Indole-containing formononetin derivative as well as preparation method and application thereof

Abstract

The invention discloses a formononetin derivative containing indole as well as a preparation method and application of the formononetin derivative, and belongs to the technical field of pesticide synthesis. According to the invention, an indole group with good biological activity is introduced into a formononetin structure, a series of formononetin derivatives containing indole are designed and synthesized, and the synthesized formononetin derivatives containing indole are subjected to plant pathogen inhibition activity tests. It is found that the derivative can effectively inhibit various plant pathogenic fungi, and especially shows the strongest inhibitory activity on Phomopsis kiwifruit.

Description

Technical Field

[0001] This invention belongs to the field of pesticide synthesis technology, specifically relating to an indole-containing gentianin derivative and its preparation method and application. Background Technology

[0002] Plant diseases have long affected crop yield and quality, causing severe losses to the food economy. Their rapid spread and susceptibility to pesticide resistance pose a serious challenge to chemical control. Furthermore, long-term reliance on traditional chemical fungicides has not only led to widespread pathogen resistance but also resulted in environmental residues and ecological security issues. Therefore, developing novel antimicrobial agents that are highly effective, low in toxicity, environmentally compatible, and less prone to resistance development is an urgent need and an important research direction in the field of sustainable agricultural development. Developing highly effective and low-toxicity plant-derived green pesticides is considered a highly promising approach.

[0003] Among numerous plant-derived bioactive molecules, isoflavones have attracted attention due to their broad bioactivity and low ecotoxicity. Arganin (…) Formononetin 7-Hydroxy-4'-methoxyisoflavone (HH2O) is an important isoflavone found in legumes, widely distributed in various medicinal plants such as Astragalus membranaceus, red clover, and kudzu root. Modern pharmacological studies have confirmed that it possesses various pharmacological effects, including antioxidant, anti-inflammatory, anticancer, antitumor, and anti-lipid peroxidation properties. It also has effects such as improving atherosclerosis, inhibiting abnormal proliferation of vascular smooth muscle cells, regulating glucose and lipid metabolism, anti-osteoporosis, and anti-aging. In 2021, Cui et al. reported that strychnine has significant antiviral activity against feline calicivirus (FCV), with a minimum inhibitory concentration (MIC) of [missing value]. 50 The value is 13.6. μ mol / L. In 2023, Jia et al. synthesized a series of gentianin derivatives and tested their anticancer and antitumor activities. The results showed that some compounds exhibited strong inhibitory activity against non-small cell lung cancer A549 cells, with a minimum inhibitory concentration (IC50) of 100 mol / L. 50 The value is 0.87 μ mol / L. In 2025, Luo et al. synthesized a series of strychnine derivatives and evaluated their neuroprotective activity and mechanism of action in the N2a / APP695 cell model. The results showed that some compounds could clear abnormal protein deposits and reduce neurotoxicity. In 2025, Fu et al. synthesized a series of strychnine derivatives and conducted antibacterial activity tests and mechanism of action studies. The results showed that most compounds were effective against Phytophthora capsici (…). Phytophthora capsica It exhibits good antibacterial activity, with a minimum inhibitory concentration (EC50) of 100 μg / mL. 50 The value is 4.2. μg / mL. Numerous literature reports focus on pharmaceutical targets, but research reports on gentianin and its derivatives targeting plant pathogens in the pesticide field are relatively few, indicating significant room for exploration in structural optimization and activity enhancement.

[0004] Indole, a nitrogen-containing aromatic heterocyclic compound, is a core skeleton in natural products and drug molecules. This structure is widely found in fundamental biological substances (such as the amino acid tryptophan, the neurotransmitter serotonin, and the plant hormone indole-3-acetic acid). In medicinal chemistry, indole exhibits multiple pharmacological activities, including antibacterial, antiviral, and antitumor effects, due to its unique chemical structure and broad biological activity. In pesticide development, this structure has also been proven to endow molecules with excellent bactericidal and insecticidal properties. Its abundant structural modification sites and ease of derivatization make it an important pharmacophore for optimizing the activity, selectivity, and physicochemical properties of lead compounds.

[0005] In summary, no indole has been found to be introduced into the structure of genistein to synthesize indole-containing genistein derivatives, nor have indole-containing genistein derivatives been used in agricultural activity studies. Summary of the Invention

[0006] The purpose of this invention is to provide an indole-containing genistein derivative, its preparation method, and its application. The provided indole-containing genistein derivative can be used to inhibit plant pathogenic fungi, especially *Actinidia kiwifruit*.

[0007] To achieve the above objectives, the present invention provides the following technical solution: One of the technical solutions of this invention is to provide an indole-containing strychnosine derivative, the structure of which is shown in the following formula:

[0008] In the above formula, R is independently selected from H, one or more halogens, one or more nitro groups, one or more C1-C6 alkyl groups, and one C1-C6 alkoxy group.

[0009] Preferably, the halogen is F, Cl, or Br.

