β-Carboline-cyanoisoflavone compound and its preparation method and application

Abstract

The present invention relates to the field of biomedicine, and more specifically to a novel class of β-carboline-cyanoisoflavonoid compounds, their preparation methods, and applications. The β-carboline-cyanoisoflavonoid compounds have the structure shown in Formula I: #imgabs0#, where R is selected from one of H, NO2, NH2, N(Me)2, and N(Ph)2; and X is selected from one of NMe, O, S, and Se. The β-carboline-cyanoisoflavonoid compounds disclosed herein exhibit excellent photodynamic properties, along with good cytotoxicity and photodynamic therapeutic activity against tumor cells. These compounds are beneficial for selectively inhibiting tumor tissue and cell proliferation, and thus have important application implications for the treatment of solid tumors.

Description

Technical Field

[0001] The present invention relates to the field of biomedicine technology, and in particular to a novel β-carboline-cyanoisoflavone compound and a preparation method and application thereof. Background Art

[0002] Photodynamic therapy (PDT), an innovative treatment method, has attracted widespread attention and application in the medical field in recent years. PDT consists of two main components: a photosensitizer and light. Photosensitizers are specialized compounds that, when exposed to light of a specific wavelength, generate reactive oxygen species, which act as a photodynamic therapy.

[0003] Photodynamic therapy is divided into type I and type II. Type I photodynamic therapy does not rely on oxygen. It is the photosensitizer molecule that directly transfers energy to the target cells or tissues. This energy transfer can cause ·O 2- ,·OH and other reactive oxygen groups, thereby exerting a photodynamic therapeutic effect on the target cells or tissues. Type II photodynamic therapy requires the presence of oxygen. When the photosensitizer absorbs light of a specific wavelength, it transfers energy to nearby oxygen molecules. This energy transfer causes the production of highly reactive singlet oxygen. Singlet oxygen is a potent cytotoxic agent that can directly damage cell structures such as lipids, proteins and DNA, leading to cell death. Compared with traditional treatments (surgery, chemotherapy, immunotherapy, etc.), photodynamic therapy has the advantages of being highly effective, painless, non-invasive and having few side effects. It has broad application prospects in the fields of skin diseases, oral cavity, and especially in cancer treatment.

[0004] β-Carboline is a natural alkaloid often used as a drug backbone. It possesses a wide range of biological activities, including antimalarial, antiviral, and antifungal properties, and plays a particularly important role in cancer treatment. β-Carboline can inhibit tumor cell proliferation and growth through various pathways, including inducing apoptosis, blocking tumor angiogenesis, and inhibiting tumor cell invasion and metastasis. Summary of the Invention

[0005] To improve the efficacy of photodynamic therapy, the present invention considers that 2-(4H-methylene-4-ylidene)malononitrile is a strong electron-withdrawing group that can be introduced into photosensitizers to produce longer emission wavelengths. In view of this, the 2-(4H-methylene-4-ylidene)malononitrile group (electron acceptor) containing oxygen, sulfur, and selenium atoms is coupled with β-carboline (electron donor) to form a donor-π-acceptor (D-π-A) skeleton. A novel β-carboline-cyanoisoflavone compound, its preparation method, and its application are designed and synthesized, and are proposed for tumor treatment through the action of photodynamic therapy.

[0006] In order to achieve the above object, the technical solution adopted by the present invention is as follows:

[0007] A novel β-carboline-cyanoisoflavone compound having the structure shown in general formula I:

[0008]

[0009] Wherein, R is selected from one of H, NO2, NH2, N(Me)2, and N(Ph)2; X is selected from one of NMe, O, S, and Se.

[0010] The preferred structure is shown in Table 1:

[0011] Table 1. Codes of some compounds of formula I and their corresponding structures

[0012]

[0013] The compound codes of the above general formula I and their corresponding compound names are as follows:

[0014] I1: (E)-2-(2-(2-(1,9-dimethyl-9H-pyrrolo[3,4-b]indol-3-yl)vinyl)-4H-thiazol-4-ylidene)malononitrile;

[0015] I2: (E)-2-(2-(2-(1,9-dimethyl-9H-pyrido[3,4-b]indol-3-yl)vinyl)-4H-seleniumchrome-4-ylidene)malononitrile;

[0016] I3: (E)-2-(2-(2-(6-(diphenylamino)-1,9-dimethyl-9H-pyrido[3,4-b]indol-3-yl)vinyl)-4H-seleniumchromium-4-ylidene)malononitrile.

