CN110615777A - Compound and preparation method and application thereof - Google Patents

Abstract

The invention provides a compound and a preparation method and application thereof, the compound with the structure of formula (I) provided by the invention selects a specific structure, and experiments show that the compound can be detected in real time by a fluorescence technology and has the advantages of high detection sensitivity, quick detection, good biocompatibility and the like; and the antibacterial compound can realize controllable, broad-spectrum and efficient sterilization function while quickly diagnosing bacterial infection, is an antibacterial compound integrating diagnosis and treatment functions, and has wide application prospect in the anti-infection medical field.

Description

Compounds and their preparation methods and applications

technical field

The invention relates to the technical field of medicine, in particular to a compound and its preparation method and application.

Background technique

Bacterial infections are responsible for approximately one-third of global deaths and pose a serious threat to public health worldwide. In recent years, problems such as bacterial resistance caused by the irrational use and abuse of antibiotics have further aggravated the situation of global bacterial infections. Early rapid diagnosis of bacterial infection facilitates timely acquisition of bacterial infection status and timely adoption of effective treatment measures, which can greatly reduce the difficulty of treatment of infectious diseases, shorten treatment time, and improve treatment effects. So far, although a variety of mature technologies (such as standard plate counting and polymerase chain reaction) have been used for precise bacterial detection, these methods are usually time-consuming, cumbersome and highly dependent on sophisticated equipment and professional technicians. This greatly limits their application in rapid detection. In contrast, fluorescent techniques offer an attractive option for rapid and reliable bacterial detection due to their real-time detection, high sensitivity, non-invasiveness, and affordability.

At present, the process of bacterial diagnosis and treatment is independent in clinical application, and the interval from diagnosis to treatment process is long, which inevitably delays the best treatment time, reduces the treatment effect and increases the economic and psychological burden of patients . Therefore, "personalized" treatment strategies that effectively combine diagnosis and treatment have become a research hotspot in recent years. However, some antibacterial systems for diagnosis and treatment that have been developed so far are mostly functional integration of multiple materials, the preparation process is cumbersome, the process is difficult, and some systems are not broad-spectrum bactericidal or prone to bacterial drug resistance. Therefore, how to realize the simple and effective integration of diagnosis and inactivation of bacteria, especially drug-resistant bacteria, is a research hotspot and difficulty in the current anti-bacterial infection research.

Contents of the invention

In view of this, the technical problem to be solved by the present invention is to provide a compound and its preparation method and application. The compound provided by the present invention can realize the detection of broad-spectrum bacteria while realizing rapid and non-invasive bacterial detection of broad-spectrum bacteria. Efficient inactivation.

The present invention provides a kind of compound, has the structure shown in formula (I):

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

_{R1 is} selected from Wherein, R ₄ is selected from C ₁ -C ₁₈ alkyl or C6-C50 aryl, R ₅ and R ₆ are independently selected from -H and C ₁ -C ₁₈ alkyl;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C20 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C20 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br.

Preferably, the R ₂ is selected from -H, C3-C12 alkyl, C6-C30 aryl, -OH, C3-C12 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br.

Preferably, the R ₃ is selected from -H, C3-C12 alkyl, C6-C30 aryl, -OH, C3-C12 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br.

Preferably, the R ₄ is selected from -H, a C3-C12 alkyl group or a C6-C30 aryl group.

Preferably, the R ₅ and R ₆ are independently selected from -H or a C3-C12 alkyl group.

The present invention provides a kind of preparation method of the compound described in the present invention, comprising:

1) the compound of formula (II) structure and the compound of formula (III) structure are mixed reaction, obtain the compound of formula (IV) structure,

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

2) converting the compound of formula (IV) into a compound of formula (I);

Wherein, R ₁ is selected from Wherein, R ₄ is selected from a C ₁ -C ₁₈ alkyl group or a C6-C50 aryl group, and R ₅ and R ₆ are independently selected from -H and a C ₁ -C ₁₈ alkyl group.

The present invention provides an application of the compound with the structure of formula (I) described in the present invention in the preparation of a medicine or device integrating bacterial diagnosis and treatment.