[0010] The second technical solution of the present invention provides a method for preparing the above-mentioned indole-containing strychnosine derivative, the steps of which include: Using indole and epoxybromopropane as raw materials and sodium hydride as catalyst, the reaction was carried out under reflux in a solvent. After the reaction was completed, the mixture was extracted with dichloromethane and the extract was evaporated to dryness to obtain intermediate a. The structural formula of the epoxybromopropane is: ; The structural formula of intermediate a is: R is independently selected from H, one or more halogens, one or more nitro groups, one or more C1-C6 alkyl groups, and one C1-C6 alkoxy group. Preferably, the halogen is F, Cl, or Br.

[0011] (2) Using gentianin and epoxybromopropane as raw materials and anhydrous potassium carbonate as catalyst, the reaction was carried out at room temperature. After the reaction was completed, ice water was added to precipitate the product. The product was filtered, and the residue was cleaned of impurities to obtain intermediate b. The structural formula of intermediate b is: ; (3) Using intermediate b and piperazine as raw materials and anhydrous potassium carbonate as catalyst, the reaction was carried out in a solvent under reflux. After the reaction was completed, ice water was added to precipitate the product. The product was filtered, and the residue was cleaned to obtain intermediate c. The structural formula of the intermediate c is: ; (4) Using intermediates c and a as raw materials and anhydrous potassium carbonate as catalyst, the mixture is heated under reflux in a solvent. After the reaction is complete, ice water is added to precipitate the product. The product is filtered, and the residue is cleaned of impurities to obtain the indole-containing gentianin derivative.

[0012] Preferably, the molar ratio of indole, epoxybromopropane, and sodium hydride in step (1) is 12.8:25.6:25.6; the heating temperature is 80°C; the reaction time is 2-5 h; and the solvent is N,N-dimethylformamide.

[0013] Preferably, in step (2), the molar ratio of styrax styrax, epoxybromopropane, and anhydrous potassium carbonate is 18.6:37.3:55.9; the reaction time is 1 day; the solvent is N,N-dimethylformamide; the impurity removal step includes: washing the filter residue sequentially with water and petroleum ether, then allowing it to stand and filter to complete the washing.

[0014] Preferably, in step (3), the molar ratio of intermediate b, piperazine, and anhydrous potassium carbonate is 6.2:20.4:18.5; the reaction temperature is 80°C; the reaction time is 2-4 hours; the solvent is isopropanol; and the impurity removal step includes: washing the filter residue sequentially with water and petroleum ether, then allowing it to stand and filter to complete the washing.

[0015] Preferably, in step (4), the molar ratio of intermediate c, intermediate a and anhydrous potassium carbonate is 2.44:4.4:7.3; the heating reaction temperature is 80°C; the reaction time is 2-4 h; the solvent is isopropanol; the impurity removal step includes: washing the filter residue sequentially with water and petroleum ether, then allowing it to stand and filter to complete the washing.

[0016] More preferably, step (4) further includes a purification step after heating and reflux. The purification step specifically includes: pouring the reaction solution after heating and reflux into ice water to disperse the reaction solution and precipitate solids. After the solids are precipitated, the step further includes a filtration and washing step, washing with water and petroleum ether respectively; column chromatography to complete the purification. The eluent used for column chromatography is a mixture of dichloromethane and methanol in a volume ratio of 20:1, and then slurrying. The solution used for slurrying is a mixture of petroleum ether and dichloromethane in a volume ratio of 50:1.

[0017] The third technical solution of the present invention provides the application of the above-mentioned indole-containing strychnosine derivative in the preparation of drugs for inhibiting plant pathogenic fungi.

[0018] Preferably, the plant pathogenic fungi include *Actinidia kiwifruit* (Ps); *Phytophthora capsulatum* (Pc); *Anthracnose causal agent* (Cg); *Rhizoctonia solani* (Rs); *Fusarium graminearum* (Fg); *Black spot causal agent* (Ab); *Fusarium wilt causal agent* (Foc); *Fusarium wilt causal agent* (Fo); and *Sclerotinia sclerotiorum* (Ss).

[0019] The beneficial technical effects of the present invention are as follows: This invention provides an indole-containing genistein derivative, its preparation method, and its application. The invention introduces a bioactive indole group into the genistein structure, designs and synthesizes a series of indole-containing genistein derivatives, and tests the inhibitory activity of the synthesized indole-containing genistein derivatives against plant pathogens. The results show that these derivatives can effectively inhibit various plant pathogenic fungi, especially exhibiting the strongest inhibitory activity against *Actinidia kiwifruit*. Detailed Implementation

[0020] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention. It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the present invention.

[0021] Furthermore, regarding the numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Any stated value or intermediate value within a stated range, as well as each smaller range between any other stated value or intermediate value within said range, are also included in this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.

[0022] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar to or equivalent to those described herein may be used in the implementation or testing of this invention.

[0023] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.

[0024] One of the technical objectives of this invention is to provide an indole-containing strychnosine derivative, the structure of which is shown in the following formula:

[0025] In the above formula, R is independently selected from H, one or more halogens, one or more nitro groups, one or more C1-C6 alkyl groups, and one C1-C6 alkoxy group.

