ) R ² , -NR ¹ (C = S) NR ¹ R ² , -NR ¹ (P = O) (OR ² ) ₂ or

G ¹ , G ² , G ³ and G ^{4 are} independently or optionally selected from the group consisting of —H, halogen, C ₁ -C ₁₀ alkoxy, linear or branched C ₁ -C ₂₀ alkyl, C ₆ -C ₁₂ aryl, - O (C = O) R ¹ , - (C = O) OR ¹ , -NO ₂ , where two or more adjacent substituents G ¹ , G ² , G ³ and G ⁴ together can form a ring;
X represents hydrogen, oxygen, hydroxy, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkylene, = N-NR ¹ R ² , -NR ¹ -OR ² or = N-OR ¹ ;
Y represents —O—, —NH— or - (NR ⁵ ) -;
R ⁵ represents - (C = O) H, - (C = O) OH, - (C = O) R ¹ , - (C = S) R ¹ or - (C = O) OR ¹ ;
Z represents C or N;
R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen, linear or branched C ₁ -C ₁₀ alkyl, unsubstituted or phenyl substituted linear or branched C ₁ -C ₁₀ alkenyl, C ₃ -C ₇ cycloalkyl, C ₃ - C ₇ heterocycloalkyl, C ₆ -C ₁₂ aryl or 5-14 membered heteroaryl;
where heterocycloalkyl may be substituted by one or more oxygen atoms via a double bond,
aryl is mono- or bicyclic and may have one or more substituents selected from the group consisting of halogen, —CN, phenyl, linear or branched C ₁ -C ₆ alkyl, R ⁵ and C ₁ -C ₆ alkoxy,
heteroaryl is mono-, bi- or tricyclic and may have one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, = O or —O, linear or branched C ₁ —C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,
linear or branched alkyl may be unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, halogen, 5-7 membered heteroaryl and NHBoc,
phenyl may be substituted by one or more substituents selected from the group consisting of halogen, phenyl or phenyl-substituted C ₁ -C ₆ alkoxy,
heterocycloalkyl or heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S,
halogen is F, Cl, Br or I,
n is an integer from 1 to 10, and

denotes a single or double bond. 2. The derivative of indanone, its pharmaceutically acceptable salt or its optical isomer according to claim 1, where
A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of —H, C ₁ -C ₅ alkoxy, linear or branched C ₁ -C ₅ alkyl, unsubstituted or substituted with —OH or methoxyphenylalkyl 5-7 a-membered heterocycloalkyl, C ₆ -C ₁₂ aryl, -NO ₂ and -NR ¹ R ² ;
D is —OH, halogen, linear or branched C ₁ -C ₅ alkyl or unsubstituted or substituted with phenyl C ₁ -C ₅ alkoxy;
E represents halogen, —OH, C ₁ -C ₅ alkoxy;
G ¹ , G ² , G ³ and G ^{4 are} independently or optionally selected from the group consisting of —H, C ₁ -C ₅ alkoxy and linear or branched C ₁ -C ₁₆ alkyl;
X represents oxygen, hydroxyl or linear or branched C ₁ -C ₅ alkyl;
Y represents —O—;
Z represents C or N;
R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen, linear or branched C ₁ -C ₇ alkyl, C ₃ -C ₇ heterocycloalkyl, C ₆ -C ₁₂ aryl or 5-14 membered heteroaryl;
aryl is mono- or bicyclic and may have one or more substituents selected from the group consisting of halogen, phenyl, linear or branched C ₁ -C ₃ alkyl and C ₁ -C ₃ alkoxy,
heteroaryl is mono-, bi- or tricyclic and may have one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, ═O or —O, linear or branched C ₁ —C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,
linear or branched alkyl may be unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, halogen and 5-7 membered heteroaryl,
phenyl may be substituted by one or more substituents selected from the group consisting of halogen and phenyl,
heterocycloalkyl or heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S,
halogen is F or Cl, and

denotes a single or double bond. 3. The derivative of indanone, its pharmaceutically acceptable salt or its optical isomer according to claim 1, where
A ¹ , A ² , A ³ and A ^{4 are} independently or optionally selected from the group consisting of —H and —NR ¹ R ² ;
D represents —OH;
E represents —OH or —NR ¹ (C = O) R ² ;
G ¹ , G ² , G ³ and G ⁴ independently or optionally are —H or linear or branched C ₁ -C ₁₅ alkyl;
X represents oxygen;
Y represents —O—;
Z represents C;
R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or 5-14 membered heteroaryl;
where the 5-14 membered heteroaryl is monocyclic, bicyclic or tricyclic and may be substituted by one or more substituents selected from the group consisting of halogen, —OH, —NO ₂ , —NH ₂ , —CN, ═O or —O, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl,
phenyl may be substituted by one or more substituents selected from the group consisting of halogen and phenyl,
heteroaryl contains at least one heteroatom selected from the group consisting of N, O and S, and
halogen is F or Cl, and

denotes a double bond. 4. The derivative of indanone, its pharmaceutically acceptable salt or its optical isomer according to claim 1, where
A ¹ , A ² and A ³ are —H, and A ⁴ is —NH ₂ ;
D represents —OH;
E represents —NR ¹ (C = O) R ² ;
G ¹ , G ³ and G ⁴ are —H, and G ² is isopropyl;
X represents oxygen;
Y represents —O—;
Z represents C;
R ¹ represents hydrogen and R ² represents a 5-14 membered heteroaryl;
where heteroaryl is furan, benzofuran, pyridine, pyrazolopyridine, pyrimidine, pyrazolopyrimidine, pyrazine, thiophene, quinoline, isoquinoline, triazole, thiazole, indole, pyrazole, indazole, tetrazole, benzotriazole, chromene, pyranesole, pyrrole, pyrozole, pyrrole cinnoline, imidazole, benzoimidazole, acridine, imidazopyridine, imidazopyrimidine, quinoxaline, pyridazine, tetrazolopiridin, triazolopyridine, triazolopyrimidine, or indolizine and may be substituted with one or more substituents selected from the group consisting of halogen, -OH, -NO _2, -NH ₂ , —CN, ═O or —O, linear or branched C ₁ -C ₁₀ alkyl, linear or branched C ₁ -C ₁₀ alkoxy and phenyl, and
halogen is F or Cl, and

denotes a double bond. 5. The derivative of indanone, its pharmaceutically acceptable salt or its optical isomer, where the derivative of indanone is selected from the group consisting of:
1) 4b, 9b-dihydroxy-7-methyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
3) ethyl 2- (4b, 9b-dihydroxy-6-methoxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-8-yl) acetate;
4) 4b, 9b-dihydroxy-7,8-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
6) 8-fluoro-4b, 9b-dihydroxy-4b, 9b-dihydro-10H-indeno [1,2-b] benzofuran-10-one;
7) 4b, 9b-dihydroxy-7-methoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
8) 6,7-dichloro-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
9) 7-ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
10) 4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
11) 7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;
13) 4b, 9b-dihydroxy-6-phenyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
14) 4b, 9b-dihydroxy-8-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
17) 4b, 9b-dihydroxy-8-propyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
18) 8-ethyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
19) 8-sec-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
20) 8-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
21) 6-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
22) 4b, 9b-dihydroxy-7,8,9-trimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
23) 4b, 9b-dihydroxy-8-tert-pentyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
24) 6,8-di-tert-butyl-4b, 9b-dihydroxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
25) 6,8-di-tert-butyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;
26) 4b, 9b-dihydroxy-8-nonyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
27) 4b, 9b-dihydroxy-8-pentadecyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
28) 6,8-bis- (1,1-dimethylpropyl) -4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
29) isopropyl-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;
30) 5a, 10a-dihydroxy-2,3,5a, 10a-tetrahydro-diindeno [1,2-b: 5 ′, 6′-d] furan-10 (1H) -one;
31) 6b, 11b-dihydroxy-1,2,3,4,6b, 11b-hexahydro-12-oxa-benzo [4,5] pentaleno [2,1-a] naphthalen-7-one;
32) 4b, 9b-dihydroxy-7-isopropyl-2-methoxy-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