The present invention also provides a medicine integrating bacterial diagnosis and treatment, comprising: the compound of formula (I) described in the present invention and pharmaceutically acceptable auxiliary materials;

Wherein, the auxiliary material is one or more of solvents, auxiliary agents and carriers.

The present invention also provides a photosensitive antibacterial drug, which has the structure shown in formula (IV),

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -C1 or -Br.

Preferably, the photosensitive wavelength of the photosensitive antibacterial drug is 300-1100 nm.

Compared with the prior art, the present invention provides a compound and its preparation method and application. The compound provided by the present invention has the structure of formula (I) by selecting a specific structure and finding through experiments that the compound provided by the present invention can pass Fluorescence technology detects bacteria in real time, and has the advantages of high detection sensitivity, rapid detection, and good biocompatibility; and while rapidly diagnosing bacterial infections, it can also achieve controllable, broad-spectrum, and efficient bactericidal functions. The antibacterial compound with functions integrated has broad application prospects in the field of anti-infection medicine.

Description of drawings

Figure 1 is a schematic diagram of the structure and synthesis of CORM and CORM-Ac;

Fig. 2 is the ¹ HNMR spectrogram of CORM;

Fig. 3 is the ESI-MS spectrogram of CORM;

Fig. 4 is the ¹ HNMR spectrogram of CORM-Ac;

Fig. 5 is the ESI-MS spectrogram of CORM-Ac;

Figure 6 shows the CO release from CORM;

Figure 7 is a diagram of the fluorescent color change of the molecular solution before and after the invasion of Gram-positive bacteria (Staphylococcus aureus), negative bacteria (Escherichia coli), and drug-resistant bacteria (Methicillin-resistant Staphylococcus aureus);

Fig. 8 does not add antibacterial flavonoid molecules in the dark, Gram-positive bacteria, negative bacteria, and drug-resistant bacteria solution coating plate diagram;

Fig. 9 adds antibacterial flavonoid molecules in the dark, Gram-positive bacteria, negative bacteria, and drug-resistant bacteria solution coating plate diagram;

Fig. 10 is that light does not add antibacterial flavonoid molecules, Gram-positive bacteria, negative bacteria, and drug-resistant bacteria solution coating plate diagram;

Fig. 11 is a diagram of a flat plate coated with a solution of light plus antibacterial flavonoids, Gram-positive bacteria, negative bacteria, and drug-resistant bacteria.

Detailed ways

The present invention provides a kind of compound, has the structure shown in formula (I):

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

_{R1 is} selected from Wherein, R ₄ is selected from C ₁ -C ₁₈ alkyl or C6-C50 aryl, R ₅ and R ₆ are independently selected from -H and C ₁ -C ₁₈ alkyl;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br.

According to the present invention, the R ₂ is preferably -H, C3-C12 alkyl, C6-C30 aryl, -OH, C3-C12 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N(CH ₂ CH ₃ ) ₂ , -F, -Cl or -Br, more preferably -H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, -OH, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, isopentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n- Decyloxy, -COOH, _-NH2 , -N( _CH3 ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl, or -Br.

According to the present invention, the R3 is preferably -H, C3-C12 alkyl, C6-C30 aryl, -OH, C3-C12 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) _2. -N(CH ₂ CH ₃ ) ₂ , -F, -Cl or -Br, more preferably -H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert Butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, -OH, methoxy, ethoxy, n- Propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-decyl Oxy, -COOH, _-NH2 , -N( _CH3 ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl, or -Br.

According to the present invention, the R4 is preferably -H, C3 _- C12 alkyl or C6-C30 aryl, more preferably -H, methyl, ethyl, n-propyl, isopropyl, n-butyl , isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, phenyl, naphthyl, anthracenyl or phenanthrenyl.

According to the present invention, the R5 is preferably -H or C3-C12 alkyl, more preferably -H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl , n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl or n-decyl.

According to the present invention, the R6 is preferably -H or C3 _- C12 alkyl, more preferably -H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl , n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl or n-decyl.

More specifically, the compound is as follows:

The present invention also provides a preparation method of the compound described in the present invention, comprising:

The compound of formula (II) structure and the compound of formula (III) structure are mixed reaction, obtain the compound of formula (IV) structure,

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

The compound of formula (IV) structure is converted into the compound of formula (I) structure;

Wherein, R ₁ is selected from Wherein, R ₄ is selected from a C ₁ -C ₁₈ alkyl group or a C6-C50 aryl group, and R ₅ and R ₆ are independently selected from -H and a C ₁ -C ₁₈ alkyl group.