[0026] Preferably, the halogen is F, Cl, or Br.

[0027] The second technical objective of this invention is to provide a method for preparing the above-mentioned indole-containing strychnosine derivative, the steps of which include: (1) Using indole and epoxybromopropane as raw materials, the reaction is carried out in a solvent under alkaline conditions at 80°C for 2-5 hours. After the reaction is completed, intermediate a is prepared by extraction with dichloromethane, drying and rotary evaporation under reduced pressure. The reaction formula is as follows:

[0028] R is independently selected from H, one or more halogens, one or more nitro groups, one or more C1-C6 alkyl groups, and one C1-C6 alkoxy group. Preferably, the halogen is F, Cl, or Br.

[0029] In some embodiments, the solvent is N,N-dimethylformamide; the alkaline conditions are provided by sodium hydride; the reaction is further performed by dichloromethane extraction and rotary evaporation under reduced pressure; and the molar ratio of indole, epichlorohydride, and sodium hydride is 12.8:25.6:25.6. (2) Using gentianin and epoxybromopropane as raw materials and anhydrous potassium carbonate as catalyst, intermediate b was prepared by reacting at room temperature in N-N-dimethylformamide solvent for 1 day. The reaction formula is as follows:

[0030] In some embodiments, after the reaction is completed, the reaction solution is further dispersed with ice water to precipitate solids; after the solids are precipitated, the reaction solution is further filtered and washed; the washing is performed with water and petroleum ether respectively; wherein the molar ratio of gentianin, epoxybromopropane and anhydrous potassium carbonate is 18.6:37.3:55.9. (3) Using intermediate b and piperazine as raw materials and anhydrous potassium carbonate as catalyst, intermediate c was prepared by reacting in N-N-dimethylformamide solvent at 80°C for 2-4 hours; The reaction formula is as follows:

[0031] In some embodiments, after the reaction is completed, the reaction solution is further dispersed with ice water to precipitate a solid; after the solid is precipitated, the reaction solution is further filtered and washed; the washing is performed with water and petroleum ether respectively; wherein the molar ratio of intermediate b, piperazine, and anhydrous potassium carbonate is 6.2:20.4:18.5. (4) Using intermediates c and a as raw materials and anhydrous potassium carbonate as catalyst, indole-containing styracin derivatives were prepared by heating and refluxing in isopropanol solvent at 80°C. The reaction formula is as follows:

[0032] In some embodiments, the reflux reaction time is 2-4 hours; after the reaction, the reaction system is further dispersed in ice water to precipitate solids, followed by filtration, washing, column chromatography, and slurry preparation. The eluent used for column chromatography is a mixture of dichloromethane and methanol in a volume ratio of 20:1, and the slurry preparation uses a mixture of petroleum ether and dichloromethane in a volume ratio of 50:1. The molar ratio of intermediate c, intermediate a, and anhydrous potassium carbonate is 2.44:4.4:7.3.

[0033] The third technical objective of this invention is to provide the application of the above-mentioned indole-containing strychnosine derivative in the preparation of drugs for inhibiting plant pathogenic fungi.

[0034] To achieve the above-mentioned technical objectives, the present invention provides the following embodiments.

[0035] Example 1 7-[2-hydroxy-3-(4-(2-hydroxy-2-(1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D1), the steps are as follows: (1) Synthesis of 1-(epoxyethylenemethyl)-1H-indole: Indole (1.5 g, 12.8 mmol), sodium hydride (0.6 g, 25.6 mmol), and 50 mL of N,N-dimethylformamide were added to a 100 mL three-necked flask and heated to 80 °C. After stirring for 0.5 h, epoxybromopropane (2.1 mL, 25.6 mmol) was slowly added and reacted for 3 h. The mixture was extracted with dichloromethane, and the organic phase was collected. The solvent was removed by rotary evaporation under reduced pressure to obtain an oily substance with a yield of 81.1%.

[0036] (2) Synthesis of 7-(epoxyethylenemethoxy)-4-(4-methoxyphenyl)-2H-chromen-2-one: Strigolamine (5 g, 18.64 mmol) and anhydrous potassium carbonate (7.7 g, 55.9 mmol) were added to 500 mL of N,N-dimethylformamide solution. After stirring at room temperature for 1 h, epichlorohydrin (3 mL, 37.28 mmol) was added to the system, and the reaction was allowed to proceed at room temperature for 1 day. After the reaction was complete, the mixture was dispersed in 800 mL of ice water, precipitating a large amount of solid. The solid was filtered, washed several times with water and petroleum ether, dried, and filtered again to obtain a white solid with a yield of 93.8%.

[0037] (3) Preparation of 7-[2-hydroxy-3-(piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one: Piperazine (2.63 g, 20.4 mmol) and anhydrous potassium carbonate (2.56 g, 18.5 mmol) were dissolved in 50 mL of isopropanol in a 100 mL single-necked flask. After stirring under reflux at 80 °C for 0.5 h, the product (2 g, 6.2 mmol) from step (2) was added to the system and reacted for 2 h. After the reaction was completed, the product was dispersed in 500 mL of ice water, and a large amount of solid precipitated. The solid was filtered, washed several times with water and petroleum ether, dried, and filtered again to obtain a white-yellow solid with a yield of 85.7%.