33) 7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis (2,2-dimethylpropanoate);
34) (2E, 2′E) -7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl bis (3- phenylacrylate);
35) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylacrylate;
36) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl-furan-2-carboxylatefuran-2-carboxylic acid ;
37) diethyl-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl dicarbonate;
38) ethyl 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate;
40) 9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yldiethylcarbamate;
41) 4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yldiethylcarbamate;
42) 2,3-difluoro-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
43) 1,4b, 9b-trihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
44) 4b, 9b-dihydroxy-7-isopropyl-1H-cyclopenta [b] naphthalene [1,2-b] furan-10 (9bH) -one;
45) 9b-hydroxy-7-isopropyl-4b-methoxy-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
46) 1-amino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
47) 1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;
48) N- (4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide;
49) methyl 4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;
50) 1-amino-7-ethyl-4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
51) 7-ethyl-4b, 9b-dihydroxy-1-nitro-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
52) 7-ethyl-2,4b, 9b-trihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
53) 4b-acetoxy-1-amino-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;
54) 4b-acetoxy-7-isopropyl-1-methanesulfonylamino-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;
55) 1- (4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) -3-isopropylurea;
56) N- (9b-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide;
57) N, N ′ - (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1,9b-diyl) diacetamide;
58) N- (7-amino-2-hydroxy-2- (4-isopropyl-2-hydroxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-4-yl) acetamide;
59) N- (2-amino-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide ;
60) 1-amino-4b, 9b-dihydroxy-7-isopropyl-2-nitro-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
61) 1,4-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
62) 1,2-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
63) 2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-yldimethylcarbamate;
64) 4b, 9b-dihydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
65) 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
66) N- (4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) acetamide;
67) 9b-hexylamino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
68) 9b-amino-4b-hydroxy-6,8-diisopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
69) 4b-hydroxy-9b-isocyanato-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
70) methyl - ((4b, 9b) -4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-9bH-indeno [1,2-b] benzofuran-9b-yl) carbamate;
71) (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) pentanoic acid amide;
72) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) isobutylamide;
73) N- (1-amino-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide;
74) N- (9b-hydroxy-6,8-diisopropyl-10-oxo-9b, 10-dihydro-5-oxa-indeno [2,1-a] inden-4b-yl) acetamide;
75) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) -N-methylacetamide;
76) 1- (4b-hydroxy-7-isopropyl-1-nitro-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) -3-isopropylurea;
77) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) isobutylamide;
78) (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxa-indeno [2,1-a] inden-9b-yl) pentanoic acid amide;
79) 9b-hydroxy-4b- (2-hydroxyethoxy) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
80) 4b, 9b-dihydroxy-7-isopropyl-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
81) 4b, 9b-dihydroxy-7-isopropyl-2,3-dimethoxy-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
82) 4b, 9b-dihydroxy-7-isopropyl-2,3-dimethyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
83) a mixture of 6: 4 (4bS, 9bS) -2-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one and ( 4bS, 9bS) -3-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
84) indeno [2,1-a] inden-4b, 9b (5H, 10H) -diol;
85) isopropyl- (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate;
86) ethyl (4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamate;
87) N, N ′ - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1, 9b-diyl) diacetamide;
88) O-methyloxy 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
89) 9b-butyrylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of butyric acid;
90) [2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxoindan-2-yl] octanoic acid amide;
91) 9b-hexanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl hexanoic acid ester;
92) 9b-heptanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl heptanoic acid ester;
93) N - ((4bS, 9bS) -1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) octanamide ;
94) (4bR, 9bS) -1-amino-7-isopropyl-10-oxo-9b-propionamido-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpropionate;
95) (4bR, 9bS) -1-amino-9b-butyramido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylbutyrate;
96) 1-amino-7-isopropyl-10-oxo-9b-pentanamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpentanoate;
97) 1-amino-9b-hexanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylhexanoate;
98) (4bS, 9bS) -4b-hydroxy-7-isopropyl-9b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
99) 1-amino-9b-heptanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylheptanoate;
100) 1 - ((4bS, 9bS) -7-isopropyl-4b-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea;
101) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylurea;
102) 1-ethyl-3 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea ;
103) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxyurea;
104) 5-acetyl-4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
105) 4b, 9b-dihydroxy-7,8-dimethyl-5-propionyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
106) 4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
107) 5-acetyl-7.8-dimethyl-10-oxo-4b, 5.9b, 10-tetrahydroindeno [1,2-b] indole-4b, 9b-diyl diacetate;
108) 5-acetyl-9b-amino-4b-hydroxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
109) N- (9b-amino-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl) acetamide ;
110) 1.9b-bis-acetylamino-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl acetic acid ester;
111) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;
112) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpentanoate;
113) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;
114) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) pivalamide;
115) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylbutyl carbonate;
116) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ethyl ethyl carbonate;
117) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl pivalate;
118) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylmethylcarbamate;
119) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) diacetamide;
120) 4b- (benzyloxy) -9b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
121) 9b-acetylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of phenyl carbonic ester;
122) O- (9b-azido-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) phenylthiocarbamic acid ester;
123) ethyl 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate;
124) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) dipropionamide;
125) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) bis (2-methylpropanamide);
126) 4b, 9b-dihydroxy-7-isopropyl-4bH-benzofuro [2 ′, 3 ′: 3,4] cyclopenta [1,2-b] pyridin-10 (9bH) -one;
127) 10-hydroxy-7-isopropyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl diacetate;
128) O-methyl oxime of 9b-hydroxy-7-isopropyl-4b- (methoxyamino) -4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
129) 7-isopropyl-4b-methoxy-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-ol;