According to the present invention, the compound of the formula (II) and the compound of the formula (III) are mixed and reacted to obtain the compound of the formula (IV), wherein, the present invention has no special requirements on the reaction conditions and the amount of each raw material , those skilled in the art can select a suitable preparation process according to the existing preparation methods of similar compounds.

According to the present invention, the present invention converts the compound of formula (IV) structure into the compound of formula (I) structure; Wherein, the present invention has no special requirements to the reaction conditions and the consumption of each raw material, those skilled in the art can according to existing The preparation method of similar compounds selects the appropriate preparation process.

The present invention also provides an application of the compound of the formula (I) described in the present invention in the preparation of a medicine or device integrating bacterial diagnosis and treatment.

The present invention also provides a medicine integrating bacterial diagnosis and treatment, comprising: the compound of formula (I) described in the present invention and pharmaceutically acceptable auxiliary materials;

Wherein, the auxiliary material is one or more of solvents, auxiliary agents and carriers, more specifically, the solvent is preferably water, methanol, ethanol, acetonitrile, acetic acid, acetone, chloroform, DMSO, DMF and THF One or more; the carrier is one or more of polyethylene, polypropylene, polystyrene, polyvinyl alcohol, polycarbonate and polyurethane; the shape of the carrier is flat film, non-woven fabric, Hydrogel, rubber or elastomer; wherein, when the drug is a compound of the formula (I) structure and a solvent, in the drug, the drug concentration of the compound of the formula (I) structure is 1-1000 μg/mL; when When the drug is a carrier drug, the compound of the formula (I) is loaded on the carrier by methods such as dip coating, spray coating, blending, adsorption and grafting.

The present invention also provides a photosensitive antibacterial drug, which has the structure shown in formula (IV),

Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-;

R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br;

R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br.

Wherein, the photosensitive wavelength of the photosensitive antibacterial drug is 300-1100nm, more preferably 300-900nm; the light power is 0.01W-100W, and the irradiation time is 0-24h.

The compound of the formula (I) structure provided by the present invention is found through experiments that the compound of the formula (I) structure can undergo a rapid change in fluorescence color in the presence of bacteria, which can then be used to indicate bacterial infection, and can be determined according to the change in fluorescence intensity The concentration of infected bacteria; and then through the light irradiation drug delivery system, it was found that it can produce carbon monoxide (CO) gas with broad-spectrum bactericidal properties, which can kill Gram-positive bacteria, Gram-negative bacteria and drug-resistant bacteria; and then Realize the diagnosis and treatment of bacteria in one.

A clear and complete description will be made below in conjunction with the technical solutions of the embodiments of the present invention. Apparently, the described embodiments are only some of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

Example 1

The preparation method of the integrated antibacterial formula (I-1) (CORM-Ac) for diagnosis and treatment, the reaction process is as shown in Figure 1, and Figure 1 is a schematic diagram of the structure and synthesis of CORM and CORM-Ac; the specific synthesis process is as follows:

Synthesis of 3-hydroxy-2-phenyl-4H-benzo[h]chromen-4-one 3-hydroxy-2-phenyl-4H-benzo[h]chromen-4-one (CORM, Figure 1A) : Add benzaldehyde (5mmol), 1'-hydroxy-2'-acetylacetone (5mmol) and potassium hydroxide (25%, 15ml) into ethanol (40ml), stir at room temperature for 15h. Hydrogen peroxide (5ml, 30%) was then added and the mixture was stirred for a further 12h at room temperature. After the reaction, the mixture was poured into ice water and acidified with dilute hydrochloric acid. The resulting yellow-brown precipitate was filtered and washed with water, and the crude product was recrystallized from ethanol with a yield of about 52%.