[0017] Another object of the present invention is to provide a method for preparing a novel β-carboline-cyanoisoflavone compound.

[0018] The steps include:

[0019] a) condensing 1,9-dimethyl-6R-9H-pyrido[3,4-b]indole-3-carboxaldehyde and compound 2 in the presence of a base to obtain a β-carboline-cyanoisoflavone compound I wherein R is H or NO2,

[0020] b) R is NO2 compound I is reduced to give R is NH2 β-carboline - cyanoisoflavone compound I,

[0021]

[0022] or,

[0023] a'). 1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde is brominated to obtain 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde,

[0024]

[0025] b'). 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde is reacted with diphenylamine or dimethylamine in the presence of a catalyst to obtain compound 4,

[0026]

[0027] c') condensing compound 4 and compound 2 in the presence of a base to obtain a β-carboline-cyanoisoflavone compound I wherein R is N(Me)2 or N(Ph)2,

[0028]

[0029] X is selected from one of NMe, O, S and Se.

[0030] A specific example of the method of the present invention includes the following steps:

[0031] a) dissolving 1,9-dimethyl-6R-9H-pyrido[3,4-b]indole-3-carboxaldehyde and compound 2 in anhydrous ethanol, adding piperidine as a base to carry out a condensation reaction to obtain a β-carboline-cyanoisoflavone compound I wherein R is H or NO2;

[0032] b) R is NO2 β-carboline - cyano isoflavone compound I using iron powder reduction to give R is NH2 β-carboline - cyano isoflavone compound I;

[0033] or,

[0034] a') dissolving 1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde in anhydrous THF, adding NBS, and reacting to obtain 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde;

[0035] b'). Reaction of 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde with diphenylamine or dimethylamine in the presence of palladium acetate, tri-tert-butylphosphine and cesium carbonate to obtain compound 4;

[0036] c') Compound 4 and Compound 2 are dissolved in anhydrous ethanol, and 2 drops of piperidine are added as a base to obtain β-carboline-cyanoisoflavone compound I wherein R is N(Me)2 or N(Ph)2.

[0037] Another object of the present invention is to provide a novel β-carboline-cyanoisoflavone compound for use in the preparation of a photosensitizer, wherein the photosensitizer generates reactive oxygen molecules (including superoxide anions and singlet oxygen) under 520 nm light excitation.

[0038] Another object of the present invention is to provide the use of a novel β-carboline-cyanoisoflavone compound in the preparation of a photodynamic therapy drug. The photodynamic therapy drug is an anti-tumor drug. The tumors include colon cancer, lung cancer, and breast cancer. The novel β-carboline-cyanoisoflavone compound exhibits selective cytotoxic activity in tumor cells, exerting a selective chemotherapeutic effect in tumor cells while exhibiting minimal toxicity to normal cells.

[0039] Beneficial effects of the present invention:

[0040] The present invention discloses novel β-carboline-cyanoisoflavone compounds. Unlike conventional β-carboline compounds, these compounds contain oxygen, sulfur, and selenium atoms, resulting in superior photodynamic properties. Upon illumination, these novel β-carboline-cyanoisoflavone compounds generate reactive oxygen species, including superoxide anions and singlet oxygen, capable of simultaneously exerting both Type I and Type II photodynamic effects. Furthermore, a comparison of cytotoxicity and photodynamic therapeutic activity demonstrates that these compounds selectively exert photodynamic effects at tumor sites, inhibiting tumor cell proliferation while exhibiting minimal toxic side effects on normal cells. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 It is the ultraviolet absorption spectrum of compound I1-I3 of the present invention, the horizontal axis is wavelength, and the vertical axis is absorbance value (ac corresponds to compound I1-I3 respectively).

[0042] Figure 2 It is the fluorescence emission spectrum of compound I1-I3 of the present invention, the abscissa is wavelength, and the ordinate is fluorescence intensity (ac corresponds to compound I1-I3 respectively).

[0043] Figure 3 1 is a fluorescence emission spectrum of active oxygen generated by compounds I1-I3 of the present invention, where the abscissa is wavelength and the ordinate is fluorescence intensity (ac corresponds to compounds I1-I3, respectively).