[0038] (4) Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one: The product from step 3 (1 g, 2.4 mmol), anhydrous K2CO3 (1 g, 7.31 mmol), and 50 mL of NN-dimethylformamide were added to a 50 mL round-bottom flask. After reflux and stirring at 80 °C for 0.5 h, 1-(epoxyethylenemethyl)-1H-indole (0.76 g, The reaction was carried out with 4.4 mmol of dichloromethane (4.4 mmol) for 2 h. After the reaction was completed, the system was dispersed in 500 mL of ice water, and a large amount of solid precipitated. The solid was filtered, washed several times with water and petroleum ether, dried, filtered again, and then subjected to column chromatography (dichloromethane:methanol = 20:1, v / v) and pulping (petroleum ether:dichloromethane = 50:1, v / v) to obtain the target compound with a yield of 34%.

[0039] Example 2: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-bromo-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D2), the steps were the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 5-bromo-1-(epoxyethylenemethyl)-1H-indole. Yield: 51%.

[0040] Example 3: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-chloro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D3), the steps were the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 5-chloro-1-(epoxyethylenemethyl)-1H-indole. Yield: 34%.

[0041] Example 4: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-methoxy-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D4), the steps were the same as in Example 1, except that in step (4), 1-(epoxyethylenemethyl)-1H-indol was replaced with an equimolar amount of 5-methoxy-1-(epoxyethylenemethyl)-1H-indol. Yield: 48%.

[0042] Example 5: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-fluoro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D5), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 5-fluoro-1-(epoxyethylenemethyl)-1H-indole. Yield: 40%.

[0043] Example 6: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-nitro-1H-indole-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D6), the steps were the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 5-nitro-1-(epoxyethylenemethyl)-1H-indole. Yield: 31%.

[0044] Example 7: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(5-methyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D7), the steps were the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 5-methyl-1-(epoxyethylenemethyl)-1H-indole. Yield: 40%.

[0045] Example 8: Synthesis of [2-hydroxy-3-(4-(2-hydroxy-2-(5,6-dichloro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D8), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 5,6-dichloro-1-(epoxyethylenemethyl)-1H-indol. Yield: 39%.

[0046] Example 9: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-chloro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D9), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 6-chloro-1-(epoxyethylenemethyl)-1H-indole. Yield: 38%.

[0047] Example 10: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-methoxy-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D10), the procedure was the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 6-methoxy-1-(epoxyethylenemethyl)-1H-indol. Yield: 41%.

[0048] Example 11: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(3-methyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D11), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 3-methyl-1-(epoxyethylenemethyl)-1H-indol. Yield: 54%.

[0049] Example 12: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(2,3-dimethyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D12), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 2,3-dimethyl-1-(epoxyethylenemethyl)-1H-indol. Yield: 39%.

[0050] Example 13: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-bromo-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D13), the procedure was the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 6-bromo-1-(epoxyethylenemethyl)-1H-indol. Yield: 41%.

[0051] Example 14: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-fluoro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D14), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 6-fluoro-1-(epoxyethylenemethyl)-1H-indole. Yield: 33%.

[0052] Example 15: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-nitro-1H-indole-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D15), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 6-nitro-1-(epoxyethylenemethyl)-1H-indole. Yield: 47%.

[0053] Example 16: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(4-chloro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D16), the procedure was the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indole in step (4) was replaced with an equimolar amount of 4-chloro-1-(epoxyethylenemethyl)-1H-indole. Yield: 42%.

[0054] Example 17: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(4-bromo-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D17), the procedure was the same as in Example 1, except that 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 4-bromo-1-(epoxyethylenemethyl)-1H-indol. Yield: 47%.

[0055] Example 18: Synthesis of [2-hydroxy-3-(4-(2-hydroxy-2-(4-fluoro-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D18), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 4-fluoro-1-(epoxyethylenemethyl)-1H-indol. Yield: 58%.

[0056] Example 19: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(4-methoxy-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D19), the procedure was the same as in Example 1, except that in step (4), 1-(epoxyethylenemethyl)-1H-indol was replaced with an equimolar amount of 4-methoxy-1-(epoxyethylenemethyl)-1H-indol. Yield: 42%.

[0057] Example 20: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(4-methyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D20), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 4-methyl-1-(epoxyethylenemethyl)-1H-indol. Yield: 54%.

[0058] Example 21: Synthesis of 7-[2-hydroxy-3-(4-(2-hydroxy-2-(6-methyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D21), the procedure was the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 6-methyl-1-(epoxyethylenemethyl)-1H-indol. Yield: 30%.

[0059] Example 22: Synthesis of [2-hydroxy-3-(4-(2-hydroxy-2-(7-methyl-1H-indol-1-yl)ethyl)piperazin-1-yl)propoxy]-4-(4-methoxyphenyl)-2H-chromen-2-one (compound number D22), the steps were the same as in Example 1, except that the 1-(epoxyethylenemethyl)-1H-indol in step (4) was replaced with an equimolar amount of 7-methyl-1-(epoxyethylenemethyl)-1H-indol. Yield: 42%.