The structure of the product obtained is identified, and the results are shown in Fig. 2～Fig. 3, and Fig. 2 is the ¹ HNMR spectrogram of CORM; Fig. 3 is the ESI-MS spectrogram of CORM; As can be seen from the figure: ¹ H NMR (DMSO -d6, 300MHz,) δ9.88(S, 1H), 8.68(dd, J=6.1, 3.3Hz, 1H), 8.35(d, J=7.5Hz, 2H), 8.14(dd, J=6.1, 3.1 Hz, 1H), 8.07(d, J=8.7Hz, 1H), 7.93(d, J=8.8Hz, 1H), 7.84(dd, J=6.2, 3.2Hz, 2H), 8.68(dd, J=6.1 , 3.1, 3Hz, J=6.1, 3.3Hz, 1H), 8.68 (d, J=6.1, 3.1, J=6.1, 3.1Hz, 3 1h). Product ESI-MS: _{C19H13O3 [} MH]+: _289.3 .

Synthesis of 4-oxo-2-phenyl-4H-benzo[h]chromen-3-y1 acetate4-oxo-2-phenyl-4H-benzo[h]chromen-3-yl acetate (CORM -Ac):

CORM (5 mmol) and acetic anhydride (25 mmol) were dissolved in THF (40 mL), then 4-dimethylaminopyridine (DMAP, 0.08 mmol) was added as a catalyst. After stirring at room temperature for 18 hours, the resulting mixture was poured into water, and a white precipitate was obtained by filtration (about 60%) as a compound having the structure of formula (I-1).

Structural identification of the obtained compound is carried out, and the results are shown in Figures 4 to 5, Figure 4 is the ¹ HNMR spectrum of CORM-Ac; Figure 5 is the ESI-MS spectrum of CORM-Ac; as can be seen from the figure, ¹ H NMR (DMSO-d6, 300MHz): δ8.63 (d, j = 8.7Hz, 1h), 8.18 (d, = 7.5Hz, 1h), 8.08-8.02 (m, 4h), 7.89-7.82 (m, 2h), 7.68(m, 3h), 2.38(s, 3h). Product ESI-MS: _C21H15O4 [MH] ₊ : _331.4 .

The CO release of the obtained compound CORM was detected: measured using a commercial CO detector. The specific steps are: dissolving CORM in acetonitrile to prepare a 1 mg/mL solution. Take 1mL of this solution and place it in a 20mL Agilent vial and seal it with oxygen. Then use the simulated fluorescent lamp (37500lx) to continuously irradiate the vial for 12 hours, and then use a commercial CO detector to detect CO. The detection results are shown in Figure 6. Figure 6 shows the CO release of CORM, where (a) CORM was illuminated for 12 hours, (b) CORM was not exposed to light, and (c) acetonitrile solution was illuminated for 12 hours.

Example 2

Select Staphylococcus aureus as a representative Gram-positive bacterium, add 30 μg/mL compound solution of formula (I-1) (CORM-Ac/DMSO solution) into 10 ⁶ cells/mL Staphylococcus aureus suspension, shake After incubating for 30 min, under the irradiation of a portable ultraviolet lamp (365nm), a fluorescent image of the suspension was taken by a digital camera, and the results are shown in FIG. 7 .

Example 3

Select Escherichia coli as a representative Gram-negative bacterium, add 30 μg/mL compound solution of formula (I-1) (CORM-Ac solution/DMSO) into 10 ⁶ cells/mL Escherichia coli suspension, shake and incubate for 30 minutes, Under the irradiation of a portable ultraviolet lamp (365nm), the fluorescent image of the suspension was taken by a digital camera, and the results are shown in Figure 7.

Example 4

Select methicillin-resistant Staphylococcus aureus as the representative drug-resistant bacteria, take 30 μg/mL compound solution of formula (I-1) (CORM-Ac/DMSO solution) and add 10 ⁶ cells/mL methicillin-resistant Staphylococcus aureus In the coccus suspension, after shaking and incubating for 30 min, under the irradiation of a portable ultraviolet lamp (365nm), the fluorescent image of the suspension was taken by a digital camera, and the results are shown in Figure 7.

Comparative example 1

Add an equal amount of DMSO solvent without the compound of formula (I-1) (CORM-Ac) into 10 ⁶ cells/mL Staphylococcus aureus suspension, shake and incubate for 30 minutes, store in dark place for 30 minutes, and put a certain amount of bacterial suspension Spread on LB agar plates and incubate at 37°C, and evaluate the bacterial activity by counting the number of viable bacterial colonies, the results are shown in Figure 8.

