GB841524A - Improvements in or relating to indole derivatives - Google Patents
Improvements in or relating to indole derivativesInfo
- Publication number
- GB841524A GB841524A GB3314055A GB3314055A GB841524A GB 841524 A GB841524 A GB 841524A GB 3314055 A GB3314055 A GB 3314055A GB 3314055 A GB3314055 A GB 3314055A GB 841524 A GB841524 A GB 841524A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indole
- phthalimidoethyl
- benzyloxy
- ethyl
- sulphate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises indoles of the formula as below, substituted in the benzene ring by one or more alkoxy, aryloxy or aralkoxy groups <FORM:0841524/IV(b)/1> where A is a saturated hydrocarbon residue of not more than 6 carbon atoms and R1 is an amino group mono-acylated with an aliphatic, aromatic or heterocyclic mono- or di-carboxylic acid. The compounds are made by hydrolysis of the esters, and if in the starting material R1 is phthalimido this is converted into phthaloylamino at the same time, e.g. by using alcoholic potash for the hydrolysis. The products can be decarboxylated and hydrolysed to give 3-aminoalkyl-indoles, in which the substituent in the benzene ring can be converted into hydroxyl. In examples: (1) ethyl 5-benzyloxy-3 - (b - phthalimidoethyl) - indole - 2 - carboxylate is hydrolysed to 5-benzyloxy-3-b -(o-carboxybenzamido) - ethyl - indole - 2 - carboxylic acid, which on heating gives 5-benzyloxy-3 - (b - phthalimidoethyl) - indole; treatment of this with hydrazine yields 5-benzyloxytryptamine (isolated as sulphate), which is hydrogenolysed to serotonine (isolated as the creatinine sulphate); (2) ethyl-4 : 5 : 6-trimethoxy - 3 - (b - phthalimidoethyl) - indole - 2-carboxylate is hydrolysed to 4 : 5 : 6 - trimethoxy - 3 - b - (o - carboxybenzamido) - ethylindole-2-carboxylic acid, heated to give 4 : 5 : 6-trimethoxy - 3 - (b - phthalimidoethyl) - indole and converted to 4 : 5 : 6-trimethoxytryptamine (isolated as sulphate); (3) preparation as in (2) of 5-methoxy-3-b -(o-carboxybenzamido) - ethyl - indole - 2 - carboxylic acid, 5-methoxy - 3 - (b - phthalimidoethyl) - indole and 5 - methoxy - tryptamine (isolated as sulphate); (4) preparation as in (1) of 6-benzyloxy - 3 - b - (o - carboxybenzamido)-ethyl - indole - 2 - carboxylic acid, 6 - benzyloxy - 3 - (b - phthalimidoethyl) - indole, 6 - benzyloxytryptamine (sulphate) and 6-hydroxytryptamine (creatinine sulphate). The ester starting materials are made from the appropriate substituted aniline diazotized and reacted with an a -alkyl-acetoacetic ester. Examples show the preparation of the ethyl 3 - (b - phthalimidoethyl) - indole - 2 - carboxylates substituted in the benzene ring by 5-methoxy, 4 : 5 : 6-trimethoxy, 5-benzyloxy and 6-benzyloxy.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3314055A GB841524A (en) | 1955-11-18 | 1955-11-18 | Improvements in or relating to indole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3314055A GB841524A (en) | 1955-11-18 | 1955-11-18 | Improvements in or relating to indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB841524A true GB841524A (en) | 1960-07-20 |
Family
ID=10349060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3314055A Expired GB841524A (en) | 1955-11-18 | 1955-11-18 | Improvements in or relating to indole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB841524A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980368A (en) * | 1985-12-23 | 1990-12-25 | Beecham-Wuelfing Gmbh & Co. Kg | Tryptamine compounds, and methods of cerebrovascular treatment therewith |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| CN111960985A (en) * | 2018-08-08 | 2020-11-20 | 中国人民解放军总医院 | antitumor compounds |
-
1955
- 1955-11-18 GB GB3314055A patent/GB841524A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980368A (en) * | 1985-12-23 | 1990-12-25 | Beecham-Wuelfing Gmbh & Co. Kg | Tryptamine compounds, and methods of cerebrovascular treatment therewith |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| CN111960985A (en) * | 2018-08-08 | 2020-11-20 | 中国人民解放军总医院 | antitumor compounds |
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