[0060] The physicochemical properties and mass spectrometry data of the indole-containing genistein derivatives synthesized in Examples 1-22 are shown in Table 1, and the proton nuclear magnetic resonance spectra (NMR spectra) are also shown. 1 H NMR and carbon spectroscopy 13 The C NMR data are shown in Table 2.

[0061] Table 1. Physicochemical properties and mass spectrometry data of the target compounds compound Yield (%) Properties Melting point (°C) HRMS, m / z (calcd.) D1 34 White solid 92.6-93.3 <![CDATA[584.27551(584.27643)[M+H] + ]]> D2 51 White solid 84.3-85.3 <![CDATA[662.18602(662.18793)[M+H] + ]]> D3 34 White solid 78.8-79.5 <![CDATA[618.23654(618.23785)[M+H] + ]]> D4 48 White solid 139.6-140.3 <![CDATA[614.28608(614.28699)[M+H] + ]]> D5 40 White solid 97.2-98.3 <![CDATA[602.26609(602.26709)[M+H] + ]]> D6 31 Yellow solid 77.6-78.3 <![CDATA[629.26059(629.26178)[M+H] + ]]> D7 40 White solid 79.3-80.7 <![CDATA[598.29116(598.29175)[M+H] + ]]> D8 39 White solid 77.8-80.7 <![CDATA[652.19757(652.19879)[M+H] + ]]> D9 38 White solid 77.8-79.2 <![CDATA[618.23654(618.23712)[M+H] + ]]> D10 41 pink solid 63.1-64.3 <![CDATA[614.28608(614.28699)[M+H] + ]]> D11 54 White solid 139.8-140.5 <![CDATA[598.29116(598.29199)[M+H] + ]]> D12 39 White solid 110.1-111.8 <![CDATA[612.30681(612.30804)[M+H] + ]]> D13 41 Yellow solid 80.6-81.2 <![CDATA[662.18602(662.18738)[M+H] + ]]> D14 33 White solid 75.1-76.3 <![CDATA[602.26609(602.26685)[M+H] + ]]> D15 47 Yellow solid 98.4-99.5 <![CDATA[629.26059(629.26270)[M+H] + ]]> D16 42 White solid 190.3-191.6 <![CDATA[618.23654(618.23785)[M+H] + ]]> D17 47 White solid 77.9-79.1 <![CDATA[662.18602(662.18750)[M+H] + ]]> D18 58 White solid 61.4-62.3 <![CDATA[602.26609(602.26727)[M+H] + ]]> D19 42 Yellow solid 150.2-151.7 <![CDATA[614.28608(614.28705)[M+H] + <!-- 8 -->]]> D20 54 White solid 109.7-110.9 <![CDATA[598.29116(598.29218)[M+H] + ]]> D21 30 White solid 126.1-127.6 <![CDATA[598.29116(598.29254)[M+H] + ]]> D22 42 pink solid 90.3-91.4 <![CDATA[598.29116(598.29205)[M+H] + ]]> Table 2. NMR spectral data of the target compound compound <![CDATA[ 1 H NMR and 13 1C NMR (TMS as internal standard) D1 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (d, J = 0.8 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.51 (m, 3H), 7.47 – 7.45 (m, 1H),7.32 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.12 –7.08 (m, 2H), 7.01 – 6.97 (m, 3H), 6.40 (dd, J = 3.1, 0.8 Hz,1H), 4.95 (dd, J = 48.4, 4.6 Hz, 2H), 4.27 (dd, J = 14.3, 3.8Hz, 1H), 4.16 – 4.13 (m, 1H), 4.09 – 3.99 (m, 3H), 3.96 –3.92 (m, 1H), 3.79 (s, 3H), 2.50 – 2.44 (m, 6H), 2.43 – 2.32(m, 4H), 2.22 (d, J = 6.3 Hz, 2H). 13 C NMR (126 MHz, DMSO- D 6)δ 175.16, 163.75, 159.51, 157.93, 154.02, 136.74, 130.62,130.17, 128.46, 127.48, 124.59, 123.88, 121.24, 120.72,119.24, 118.04, 115.65, 114.13, 110.57, 101.63, 100.69,72.51, 67.73, 66.79, 62.01, 61.41, 55.67, 54.10 (d, J = 9.7Hz), 50.56.]]