Comparative example 2

Add an equal amount of DMSO solvent that does not contain the compound of formula (I-1) (CORM-Ac) into 10 ⁶ cells/mL Escherichia coli suspension, shake and incubate for 30 minutes, store in the dark for 30 minutes, and spread a certain amount of bacterial suspension On LB agar plates and incubated at 37 °C, the bacterial activity was evaluated by counting the number of viable bacterial colonies, and the results are shown in Figure 8.

Comparative example 3

Add an equal amount of DMSO solvent not containing the compound of formula (I-1) (CORM-Ac) to 10 ⁶ cells/mL methicillin-resistant Staphylococcus aureus suspension, shake and incubate for 30 minutes, store in dark place for 30 minutes, and certain The amount of bacterial suspension was spread on LB agar plate and incubated at 37°C, and the bacterial activity was evaluated by counting the number of viable bacterial colonies, the results are shown in Figure 8.

Comparative example 4

Formula (I-1) compound (CORM-Ac) in 10 ⁶ cells/mL Staphylococcus aureus suspension, shake and incubate for 30min after fluorescence transition, store in dark place for 30min, spread a certain amount of bacterial suspension on LB agar plate and incubated at 37°C, the bacterial activity was evaluated by counting the number of viable bacterial colonies, and the results are shown in Figure 9.

Comparative Example 5

Formula (I-1) compound (CORM-Ac) in 10 ⁶ cells/mL Escherichia coli suspension, shaking and incubating for 30 minutes after the fluorescence transition, stored in the dark for 30 minutes, spread a certain amount of bacterial suspension on the LB agar plate, And incubated at 37°C, the bacterial activity was evaluated by counting the number of live bacterial colonies, the results are shown in Figure 9.

Comparative example 6

Formula (I-1) compound (CORM-Ac) in 10 ⁶ cells/mL methicillin-resistant Staphylococcus aureus suspension, shake and incubate for 30 minutes, after fluorescence transition, store in dark place for 30 minutes, and apply a certain amount of bacterial suspension On LB agar plates and incubated at 37 °C, the bacterial activity was evaluated by counting the number of viable bacterial colonies, and the results are shown in Figure 9.

Comparative Example 7

Add an equal amount of DMSO solvent without the compound of formula (I-1) (CORM-Ac) into 10 ⁶ cells/mL Staphylococcus aureus suspension, shake and incubate for 30 minutes, and then irradiate the suspension with a simulated sun lamp for 30 minutes. The amount of bacterial suspension was spread on LB agar plate and incubated at 37°C, and the bacterial activity was evaluated by counting the number of viable bacterial colonies, the results are shown in Figure 10.

Comparative Example 8

Add an equal amount of DMSO solvent without the compound of formula (I-1) (CORM-Ac) into 10 ⁶ cells/mL Escherichia coli suspension, shake and incubate for 30 minutes, then irradiate the suspension with a simulated sun lamp for 30 minutes, and a certain amount of bacteria The suspension was spread on LB agar plates and incubated at 37°C, and the bacterial activity was evaluated by counting the number of viable bacterial colonies, the results are shown in Figure 10.

Comparative Example 9

Add an equal amount of DMSO solvent that does not contain the compound of formula (I-1) (CORM-Ac) to 10 ⁶ cells/mL methicillin-resistant Staphylococcus aureus suspension, shake and incubate for 30 minutes, and then irradiate the suspension with a simulated sun lamp For 30 minutes, a certain amount of bacterial suspension was spread on the LB agar plate, and incubated at 37°C, and the bacterial activity was evaluated by counting the number of viable bacterial colonies. The results are shown in Figure 10.

Example 5

Formula (I-1) compound solution (CORM-Ac/DMSO solution) in 10 ⁶ cells/mL Staphylococcus aureus suspension, shake and incubate for 30min after fluorescence transition, use simulated sun lamp to irradiate the suspension for 30min, and a certain amount of bacteria The suspension was spread on LB agar plates and incubated at 37°C, and the bactericidal activity was evaluated by counting the number of viable bacterial colonies, the results are shown in Figure 11.