130) O-methyloxime of 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
131) mixtures of 1-bromo and 4-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
132) 1- (benzylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
133) 1- (ethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
134) 9b-hydroxy-7-isopropyl-4b-methyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
135) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
136) 7-isopropyl-10-methyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diol;
137) N- (1-bromo-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide;
138) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethoxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
139) 4b, 9b-dihydroxy-7-isopropyl-2-piperidinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
140) 4b, 9b-dihydroxy-7-isopropyl-2-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
141) 4b, 9b-dihydroxy-7-isopropyl-1-piperidinyl-4bH-benzo [d] indeno- [1,2-b] furan-10 (9bH) -one;
142) 4b, 9b-dihydroxy-7-isopropyl-1-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
143) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) propionamide;
144) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) butyramide;
145) 4b, 9b-dihydroxy-5-isobutyryl-7-isopropyl-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
146) 4b, 9b-dihydroxy-7-isopropyl-2- (hydroxypiperidinyl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
147) 4b, 9b-dihydroxy-1- (4-hydroxypiperidin-1-yl) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
148) 4b, 9b-dihydroxy-7-isopropyl-2- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - she;
149) 4b, 9b-dihydroxy-7-isopropyl-1- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - she;
150) 2- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
151) 1- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
152) 10-hydrazono-7-isopropyl-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diol;
153) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide;
154) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxybenzamide;
155) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chlorobenzamide;
156) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-nitrobenzamide;
157) 1-amino-4b, 9b-dihydroxy-6,8-diisopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
158) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) cyclopropanecarboxamide;
159) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (4-methoxyphenyl) thiourea;
160) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (phenyl) thiourea;
161) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) thiophene-2-carboxamide;
162) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-methoxyphenyl urea
163) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-butylurea;
164) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-fluorophenyl urea
165) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (tert-butyl urea
166) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
167) N- (1-formamido-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide;
168) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;
169) diethyl- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) phosphoamidate;
170) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-cyanobenzamide;
171) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-naphthamide;
172) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - [1,1′- biphenyl] -4-carboxamide;
173) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- ethylureas;
174) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) tetrahydrofuran-2 β-carboxamide;
175) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,2,2- trifluoroacetamide;
176) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1, 1,1-trifluoromethanesulfonamide;
177) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
178) 1,1,1-trifluoro-N- (4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;
179) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-phenylacetamide;
180) (E) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (3,4-dichlorophenyl) acrylamide;
181) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4- (benzyloxy) benzamide ;
182) 2 - ([1,1′-biphenyl] -4-yl) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) acetamide;
183) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxybenzamide;
184) tert-butyl- (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino ) -1-oxopropan-2-ylcarbamate;
185) tert-butyl- (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino ) -1-oxo-3-phenylpropan-2-ylcarbamate;
186) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- methylbenzamide;
187) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzamide;
188) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methylbenzamide;
189) methyl 4- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamoyl) benzoate ;
190) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chlorobenzamide;
191) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3,5-dimethylbenzamide;
192) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,4,6- trichlorobenzamide;
193) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- fluoroacetamide;
194) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- chloroacetamide;
195) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2, 2-dichloroacetamide;
196) 1-amino-9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 ( 9bH) -one;
197) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;
198) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
199) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isonicotinamide;
200) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazine-2-carboxamide;
201) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
202) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide;
203) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide;
204) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran-2 β-carboxamide;
205) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzofuran-2-carboxamide;
206) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylthiazole-5- carboxamide;
207) (4R) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2- oxothiazolidine-4-carboxamide;
208) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-2-carboxamide;
209) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-3-carboxamide;
210) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
211) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-phenyl-5- (trifluoromethyl) - 1H-pyrazole-4-carboxamide;
212) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indazole-3-carboxamide;
213) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazol-1-yl) acetamide;
214) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-3-carboxamide;
215) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide;
216) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylthiophen-2- carboxamide;
217) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxythiophen-3- carboxamide;
218) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;
219) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrimidine-4-carboxamide;
220) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazole -5-yl) acetamide;
221) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] [1,2,3] triazole-5-carboxamide;
222) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-1,2, 4-triazole-3-carboxamide;
223) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5-nitrothiophen-2- carboxamide;
224) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2,6-dioxo 1,2,3,6-tetrahydropyrimidine-4-carboxamide;
225) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- chromene-3-carboxamide;
226) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- pyran-5-carboxamide;
227) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;
228) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (2-chloro -6-fluorophenyl) -5-methylisoxazole-4-carboxamide;
229) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-phenyl-1H-pyrazol-5- carboxamide;
230) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
231) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-oxo-2- (thiophen-2-yl) acetamide;
232) 5-amino-N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2 β-carboxamide;
233) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2- carboxamide;
234) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxyisonicotinamide;
235) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b ] thiophene-2-carboxamide;
236) 3- (2,6-dichlorophenyl) -N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) -5-methylisoxazole-4-carboxamide;
237) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -9H- xanthene-9-carboxamide;
238) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4 β-carboxamide;
239) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4-carboxamide;
240) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-5-carboxamide;
241) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridin-9 β-carboxamide;
242) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- nitro-1H-pyrazole-3-carboxamide;
243) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methyl picolinamide;
244) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- (trifluoromethyl) picolinamide;
245) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5- cyanopicolinamide;
246) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- chloropicolinamide;
247) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methoxyquinoline-2-carboxamide;
248) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isoquinoline-3-carboxamide;
249) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methylisonicotinamide;
250) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-fluoroisonicotinamide;
251) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloroisonicotinamide;
252) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-2-carboxamide;
253) 2 - ((1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1-oxide ;
254) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chloronicotinamide;
255) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-nicotinamide;
256) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-hydroxynicotinamide;
257) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-hydroxypicolinamide;
258) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylnicotinamide;
259) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylnicotinamide;
260) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
261) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methoxynicotinamide;
262) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide ;
263) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinolin-2 β-carboxamide;
264) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- bromobenzo [b] thiophene-2-carboxamide;
265) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indole-2-carboxamide;
266) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinolin-1 β-carboxamide;
267) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -6-fluoro-4- methoxyquinoline-3-carboxamide;
268) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indole-2-carboxamide;
269) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- fluorobenzo [b] thiophene-2-carboxamide;
270) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- methylbenzo [b] thiophene-2-carboxamide;
271) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,3-dimethyl- 1H-pyrazolo [3,4-b] pyridin-5-carboxamide;
272) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyridine-6-carboxamide;
273) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1,5-a ] pyrimidine-2-carboxamide;
274) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylbenzo [b] thiophene-2-carboxamide;
275) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide;
276) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyridazine-4-carboxamide;
277) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide;
278) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-6-carboxamide;
279) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-8-carboxamide;
280) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylimidazo [1, 2-a] pyridin-2-carboxamide;
281) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methyl [1, 2,4] triazolo [1,5-a] pyrimidine-2-carboxamide;
282) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5,7-dimethylpyrazolo [ 1,5-a] pyrimidine-3-carboxamide;
283) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide;
284) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,6-diisopropyl- 1H-pyrazolo [3,4-b] pyridin-4-carboxamide;
285) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyrimidine-2-carboxamide;
286) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-oxo-1, 2-dihydroisoquinoline-3-carboxamide;
287) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylimidazo [1,5-a] pyridin-1-carboxamide;
288) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2H- indazole-3-carboxamide;
289) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [1, 5-a] pyrimidine-6-carboxamide;
290) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;
291) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-1H- benzo [d] imidazole-2-carboxamide;
292) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-5-carboxamide;
293) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indazole-3-carboxamide;
294) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-5- carboxamide;
295) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-3a, 7a-dihydro-1H-indazole-3-carboxamide;
296) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-4-carboxamide;
297) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-3- carboxamide;
298) tert-butyl- (tert-butoxycarbonylamino) (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) methylene carbamate;
299) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indazole-5- carboxamide;
300) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methyl-1H- pyrazole-5-carboxamide;
301) 1-amino-9b- (furan-2-carboxamido) -7-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-yl furan-2-carboxylate ;
302) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
303) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
304) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
305) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
306) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide; and
307) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrahydrofuran-2-carboxamide. 6. The indanone derivative, its pharmaceutically acceptable salt or its optical isomer according to claim 5, wherein the indanone derivative is selected from the group consisting of:
29) isopropyl-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;
45) 9b-hydroxy-7-isopropyl-4b-methoxy-1-nitro-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
46) 1-amino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
47) 1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diyl diacetate;
49) methyl 4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-ylcarbamate;
50) 1-amino-7-ethyl-4b, 9b-dihydroxy-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
51) 7-ethyl-4b, 9b-dihydroxy-1-nitro-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
52) 7-ethyl-2,4b, 9b-trihydroxy-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
53) 4b-acetoxy-1-amino-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;
54) 4b-acetoxy-7-isopropyl-1-methanesulfonylamino-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl acetic acid ester;
55) 1- (4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) -3-isopropylurea;
56) N- (9b-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide;
57) N, N ′ - (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1,9b-diyl) diacetamide;
58) N- (7-amino-2-hydroxy-2- (4-isopropyl-2-hydroxyphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-4-yl) acetamide;
59) N- (2-amino-4b, 9b-dihydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1-yl) acetamide ;