> D2 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (d, J = 0.8 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.70 (d, J = 1.0 Hz, 1H), 7.54 – 7.51 (m,2H), 7.46 (d, J = 8.8 Hz, 1H), 7.38 (d, J = 3.1 Hz, 1H), 7.21(dd, J = 8.7, 2.0 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.09(dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m, 2H), 6.40 (dd, J =3.1, 0.8 Hz, 1H), 4.96 (dd, J = 35.0, 4.2 Hz, 2H), 4.25 (dd, J = 14.3, 3.6 Hz, 1H), 4.14 (dd, J = 9.8, 3.0 Hz, 1H), 4.10 –3.99 (m, 3H), 3.96 – 3.91 (m, 1H), 3.79 (s, 3H), 2.50 – 2.42(m, 6H), 2.39 (dd, J = 12.8, 5.8 Hz, 4H), 2.21 – 2.15 (m,2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.75, 159.51,157.93, 154.02, 135.62, 131.74, 130.62, 130.26, 127.48,124.59, 123.88, 123.65, 122.84, 118.04, 115.65, 114.14,112.82, 111.90, 101.62, 100.47, 72.51, 67.67, 66.81, 61.85,61.41, 55.67, 54.11, 50.66.<!-- 9 --> ]]> D3 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (d, J = 0.7 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.56 (d, J = 2.0 Hz, 1H), 7.54 – 7.49 (m,3H), 7.39 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.11– 7.08 (m, 2H), 7.01 – 6.98 (m, 2H), 6.40 (dd, J = 3.1, 0.8Hz, 1H), 4.96 (dd, J = 36.7, 4.6 Hz, 2H), 4.25 (dd, J = 14.3,3.6 Hz, 1H), 4.17 – 4.13 (m, 1H), 4.11 – 3.99 (m, 3H), 3.95 –3.91 (m, 1H), 3.79 (s, 3H), 2.50 – 2.43 (m, 6H), 2.39 (dd, J = 12.8, 5.9 Hz, 4H), 2.23 – 2.16 (m, 2H). 13 C NMR (126 MHz,DMSO- D 6) δ 175.15, 163.74, 159.51, 157.93, 154.01, 135.38,131.89, 130.61, 129.52, 127.47, 124.59, 123.90 (d, J = 6.8Hz), 121.13, 119.79, 118.04, 115.64, 114.13, 112.32, 101.62,100.55, 72.51, 67.67, 61.85, 61.39, 55.67, 54.10, 50.69.]]> D4 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (d, J = 1.0 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.35 (d, J = 8.9 Hz,1H), 7.26 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.09(dd, J = 8.9, 2.4 Hz, 1H), 7.02 – 6.98 (m, 3H), 6.75 (dd, J =8.9, 2.5 Hz, 1H), 6.31 (dd, J = 3.0, 0.8 Hz, 1H), 4.93 (dd, J = 58.4, 4.6 Hz, 2H), 4.21 (dd, J = 14.3, 3.8 Hz, 1H), 4.16 –4.12 (m, 1H), 4.05 – 3.98 (m, 3H), 3.94 – 3.89 (m, 1H), 3.79(s, 3H), 3.73 (s, 3H), 2.50 – 2.43 (m, 6H), 2.39 (dd, J =12.4, 5.4 Hz, 4H), 2.22 – 2.16 (m, 2H). 13 C NMR (126 MHz,DMSO- D 6) δ 175.16, 163.74, 159.51, 157.93, 154.01, 153.77,132.06, 130.58 (d, J = 7.9 Hz), 128.78, 127.47, 124.59,123.87, 118.04, 115.64, 114.13, 111.31 (d, J = 10.9 Hz),102.39, 101.62, 100.36, 72.51, 67.76, 66.79, 61.96, 61.41,55.80, 55.67, 54.09 (d, J = 9.9 Hz), 50.70. <!-- 10 -->]]> D5 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (d, J = 0.5 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.49 (m, 3H), 7.33 – 7.30 (m, 2H),7.17 (d, J = 2.4 Hz, 1H), 7.09 (dd, J = 8.9, 2.4 Hz, 1H),7.01 – 6.98 (m, 2H), 6.85 (ddd, J = 9.7, 8.6, 2.3 Hz, 1H),6.42 (dd, J = 3.1, 0.8 Hz, 1H), 4.95 (dd, J = 40.6, 4.5 Hz,2H), 4.23-4.19 (m, 1H), 4.15 (dd, J = 9.7, 2.9 Hz, 1H), 4.09– 3.99 (m, 3H), 3.96 – 3.92 (m, 1H), 3.79 (s, 3H), 2.50 –2.43 (m, 6H), 2.43 – 2.28 (m, 4H), 2.22 – 2.16 (m, 2H). 13 CNMR (126 MHz, DMSO- D 6) δ 175.16, 163.75, 160.12, 159.51,158.26, 157.93, 154.01, 136.99, 130.91, 130.61, 127.47,125.08, 124.59, 123.87, 121.63, 118.04, 115.64, 114.13,107.76, 107.57, 101.62, 101.03, 97.24, 97.03, 72.50, 67.71,66.81, 61.72, 61.42, 55.66, 54.11, 50.60. 19 F NMR (471 MHz,DMSO- D 6) δ -121.93.]]