Example 6

Formula (I-1) compound solution (CORM-Ac/DMSO solution) in 10 ⁶ cells/mL Escherichia coli suspension, shaking and incubating for 30 minutes after the fluorescence transition, irradiated the suspension with simulated sun lamp for 30 minutes, and a certain amount of bacterial suspension Spread on LB agar plates and incubate at 37°C, and evaluate the bactericidal activity by counting the number of viable bacterial colonies, the results are shown in Figure 11.

Example 7

Formula (I-1) compound solution (CORM-Ac/DMSO solution) in 10 ⁶ cells/mL methicillin-resistant Staphylococcus aureus suspension, shaking and incubating for 30 minutes, after fluorescence transition, irradiate the suspension with simulated sun lamp for 30 minutes, A certain amount of bacterial suspension was spread on LB agar plate and incubated at 37°C, and the bactericidal activity was evaluated by counting the number of viable bacterial colonies, the results are shown in Figure 11.

Summary: From the records of the examples and comparative examples, it can be concluded that the compound of formula (I) can change color rapidly during bacterial infection, so that the detection of bacterial infection can be realized; then the detection system is illuminated, and it is found that the The system exhibits good antibacterial effect, that is, the compound provided by the invention can realize the diagnosis and treatment of broad-spectrum bacteria at the same time.

The descriptions of the above embodiments are only used to help understand the method and core idea of the present invention. It should be pointed out that for those skilled in the art, without departing from the principles of the present invention, some improvements and modifications can be made to the present invention, and these improvements and modifications also fall within the protection scope of the claims of the present invention.

Claims (10)

1. A compound having a structure shown in formula (I): Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-; _{R1 is} selected from Wherein, R ₄ is selected from C ₁ -C ₁₈ alkyl or C6-C50 aryl, R ₅ and R ₆ are independently selected from -H and C ₁ -C ₁₈ alkyl; R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C20 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -C1 or -Br; R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C20 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br. 2. The compound according to claim ₁ , wherein said R is selected from the group consisting of -H, C3-C12 alkyl, C6-C30 aryl, -OH, C3-C12 alkoxy, - COOH, _-NH2 , -N( _CH3 ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br. 3. The compound according to claim 1, wherein said _R is selected from the group consisting of -H, C3～C12 alkyl, C6～C30 aryl, -OH, C3～C12 alkoxy, - COOH, _-NH2 , -N( _CH3 ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br. 4. The compound according to claim 1, wherein the R ₄ is selected from -H, C3-C12 alkyl or C6-C30 aryl. 5. The compound according to claim 1, characterized in that, said R ₅ and R ₆ are independently selected from -H or a C3-C12 alkyl group. 6. A preparation method of the compound according to claim 1, comprising: 1) The compound of formula (II) structure and the compound of formula (III) structure are mixed and reacted to obtain the compound of formula (IV) structure, Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-; R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -C1 or -Br; R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br; 2) converting the compound of formula (IV) into a compound of formula (I); Wherein, R ₁ is selected from Wherein, R ₄ is selected from a C ₁ -C ₁₈ alkyl group or a C6-C50 aryl group, and R ₅ and R ₆ are independently selected from -H and a C ₁ -C ₁₈ alkyl group. 7. Application of a compound of formula (I) according to any one of claims 1 to 5 in the preparation of a medicine or device integrating bacterial diagnosis and treatment. 8. A medicine integrating bacterial diagnosis and treatment, comprising: the compound of the formula (I) structure described in any one of claims 1 to 5 and pharmaceutically acceptable auxiliary materials; Wherein, the auxiliary material is one or more of solvents, auxiliary agents and carriers. 9. A photosensitive antibacterial drug having a structure shown in formula (IV), Wherein, X is selected from =O or =S, Y is selected from -O- or -NH-; R ₂ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -C1 or -Br; R ₃ is selected from -H, C1-C20 alkyl, C6-C50 aryl, -OH, C1-C15 alkoxy, -COOH, -NH ₂ , -N(CH ₃ ) ₂ , -N( _{CH2CH3 )2 ,} -F, -Cl or -Br. 10. The photosensitive antibacterial drug according to claim 9, characterized in that, the photosensitive wavelength of the photosensitive antibacterial drug is 300-1100nm.