[0044] Figure 4 It is the fluorescence emission spectra of the superoxide anion generated by the compounds I1-I3 of the present invention, the abscissa is the wavelength, and the ordinate is the fluorescence intensity (ac corresponds to compounds I1-I3, respectively).

[0045] Figure 5It is the ultraviolet absorption spectrum of the singlet oxygen produced by the compounds I1-I3 of the present invention, the abscissa is the wavelength, and the ordinate is the absorbance value (ac corresponds to compounds I1-I3 respectively).

[0046] Figure 6 This is a comparison of the activity of the new β-carboline-cyanoisoflavone compound I2 in tumor cells and normal cells. DETAILED DESCRIPTION

[0047] The technical solutions in the embodiments of the present invention will be clearly and completely described below in conjunction with the accompanying drawings so that those skilled in the art can better understand the advantages and features of the present invention and thus more clearly define the scope of protection of the present invention. The embodiments described in the present invention are only a part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without making creative work are within the scope of protection of the present invention.

[0048]

[0049] Example 1: Preparation of (E)-2-(2-(2-(1,9-dimethyl-9H-pyrrolo[3,4-b]indol-3-yl)vinyl)-4H-thiazol-4-ylidene)malononitrile (I1)

[0050] Compound 1 (1 mmol) and compound 2 (1 mmol) were dissolved in anhydrous ethanol in a 25 mL Schlenk tube, and 2 drops of piperidine were added as a base. The mixture was reacted at 80°C for 30 min. After completion of the reaction, the solvent was dried and purified by column chromatography using dichloromethane:methanol (5:1, v / v) as the eluent to obtain the target compound I1 in a 65% yield.

[0051] (I1) Spectral data is: 1 H NMR(400MHz,DMSO-d6)δ8.73(m,1H,ArH),8.64(s,1H,ArH),8.38(m,1H,ArH),8.04(m,1H,ArH),7.94(m,1H,ArH),7.80–7.78(m,1H,ArH),7.76(d,J =1.3Hz,1H,ArH),7.71–7.68(m,2H,2ArH),7.67–7.64(m,1H,ArH),7.35(m,1H,CH=),7.30(d,J=1.2Hz,1H,CH=),4.19(s,3H,CH3),3.10(s,3H,CH3). 13C NMR(101MHz,DMSO-d6)δ156.0,151.6,143.0,142.8,142.6,137.8,136.3,132.9,132.3,129.2,128.0,127.1, 124.7,124.3,122.4,121.2,121.0,120.1,117.8,116.3,113.7,111.2,66.1,32.6,23.5.ESI-MS(m / z):calcd for C 27 H 18 N4S[M+H] + :431.1330,found 431.13180.

[0052] Example 2: Preparation of (E)-2-(2-(2-(1,9-dimethyl-9H-pyrido[3,4-b]indol-3-yl)vinyl)-4H-seleniumchromium-4-ylidene)malononitrile (I2)

[0053] Referring to the synthesis method of (I1) in Example 1, 2-(2-methyl-4H-selenium chromium-4-ylidene)malononitrile was used instead of 2-(2-methyl-4H-thiazole-4-ylidene)malononitrile to finally obtain compound I2 with a yield of 70%.

[0054] (I2) Spectral data is: 1 H NMR (400MHz, CDCl3) δ8.58(s,1H,ArH),8.18(d,J=7.9Hz,1H,ArH),8.11(d,J=7.9Hz,1H,ArH),7.95(s,1H,CH=),7.74(m ,2H,2ArH),7.64(m,2H,2ArH),7.52(d,J=4.3Hz,2H,2ArH),7.41–7.31(m,2H,2CH=),4.14(s,3H,CH3),3.17(s,3H,CH3). 13 C NMR(101MHz,DMSO-d6)δ193.3,155.6,153.3,144.5,143.3,143.1,139.2,136.9,130.2,129.8,129.7,129.2, 128.6,125.3,122.6,121.9,121.7,121.5,121.4,118.2,114.1,111.5,62.1,33.4,21.2.ESI-MS(m / z):calcd for C 27 H 18 N4Se[M+H] +:479.0775,found 479.07602.