> D6 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.56 (d, J = 2.3 Hz, 1H), 8.41 (s,1H), 8.04 – 8.00 (m, 2H), 7.68 (d, J = 9.2 Hz, 1H), 7.59 (d, J = 3.2 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.16 (d, J = 2.4 Hz,1H), 7.09 (dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m, 2H),6.74 (dd, J = 3.2, 0.8 Hz, 1H), 5.01 – 4.98 (m, 2H), 4.33(dd, J = 14.4, 3.5 Hz, 1H), 4.21 – 4.13 (m, 2H), 4.05 – 3.97(m, 3H), 3.78 (s, 3H), 2.50 – 2.43 (m, 6H), 2.39 (dd, J =12.8, 5.8 Hz, 4H), 2.25 – 2.17 (m, 2H). 13 C NMR (126 MHz,DMSO- D 6) δ 175.15, 163.74, 159.51, 157.92, 154.01, 140.98,139.99, 134.08, 130.61, 127.68, 127.47, 124.59, 123.87,117.97 (d, J = 18.5 Hz), 116.60, 115.63, 114.13, 111.43,103.82, 101.62, 72.50, 67.61, 66.80, 61.76, 61.40, 55.66,54.07, 50.94. <!-- 11 -->]]> D7 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (dd, J = 8.9,1.4 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.34 (d, J = 8.4 Hz, 1H),7.29 – 7.24 (m, 2H), 7.17 (s, 1H), 7.11 – 7.07 (m, 1H), 7.01– 6.98 (m, 2H), 6.92 (d, J = 8.4 Hz, 1H), 6.29 (d, J = 3.0Hz, 1H), 4.93 (dd, J = 59.8, 4.6 Hz, 2H), 4.22 (dd, J = 14.4,3.7 Hz, 1H), 4.14 (d, J = 8.2 Hz, 1H), 4.06 – 3.99 (m, 3H),3.94 – 3.89 (m, 1H), 3.78 (s, 3H), 2.50 – 2.44 (m, 6H), 2.44– 2.37 (m, 3H), 2.35 (s, 4H), 2.20 (d, J = 6.3 Hz, 2H). 13 CNMR (126 MHz, DMSO- D 6) δ 175.16, 163.74, 159.51, 157.93,154.01, 135.21, 130.61, 130.12, 128.70, 127.66, 127.48,124.59, 123.88, 122.83, 120.33, 118.05, 115.64, 114.13,110.26, 101.62, 100.14, 72.51, 67.76, 66.80, 61.98, 61.40,55.67, 54.13, 50.59, 21.64.]]> D8 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.82 (s, 1H), 7.77 (s, 1H), 7.53 – 7.51 (m, 2H), 7.43(d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.3 Hz, 1H), 7.09 (dd, J =8.9, 2.3 Hz, 1H), 7.00 – 6.98 (m, 2H), 6.44 (d, J = 3.1 Hz,1H), 4.98 (dd, J = 17.4, 4.1 Hz, 2H), 4.25 – 4.21 (m, 1H),4.16 – 4.11 (m, 2H), 4.05 – 4.00 (m, 2H), 3.96 – 3.92 (m,1H), 3.78 (s, 3H), 2.50 – 2.42 (m, 6H), 2.42 – 2.26 (m, 4H),2.18 – 2.10 (m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16,163.74, 159.51, 157.93, 154.01, 136.04, 132.94, 130.61,128.22, 127.47, 124.59, 123.87, 123.62, 121.69 (d, J = 21.0Hz), 118.04, 115.64, 114.13, 112.81, 101.62, 100.78, 72.48,67.62, 61.42, 55.66, 54.05.]]> D9 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.61 (s, 1H), 7.54 – 7.51 (m, 3H), 7.35 (d, J = 3.1 Hz,1H), 7.17 (d, J = 2.4 Hz, 1H), 7.09 (dd, J = 8.9, 2.4 Hz,1H), 7.01 – 6.98 (m, 3H), 6.44 (dd, J = 3.1, 0.8 Hz, 1H),4.97 (dd, J = 27.7, 4.5 Hz, 2H), 4.25 – 4.21 (m, 1H), 4.16 –4.08 (m, 2H), 4.05 – 3.98 (m, 2H), 3.96 – 3.91 (m, 1H), 3.79(s, 3H), 2.50 – 2.45 (m, 6H), 2.40 (dd, J = 12.8, 5.7 Hz,4H), 2.21 – 2.12 (m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16,163.74, 159.51, 157.93, 154.01, 137.40, 131.39, 130.61,127.47, 127.12, 126.15, 124.59, 123.87, 121.97, 119.51,118.04, 115.64, 114.13, 110.77, 101.62, 101.10, 72.49, 67.74,66.81, 61.49 (d, J = 15.8 Hz), 55.66, 54.11, 50.43. <!