60) 1-amino-4b, 9b-dihydroxy-7-isopropyl-2-nitro-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
61) 1,4-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
62) 1,2-diamino-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
63) 2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxo-2,3-dihydro-1H-inden-2-yldimethylcarbamate;
65) 9b-amino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxaindeno [2,1-a] inden-10-one;
66) N- (4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) acetamide;
67) 9b-hexylamino-4b-hydroxy-7-isopropyl-4b, 9b-dihydro-5-oxa-indeno [2,1-a] inden-10-one;
70) methyl - ((4b, 9b) -4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-9bH-indeno [1,2-b] benzofuran-9b-yl) carbamate;
71) (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) pentanoic acid amide;
72) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) isobutylamide;
73) N- (1-amino-9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) acetamide;
74) N- (9b-hydroxy-6,8-diisopropyl-10-oxo-9b, 10-dihydro-5-oxa-indeno [2,1-a] inden-4b-yl) acetamide;
75) N- (9b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) -N-methylacetamide;
77) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxaindeno [2,1-a] inden-9b-yl) isobutylamide;
78) (1-amino-4b-hydroxy-7-isopropyl-10-oxo-4b, 10-dihydro-5-oxa-indeno [2,1-a] inden-9b-yl) pentanoic acid amide;
87) N, N ′ - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-1, 9b-diyl) diacetamide;
88) O-methyloxy 4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
89) 9b-butyrylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of butyric acid;
90) [2- (2-hydroxy-4-isopropylphenyl) -1,3-dioxoindan-2-yl] octanoic acid amide;
91) 9b-hexanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl hexanoic acid ester;
92) 9b-heptanoylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl heptanoic acid ester;
93) N - ((4bS, 9bS) -1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) octanamide ;
94) (4bR, 9bS) -1-amino-7-isopropyl-10-oxo-9b-propionamido-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpropionate;
95) (4bR, 9bS) -1-amino-9b-butyramido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylbutyrate;
96) 1-amino-7-isopropyl-10-oxo-9b-pentanamido-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylpentanoate;
97) 1-amino-9b-hexanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylhexanoate;
98) (4bS, 9bS) -4b-hydroxy-7-isopropyl-9b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
99) 1-amino-9b-heptanamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylheptanoate;
100) 1 - ((4bS, 9bS) -7-isopropyl-4b-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea;
101) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylurea;
102) 1-ethyl-3 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) urea ;
103) 1 - ((4bS, 9bS) -4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxyurea;
104) 5-acetyl-4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
105) 4b, 9b-dihydroxy-7,8-dimethyl-5-propionyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
106) 4b, 9b-dihydroxy-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
107) 5-acetyl-7.8-dimethyl-10-oxo-4b, 5.9b, 10-tetrahydroindeno [1,2-b] indole-4b, 9b-diyl diacetate;
108) 5-acetyl-9b-amino-4b-hydroxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
109) N- (9b-amino-4b-hydroxy-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-4bH-5-oxaindeno [2,1-a] inden-1-yl) acetamide ;
110) 1.9b-bis-acetylamino-7-isopropyl-4-nitro-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl acetic acid ester;
111) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;
112) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylpentanoate;
113) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-ylmethyl carbonate;
114) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) pivalamide;
115) 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylbutyl carbonate;
116) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ethyl ethyl carbonate;
117) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl pivalate;
118) 9b-acetamido-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-ylmethylcarbamate;
119) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) diacetamide;
120) 4b- (benzyloxy) -9b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
121) 9b-acetylamino-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl ester of phenyl carbonic ester;
122) O- (9b-azido-7-isopropyl-10-oxo-9b, 10-dihydro-5-oxaindeno [2,1-a] inden-4b-yl) phenylthiocarbamic acid ester;
123) ethyl 9b-acetamido-1-amino-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b-yl carbonate;
124) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) dipropionamide;
125) N, N ′ - (7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl) bis (2-methylpropanamide);
126) 4b, 9b-dihydroxy-7-isopropyl-4bH-benzofuro [2 ′, 3 ′: 3,4] cyclopenta [1,2-b] pyridin-10 (9bH) -one;
127) 10-hydroxy-7-isopropyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diyl diacetate;
128) O-methyl oxime of 9b-hydroxy-7-isopropyl-4b- (methoxyamino) -4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
129) 7-isopropyl-4b-methoxy-10-methylene-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-ol;
130) O-methyloxime of 9b-hydroxy-7-isopropyl-4b-methoxy-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
131) mixtures of 1-bromo and 4-bromo-4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
132) 1- (benzylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
133) 1- (ethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
134) 9b-hydroxy-7-isopropyl-4b-methyl-4bH-indeno [1,2-b] benzofuran-10 (9bH) -one;
135) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethyl-4b, 5-dihydroindeno [1,2-b] indol-10 (9bH) -one;
136) 7-isopropyl-10-methyl-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b, 9b-diol;
137) N- (1-bromo-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) acetamide;
138) 4b, 9b-dihydroxy-5-isobutyryl-7,8-dimethoxy-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
139) 4b, 9b-dihydroxy-7-isopropyl-2-piperidinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
140) 4b, 9b-dihydroxy-7-isopropyl-2-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
141) 4b, 9b-dihydroxy-7-isopropyl-1-piperidinyl-4bH-benzo [d] indeno- [1,2-b] furan-10 (9bH) -one;
142) 4b, 9b-dihydroxy-7-isopropyl-1-morpholinyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
143) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) propionamide;
144) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) butyramide;
145) 4b, 9b-dihydroxy-5-isobutyryl-7-isopropyl-5,9b-dihydro-4bH-indeno [1,2-b] indol-10-one;
146) 4b, 9b-dihydroxy-7-isopropyl-2- (hydroxypiperidinyl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
147) 4b, 9b-dihydroxy-1- (4-hydroxypiperidin-1-yl) -7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
148) 4b, 9b-dihydroxy-7-isopropyl-2- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - she;
149) 4b, 9b-dihydroxy-7-isopropyl-1- (4- (4-methoxybenzyl) piperazin-1-yl) -4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) - she;
150) 2- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
151) 1- (dimethylamino) -4b, 9b-dihydroxy-7-isopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
152) 10-hydrazono-7-isopropyl-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-4b, 9b-diol;
153) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) benzamide;
154) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methoxybenzamide;
155) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chlorobenzamide;
156) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-nitrobenzamide;
157) 1-amino-4b, 9b-dihydroxy-6,8-diisopropyl-4bH-benzo [d] indeno [1,2-b] furan-10 (9bH) -one;
158) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) cyclopropanecarboxamide;
159) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (4-methoxyphenyl) thiourea;
160) 1- (4b-hydroxy-6,8-diisopropyl-1-amino-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) - 3- (phenyl) thiourea;
161) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) thiophene-2-carboxamide;
162) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-methoxyphenyl urea
163) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-butylurea;
164) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (4-fluorophenyl urea
165) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (tert-butyl urea
166) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
167) N- (1-formamido-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acetamide;
168) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;
169) diethyl- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) phosphoamidate;
170) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-cyanobenzamide;
171) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-naphthamide;
172) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) - [1,1′- biphenyl] -4-carboxamide;
173) 1- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- ethylureas;
174) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) tetrahydrofuran-2 β-carboxamide;
175) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,2,2- trifluoroacetamide;
176) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1, 1,1-trifluoromethanesulfonamide;
177) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
178) 1,1,1-trifluoro-N- (4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) methanesulfonamide;
179) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-phenylacetamide;
180) (E) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (3,4-dichlorophenyl) acrylamide;
181) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4- (benzyloxy) benzamide ;
182) 2 - ([1,1′-biphenyl] -4-yl) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1, 2-b] benzofuran-9b-yl) acetamide;
183) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxybenzamide;
184) tert-butyl- (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino ) -1-oxopropan-2-ylcarbamate;
185) tert-butyl- (2R) -1- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino ) -1-oxo-3-phenylpropan-2-ylcarbamate;
186) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- methylbenzamide;
187) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzamide;
188) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methylbenzamide;
189) methyl 4- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylcarbamoyl) benzoate ;
190) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chlorobenzamide;
191) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3,5-dimethylbacksamide;
192) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2,4,6- trichlorobenzamide;
193) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- fluoroacetamide;
194) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- chloroacetamide;
195) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2, 2-dichloroacetamide;
196) 1-amino-9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 ( 9bH) -one;
197) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;
198) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
199) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isonicotinamide;
200) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazine-2-carboxamide;
201) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
202) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide;
203) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide;
204) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran-2 β-carboxamide;
205) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzofuran-2-carboxamide;
206) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylthiazole-5- carboxamide;
207) (4R) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2- oxothiazolidine-4-carboxamide;
208) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-2-carboxamide;
209) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-3-carboxamide;
210) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) formamide;
211) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-phenyl-5- (trifluoromethyl) - 1H-pyrazole-4-carboxamide;
212) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indazole-3-carboxamide;
213) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazol-1-yl) acetamide;
214) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-3-carboxamide;
215) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide;
216) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylthiophen-2- carboxamide;
217) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxythiophen-3- carboxamide;
218) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;
219) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrimidine-4-carboxamide;
220) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazole -5-yl) acetamide;
221) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] [1,2,3] triazole-5-carboxamide;
222) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-1,2, 4-triazole-3-carboxamide;
223) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5-nitrothiophen-2- carboxamide;
224) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2,6-dioxo 1,2,3,6-tetrahydropyrimidine-4-carboxamide;
225) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- chromene-3-carboxamide;
226) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2-oxo-2H- pyran-5-carboxamide;
227) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;
228) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (2-chloro -6-fluorophenyl) -5-methylisoxazole-4-carboxamide;
229) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-phenyl-1H-pyrazol-5- carboxamide;
230) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
231) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-oxo-2- (thiophen-2-yl) acetamide;
232) 5-amino-N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2 β-carboxamide;
233) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2- carboxamide;
234) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxyisonicotinamide;
235) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b ] thiophene-2-carboxamide;
236) 3- (2,6-dichlorophenyl) -N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b -yl) -5-methylisoxazole-4-carboxamide;
237) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -9H- xanthene-9-carboxamide;
238) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4 β-carboxamide;
239) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4-carboxamide;
240) N- (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H-benzo [d] imidazole-5-carboxamide;
241) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridin-9 β-carboxamide;
242) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- nitro-1H-pyrazole-3-carboxamide;
243) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methyl picolinamide;
244) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- (trifluoromethyl) picolinamide;
245) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5- cyanopicolinamide;
246) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- chloropicolinamide;
247) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methoxyquinoline-2-carboxamide;
248) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isoquinoline-3-carboxamide;
249) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methylisonicotinamide;
250) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-fluoroisonicotinamide;
251) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloroisonicotinamide;
252) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-2-carboxamide;
253) 2 - ((1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1-oxide ;
254) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chloronicotinamide;
255) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-nicotinamide;
256) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-hydroxynicotinamide;
257) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-hydroxypicolinamide;
258) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylnicotinamide;
259) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylnicotinamide;
260) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
261) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methoxynicotinamide;
262) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide ;
263) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinolin-2 β-carboxamide;
264) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- bromobenzo [b] thiophene-2-carboxamide;
265) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indole-2-carboxamide;
266) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinolin-1 β-carboxamide;
267) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -6-fluoro-4- methoxyquinoline-3-carboxamide;
268) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indole-2-carboxamide;
269) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- fluorobenzo [b] thiophene-2-carboxamide;
270) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- methylbenzo [b] thiophene-2-carboxamide;
271) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,3-dimethyl- 1H-pyrazolo [3,4-b] pyridin-5-carboxamide;
272) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyridine-6-carboxamide;
273) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1,5-a ] pyrimidine-2-carboxamide;
274) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylbenzo [b] thiophene-2-carboxamide;
275) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide;
276) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyridazine-4-carboxamide;
277) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-6-carboxamide;
278) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-6-carboxamide;
279) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-8-carboxamide;
280) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylimidazo [1, 2-a] pyridin-2-carboxamide;
281) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methyl [1, 2,4] triazolo [1,5-a] pyrimidine-2-carboxamide;
282) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5,7-dimethylpyrazolo [ 1,5-a] pyrimidine-3-carboxamide;
283) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide;
284) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,6-diisopropyl- 1H-pyrazolo [3,4-b] pyridin-4-carboxamide;
285) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyrimidine-2-carboxamide;
286) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-oxo-1, 2-dihydroisoquinoline-3-carboxamide;
287) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylimidazo [1,5-a] pyridin-1-carboxamide;
288) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2H- indazole-3-carboxamide;
289) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [1, 5-a] pyrimidine-6-carboxamide;
290) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;
291) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-1H- benzo [d] imidazole-2-carboxamide;
292) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-5-carboxamide;
293) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indazole-3-carboxamide;
294) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-5- carboxamide;
295) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-3a, 7a-dihydro-1H-indazole-3-carboxamide;
296) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-4-carboxamide;
297) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-3- carboxamide;
298) tert-butyl- (tert-butoxycarbonylamino) (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) methylene carbamate;
299) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indazole-5- carboxamide;
300) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methyl-1H- pyrazole-5-carboxamide;
301) 1-amino-9b- (furan-2-carboxamido) -7-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-yl furan-2-carboxylate ;
302) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
303) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
304) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
305) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
306) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide; and
307) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrahydrofuran-2-carboxamide. 7. The indanone derivative, a pharmaceutically acceptable salt thereof or its optical isomer according to claim 5, wherein the indanone derivative is selected from the group consisting of:
196) 1-amino-9b- (4-butyl-1H-1,2,3-triazol-1-yl) -4b-hydroxy-7-isopropyl-4bH-indeno [1,2-b] benzofuran-10 ( 9bH) -one;
197) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) picolinamide;
198) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
199) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isonicotinamide;
200) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazine-2-carboxamide;
201) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
202) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-8-carboxamide;
203) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide;
204) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzofuran-2 β-carboxamide;
205) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylbenzofuran-2-carboxamide;
206) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylthiazole-5- carboxamide;
207) (4R) -N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2- oxothiazolidine-4-carboxamide;
212) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indazole-3-carboxamide;
213) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2- (1H-tetrazol-1-yl) acetamide;
214) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-3-carboxamide;
215) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide;
216) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylthiophen-2- carboxamide;
217) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxythiophen-3- carboxamide;
228) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3- (2-chloro -6-fluorophenyl) -5-methylisooxazole-4-carboxamide;
231) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-oxo-2- (thiophen-2-yl) acetamide;
232) 5-amino-N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2 β-carboxamide;
233) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2- carboxamide;
234) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methoxyisonicotinamide;
235) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) benzo [b ] thiophene-2-carboxamide;
237) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -9H- xanthene-9-carboxamide;
238) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) cinnolin-4 β-carboxamide;
241) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) acridin-9 β-carboxamide;
242) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- nitro-1H-pyrazole-3-carboxamide;
243) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methyl picolinamide;
244) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- (trifluoromethyl) picolinamide;
245) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -5- cyanopicolinamide;
246) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- chloropicolinamide;
247) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -4- methoxyquinoline-2-carboxamide;
248) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) isoquinoline-3-carboxamide;
249) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -2-methylisonicotinamide;
250) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-fluoroisonicotinamide;
251) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloroisonicotinamide;
252) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-2-carboxamide;
253) 2 - ((1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) carbamoyl) pyridine 1-oxide ;
254) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-chloronicotinamide;
255) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-nicotinamide;
256) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-hydroxynicotinamide;
257) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-hydroxypicolinamide;
258) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -4-methylnicotinamide;
259) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methylnicotinamide;
260) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
261) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-methoxynicotinamide;
262) N- (1-amino-4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-6-carboxamide ;
263) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) quinolin-2 β-carboxamide;
264) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- bromobenzo [b] thiophene-2-carboxamide;
265) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -1H- indole-2-carboxamide;
266) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) isoquinolin-1 β-carboxamide;
267) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -6-fluoro-4- methoxyquinoline-3-carboxamide;
268) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indole-2-carboxamide;
269) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- fluorobenzo [b] thiophene-2-carboxamide;
270) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-chloro-6- methylbenzo [b] thiophene-2-carboxamide;
271) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,3-dimethyl- 1H-pyrazolo [3,4-b] pyridin-5-carboxamide;
272) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyridine-6-carboxamide;
273) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyrazolo [1,5-a ] pyrimidine-2-carboxamide;
274) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methylbenzo [b] thiophene-2-carboxamide;
275) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-2-carboxamide;
276) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) pyridazine-4-carboxamide;
277) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoxaline-b-carboxamide;
278) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-6-carboxamide;
279) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-8-carboxamide;
280) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylimidazo [1, 2-a] pyridin-2-carboxamide;
281) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methyl [1, 2,4] triazolo [1,5-a] pyrimidine-2-carboxamide;
282) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5,7-dimethylpyrazolo [ 1,5-a] pyrimidin-3-carboxamide;
283) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) indolysin-2-carboxamide;
284) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1,6-diisopropyl- 1H-pyrazolo [3,4-b] pyridin-4-carboxamide;
285) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) imidazo [1,2-a ] pyrimidine-2-carboxamide;
286) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-oxo-1, 2-dihydroisoquinoline-3-carboxamide;
287) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -3- methylimidazo [1,5-a] pyridin-1-carboxamide;
288) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-yl) -2H- indazole-3-carboxamide;
289) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -7-methylpyrazolo [1, 5-a] pyrimidine-6-carboxamide;
290) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-benzo [d] imidazole-2-carboxamide;
291) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -5-fluoro-1H- benzo [d] imidazole-2-carboxamide;
292) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrazolo [1,5-a ] pyridine-5-carboxamide;
293) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- indazole-3-carboxamide;
294) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indole-5- carboxamide;
295) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-3a, 7a-dihydro-1H-indazole-3-carboxamide;
296) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1-methyl-1H- imidazole-4-carboxamide;
297) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-3- carboxamide;
298) tert-butyl- (tert-butoxycarbonylamino) (4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo [d] indeno [1,2-b] furan-9b-ylamino) methylene carbamate;
299) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-indazole-5- carboxamide;
300) N- (1-amino-4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -3-methyl-1H- pyrazole-5-carboxamide;
301) 1-amino-9b- (furan-2-carboxamido) -7-methoxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-4b-yl furan-2-carboxylate ;
302) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) nicotinamide;
303) N- (4b-hydroxy-7,8-dimethyl-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
304) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) -1H-pyrrole-2-carboxamide;
305) N- (6-ethyl-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) furan-2-carboxamide;
306) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) quinoline-4-carboxamide; and
307) N- (8-chloro-4b-hydroxy-10-oxo-9b, 10-dihydro-4bH-indeno [1,2-b] benzofuran-9b-yl) tetrahydrofuran-2-carboxamide. 8. A method of obtaining a derivative of indanone according to claim 1, including:
acylating or alkylating a compound of formula 1 with a base in a solvent to obtain a compound of formula 1a (step 1), as shown in the following reaction scheme 1:
[Reaction scheme 1]

Where
the compound of formula 1a is a derivative of formula 1 according to claim 1, its pharmaceutically acceptable salt or its optical isomer,
A ¹ , A ² , A ³ , A ⁴ , G ¹ , G ² , G ³ , G ⁴ , and Z are as defined in chemical formula 1 according to claim 1, and
X represents O;
Y represents O;
D represents OH;
E represents OH;
—O — J is selected from linear or branched C ₁ -C ₁₀ alkyl unsubstituted or substituted with phenyl C ₁ -C ₁₀ alkoxy, —O (CH ₂ ) _n OH, —O (C = O) R ¹ , —O (C = O) OR ¹ and -O (C = O) NR ¹ R ² ,
OL is selected from C ₁ -C ₁₀ alkoxy, -O (C = O) R ¹ , -O (C = O) OR ¹ and -O (C = O) NR ¹ R ² ,

denotes a double bond,
where R ¹ and R ² are as defined in paragraph 1 9. A method of obtaining a derivative of indanone according to claim 1, including:
reacting a compound of formula 1, where X is O, Y is O, and each D and E is OH, with thionyl chloride or oxalyl chloride in the presence of a base in a solvent, and then reacting with ammonia to give a compound of formula 2 (step 1); and
acylating or alkylating a compound of formula 2 in the presence of a base in a solvent to obtain a compound of formula 1b (step 2), as illustrated in the following reaction scheme 2:
[Reaction scheme 2]

Where
the compound of formula 1b is a derivative of formula 1 according to claim 1, its pharmaceutically acceptable salt or its optical isomer,
A ¹ , A ² , A ³ , A ⁴ , G ¹ , G ² , G ³ , G ⁴ , and Z are as defined in formula 1 of claim 1, and
X represents O,
Y represents O;
—O — J is selected from linear or branched C ₁ -C ₁₀ alkyl unsubstituted or substituted with phenyl C ₁ -C ₁₀ alkoxy, —O (CH ₂ ) _n OH, —O (C = O) R ¹ , —O (C = O) OR ¹ , -O (C = O) NR ¹ R ² ,
—NH — L is selected from the group consisting of —NR ¹ R ² , —NR ¹ (C = O) R ² , —NR ¹ (C = O) OR ² , —NR ¹ (C = O) —NR ¹ R ² , -NR ¹ (C = O) NR ² OR ³ , -NR ¹ (SO ₂ ) R ² , -NR ¹ (C = S) -NR ¹ R ² , -NR ¹ (P = O) (OR ² ) ₂ or

denotes a double bond; and
R ¹ , R ² , R ³ and R ⁴ are as defined in paragraph 1. 10. A pharmaceutical composition for the prophylaxis or treatment of a viral disease, comprising, as an active ingredient, an indanone derivative represented by chemical formula 1 according to claim 1, a pharmaceutically acceptable salt thereof or an optical isomer thereof. 11. The pharmaceutical composition of claim 10, wherein the viral disease is a disease caused by the coxsackie virus. 12. The pharmaceutical composition according to p. 10, where the viral disease is a disease caused by poliomyelitis virus. 13. The pharmaceutical composition according to p. 10, where the viral disease is a disease caused by echovirus. 14. The pharmaceutical composition according to claim 10, where the viral disease is a disease caused by enterovirus. 15. The pharmaceutical composition according to p. 10, where the viral disease is a disease caused by rhinovirus. 16. The pharmaceutical composition of claim 10, wherein the viral disease is a disease caused by picornavirus. 17. The pharmaceutical composition of claim 10, wherein the viral disease is poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, viral pemphigus of the mouth and limbs, pemphigus, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis flu, vesicular pharyngitis, foot and mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.