[0055] Example 3: Preparation of (E)-2-(2-(2-(6-(diphenylamino)-1,9-dimethyl-9H-pyrido[3,4-b]indol-3-yl)vinyl)-4H-seleniumchromium-4-ylidene)malononitrile (I3)

[0056] Preparation of 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde (3)

[0057] 1,9-Dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde (1) (1 mmol) was dissolved in anhydrous THF, and 1.1 times the amount of NBS was added. The reaction was carried out at 65°C for 1 hour. After the reaction was completed, the solid was extracted and dried to obtain compound 3 with a yield of 75%.

[0058] Preparation of 6-(diphenylamino)-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde (4)

[0059] 6-Bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde (3) (1 mmol), palladium acetate (0.01 mmol), tri-tert-butylphosphine (0.01 mmol), cesium carbonate (2 mmol), and diphenylamine (4 mmol) were added to a 25 mL Schlenk tube with toluene as the solvent and reacted at 110°C for 12 h. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by column chromatography using ethyl acetate:petroleum ether (1:5, v / v) as the eluent to obtain compound 4 in a 75% yield.

[0060] Compound 2 (1 mmol) and compound 4 (1 mmol) were dissolved in anhydrous ethanol in a 25 mL Schlenk tube, and 2 drops of piperidine were added as a base. The mixture was reacted at 80°C for 30 min. After completion of the reaction, the solvent was evaporated and purified by column chromatography using dichloromethane:methanol (5:1, v / v) as the eluent to obtain the target compound I3 in a 70% yield.

[0061] (I3) Spectral data is: 1H NMR(400MHz,CDCl3)δ8.69(m,1H,ArH),8.13–8.10(m,1H,ArH),7.94(s,1H,ArH),7.87(t,J =2.5Hz,1H,ArH),7.81(s,1H,ArH),7.73(q,J=5.7Hz,3H,3ArH),7.65–7.59(m,1H,ArH),7. 55–7.50(m,2H,2ArH),7.47–7.43(m,1H,ArH),7.40(d,J=9.0Hz,1H,ArH),7.24(d,J=1.9Hz ,2H,2ArH),7.10(m,4H,4ArH),7.04–6.98(m,2H,2CH=),4.15(s,3H,CH3),3.11(s,3H,CH3). 13 C NMR(101MHz,DMSO-d6)δ193.3,168.6,160.1,148.4,144.3,143.3,143.1,141.0,137.3,137.0,134.9,132.9,132.4,131.6,131.5,131.5,130 .5,129.8,129.8,129.6,128.6,126.8,122.8,122.5,122.4,121.9,121.4,121.4,113.9,113.7,111.4,55.7,33.5,25.3.ESI-MS(m / z):calcd for C 39 H 27 N5Se[M+H] + :646.1510,found 646.14923.

[0062] Example 4: Ultraviolet absorption spectrum test of the novel β-carboline-cyanoisoflavone compound of the present invention

[0063] The compound of the present invention was dissolved in deionized water to prepare a 20 μM test solution, and its ultraviolet absorption spectrum data was measured using an ultraviolet-visible spectrophotometer.

[0064] The novel β-carboline-cyanoisoflavone compounds I1, I2 and I3 were used as representative compounds. The results showed that the UV maximum absorption wavelengths of the compounds I1, I2 and I3 of the present invention were in the range of 450-500 nm ( Figure 1 ).

[0065] Example 5: Fluorescence emission spectrum test of the novel β-carboline-cyanoisoflavone compound of the present invention

[0066] The compound of the present invention was dissolved in deionized water to prepare a 20 μM test solution, and its fluorescence emission spectrum data was measured using a fluorescence spectrometer.

[0067] The new β-carboline-cyanoisoflavone compounds I1, I2 and I3 were used as representative compounds. The results showed that the maximum fluorescence emission wavelength of the compounds I1, I2 and I3 of the present invention was around 700 nm ( Figure 2 ).

[0068] Example 6: Test of the ability of the novel β-carboline-cyanoisoflavone compound of the present invention to generate active oxygen species

[0069] Fluorescence spectroscopy was used to detect the ability of the compounds of the present invention to generate active oxygen species, using 2,7-dichlorodihydrofluorescein (DCFH) as an active oxygen scavenger. The specific method was to mix solutions of the compounds I1, I2, and I3 (20 μM) of the present invention with the scavenger DCFH, and then irradiate with laser for a certain period of time. The compounds of the present invention were detected at 520 nm (100 mW / cm 2 ) After laser irradiation, the changes in DCFH fluorescence intensity were detected.

[0070] The new β-carboline-cyanoisoflavone compounds I1, I2 and I3 were used as representative compounds. The results showed that ( Figure 3 ), the fluorescence intensity of the mixed solution of compounds I1, I2 and I3 and the capture agent DCFH at around 525 nm increased with the increase of illumination time, indicating that the compounds of the present invention can effectively generate reactive oxygen species after illumination and have the potential for photodynamic therapy.

[0071] Example 7: Test of the ability of the novel β-carboline-cyanoisoflavone compound of the present invention to generate superoxide anions

[0072] Fluorescence spectroscopy was used to detect the ability of the compounds of the present invention to generate superoxide anions. Dihydroethidium (DHE) was used as a superoxide anion scavenger. Specifically, solutions of the compounds I1, I2, and I3 (20 μM) of the present invention and the scavenger DHE were mixed, and then irradiated with laser for a certain period of time. The compounds of the present invention were detected at 520 nm (100 mW / cm 2 ) After laser irradiation, the changes in DHE fluorescence intensity were detected.

[0073] The new β-carboline-cyanoisoflavone compounds I1, I2 and I3 were used as representative compounds. The results showed that ( Figure 4 ), the maximum fluorescence intensity of the mixed solution of compounds I1, I2 and I3 and the capture agent DHE increased with the increase of illumination time, among which the increase of compound I2 was more obvious, indicating that the compounds of the present invention can effectively generate superoxide anions after illumination and can play the role of type I photodynamic therapy.

[0074] Example 8: Testing the Singlet Oxygen Generation Capacity of the Novel β-Carboline-Cyanoisoflavone Compounds of the Present Invention

[0075] The ability of the present compounds to generate singlet oxygen was tested by ultraviolet spectroscopy, with 1,3-diphenylbenzofuran (DPBF) as a singlet oxygen scavenger. Specifically, the present compounds I1, I2, and I3 (20 μM) were mixed with a solution of the scavenger DPBF, and then irradiated with laser for a certain period of time. The present compounds were detected at 520 nm (100 mW / cm 2 ) After laser irradiation, the changes in DPBF absorbance were detected.

[0076] The new β-carboline-cyanoisoflavone compounds I1, I2 and I3 were used as representative compounds. The results showed that ( Figure 5 ), the absorbance of the mixed solution of compounds I1, I2 and I3 and the scavenger DPBF at around 415 nm decreased with the increase of illumination time, and the maximum ultraviolet absorption values ​​of compounds I1 and I2 decreased significantly. At the same time, compounds I1 and I2 had high singlet oxygen quantum yields of 0.81 and 0.91, respectively, which clearly demonstrated that the compounds of the present invention can effectively generate singlet oxygen after illumination and can play a role in type II photodynamic therapy.

[0077] Example 9: Activity test of the novel β-carboline-cyanoisoflavone compound of the present invention in different tumor cells

[0078] The present invention uses the methyl tetrazolium blue colorimetric (MTT) method to evaluate the cytotoxicity and photodynamic therapy activity of the compound of the present invention against human lung cancer cell line A549, human colon cancer cell line HT29, mouse breast cancer cell line 4T1, and human normal colon epithelial cell line CCD841 in vitro toxicity test. First, a bottle of cells in good exponential growth phase was taken and 0.25% trypsin was added to digest the adherent cells to detach them. The solution was prepared into a liquid containing 2×10 4 ~4×10 4 The cell suspension was inoculated into a 96-well plate, 180 μL per well, and cultured in a constant temperature CO2 incubator for 24 hours. Dark group: Compounds I1-I3 of the present invention were dissolved in DMSO and diluted with PBS, and cultured for 24 hours. Light group: Compounds of the present invention were dissolved in DMSO and diluted with PBS, and incubated for 2 hours, and then irradiated with 520 nm (200 mW / cm 2 ) for 10 minutes and then incubate for 24 hours. Then, MTT was added to a 96-well plate and incubated in an incubator for 4 hours. The absorbance of each well was measured at 450 nm using an enzyme-linked immunosorbent assay (ELISA) and cell viability was calculated. Cell viability = OD value of the test group / OD value of the negative control group × 100%.

[0079] The compounds of the present invention were tested for their anti-proliferative activity on a series of tumor cells. 2+ As a negative control, the experimental results show (Table 2) that the compounds I1-I3 of the present invention have an inhibitory effect on the proliferation of A549, HT29 and 4T1 tumor cells, and the anti-proliferative activity is significantly enhanced after light irradiation. Among them, the photodynamic therapy activity of the compound I2 of the present invention is the most prominent, and the photodynamic therapy index PI is between 5 and 6. In addition, the compounds of the present invention can not only exert a photodynamic effect at the tumor site, but also selectively inhibit tumor cells, and have a smaller inhibitory effect on human normal colon cells CCD841 ( Figure 6 ).

[0080] Table 2: Comparison of the activities of novel β-carboline-cyanoisoflavone compounds in different tumor cells (IC 50 ,μM)

[0081]

[0082] ND: Not detected.

[0083] The embodiments of the present invention are described in detail above, but the contents described are only preferred embodiments of the present invention and should not be considered to limit the scope of the present invention. All equivalent changes and improvements made within the scope of the present invention should still fall within the scope of the patent coverage of the present invention.

Claims

1. A β-carboline-cyanoisoflavone compound, characterized in that: It has the structure shown in general formula I: ， Wherein, R is selected from one of H, N(Me)2, and N(Ph)2; and X is selected from one of S and Se.

2. The β-carboline-cyanoisoflavone compound according to claim 1, characterized in that: R=H or R=N(Ph)2; X is selected from S and Se.

3. The method for preparing the β-carboline-cyanoisoflavone compound according to claim 1 or 2, characterized in that The steps include: a). 1,9-dimethyl-6R-9H-pyrido[3,4-b]indole-3-carboxaldehyde and compound 2 are subjected to a condensation reaction in the presence of pyridine or piperidine to obtain a β-carboline-cyanoisoflavone compound I wherein R is H. ； or, a'). 1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde is brominated to obtain 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde, ； b'). The 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde is reacted with diphenylamine or dimethylamine under catalytic conditions to obtain compound 4, ； c '). Compound 4 and compound 2 are subjected to a condensation reaction in the presence of pyridine or piperidine to obtain R is N (Me) 2 or N (Ph) 2 β-carboline - cyanoisoflavone compound I, ； R is N(Me)2 or N(Ph)2, and X is selected from one of S and Se.

4. The method according to claim 3, characterized in that The steps include: a) Dissolving 1,9-dimethyl-6R-9H-pyrido[3,4-b]indole-3-carboxaldehyde and compound 2 in anhydrous ethanol, adding pyridine or piperidine as a base to carry out a condensation reaction to obtain a β-carboline-cyanoisoflavone compound I wherein R is H; or, a'). Dissolve 1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde in anhydrous THF, add N-bromosuccinimide, and react to obtain 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carbaldehyde; b'). The 6-bromo-1,9-dimethyl-9H-pyrido[3,4-b]indole-3-carboxaldehyde is reacted with diphenylamine or dimethylamine in the presence of palladium acetate, tri-tert-butylphosphine and cesium carbonate to give compound 4; c ') Compound 4 and compound 2 were dissolved in anhydrous ethanol, and 2 drops of pyridine or piperidine were added as a base to obtain R is N (Me) 2 or N (Ph) 2 β-carboline - cyano isoflavone compound I, R is N(Me)2 or N(Ph)2, and X is selected from one of S and Se.

5. Use of the β-carboline-cyanoisoflavone compound according to claim 1 or 2 in the preparation of a photosensitizer.

6. The use according to claim 5, characterized in that The photosensitizer generates active oxygen molecules under 520nm light excitation.

7. Use of the β-carboline-cyanoisoflavone compound according to claim 1 or 2 in the preparation of a photodynamic therapy drug, wherein the photodynamic therapy drug is an anti-tumor drug, and the tumor is colon cancer, lung cancer, or breast cancer.

8. Use of the β-carboline-cyanoisoflavone compound according to claim 1 or 2 in the preparation of a drug having selective activity of inhibiting tumor cell proliferation, wherein the tumor is colon cancer, lung cancer, or breast cancer.

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