-- 12 -->]]> D10 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (d, J = 0.8 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.38 (dd, J = 8.6, 1.1Hz, 1H), 7.17 (dd, J = 4.2, 2.8 Hz, 2H), 7.09 (dd, J = 8.9,2.4 Hz, 1H), 7.01 – 6.96 (m, 3H), 6.65 (dd, J = 8.6, 2.2 Hz,1H), 6.31 (dd, J = 3.2, 0.8 Hz, 1H), 4.94 (dd, J = 50.8, 4.5Hz, 2H), 4.22 (dd, J = 14.2, 3.6 Hz, 1H), 4.16 – 4.12 (m,1H), 4.04 – 3.97 (m, 3H), 3.96 – 3.91 (m, 1H), 3.79 (s, 3H),3.78 (s, 3H), 2.50 – 2.44 (m, 6H), 2.44 – 2.30 (m, 4H), 2.25(d, J = 6.3 Hz, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16,163.74, 159.51, 157.93, 155.88, 154.01, 137.48, 130.61,128.93, 127.47, 124.59, 123.88, 122.64, 121.25, 118.04,115.64, 114.13, 109.34, 101.62, 100.67, 94.01, 72.49, 67.75,66.79, 62.04, 61.40, 55.72 (d, J = 14.4 Hz), 54.11, 50.57.]]> D11 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 2H), 7.45 (d, J = 7.6 Hz, 1H), 7.39 (d, J = 8.3 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.10 – 7.07 (m,3H), 7.01 – 6.96 (m, 3H), 4.93 (dd, J = 65.9, 4.6 Hz, 2H),4.19 (dd, J = 14.3, 3.7 Hz, 1H), 4.14 (dd, J = 9.7, 2.9 Hz,1H), 4.04 – 3.96 (m, 3H), 3.93 – 3.89 (m, 1H), 3.79 (s, 3H),2.50 – 2.44 (m, 6H), 2.43 – 2.32 (m, 4H), 2.23 (d, J = 1.0Hz, 3H), 2.21 (d, J = 6.3 Hz, 2H). 13 C NMR (126 MHz, DMSO- D 6)δ 175.16, 163.75, 159.51, 157.93, 154.01, 137.02, 130.61,128.62, 127.73, 127.47, 124.59, 123.87, 121.24, 118.86,118.54, 118.04, 115.64, 114.13, 110.30, 108.84, 101.62,72.51, 67.84, 66.80, 62.04, 61.42, 55.67, 54.10 (d, J = 10.9Hz), 50.33, 10.00.]]> D12 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 2H), 7.35 (dd, J = 18.2, 7.6 Hz, 2H),7.17 (d, J = 2.4 Hz, 1H), 7.10 (dd, J = 8.9, 2.4 Hz, 1H),7.01 – 6.98 (m, 3H), 6.96 – 6.92 (m, 1H), 4.91 (dd, J = 83.4,4.0 Hz, 2H), 4.23 (dd, J = 14.7, 3.3 Hz, 1H), 4.15 (dd, J =7.8, 2.6 Hz, 1H), 4.03 (m, 2H), 3.94 (dd, J = 14.8, 7.8 Hz,1H), 3.84 (s, 1H), 3.79 (s, 3H), 2.50 – 2.45 (m, 6H), 2.45 –2.35 (m, 4H), 2.35 (s, 3H), 2.33 – 2.21 (m, 2H), 2.17 (s,3H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.75, 159.52,157.93, 154.01, 136.52, 133.84, 130.61, 128.61, 127.48,124.59, 123.88, 120.37, 118.60, 118.05, 117.86, 115.64,114.13, 109.73, 105.43, 101.63, 72.50, 68.18, 66.80, 62.69,61.41, 55.66, 54.17, 48.31, 10.77, 9.29. <!-- 13 -->]]> D13 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.74 (s, 1H), 7.54 – 7.51 (m, 2H), 7.47 (d, J = 8.4 Hz,1H), 7.34 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.12– 7.08 (m, 2H), 7.01 – 6.98 (m, 2H), 6.44 (dd, J = 3.1, 0.8Hz, 1H), 4.97 (dd, J = 25.1, 4.5 Hz, 2H), 4.23 (dd, J = 14.4,3.7 Hz, 1H), 4.16 – 4.09 (m, 2H), 4.05 – 3.99 (m, 2H), 3.95 –3.91 (m, 1H), 3.79 (s, 3H), 2.50 – 2.44 (m, 6H), 2.40 (dd, J = 12.7, 5.8 Hz, 4H), 2.20 – 2.13 (m, 2H). 13 C NMR (126 MHz,DMSO- D 6) δ 175.16, 163.75, 159.51, 157.93, 154.01, 137.86,131.31, 130.61, 127.42 (d, J = 14.1 Hz), 124.59, 123.88,122.37, 122.06, 118.04, 115.64, 114.18 (d, J = 11.0 Hz),113.66, 101.62, 101.13, 72.50, 67.74, 66.79, 61.47 (d, J =12.5 Hz), 55.66, 54.09 (d, J = 14.2 Hz), 50.39.]]> D14 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.48 (m, 3H), 7.33 – 7.30 (m, 2H), 7.17 (s, 1H),7.09 (d, J = 8.9 Hz, 1H), 6.99 (d, J = 8.5 Hz, 2H), 6.85 (t, J = 9.2 Hz, 1H), 6.42 (d, J = 3.1 Hz, 1H), 4.95 (dd, J =40.5, 4.4 Hz, 2H), 4.21 (dd, J = 14.3, 3.6 Hz, 1H), 4.15 (d, J = 7.1 Hz, 1H), 4.08 – 3.99 (m, 3H), 3.96 – 3.91 (m, 1H),3.79 (s, 3H), 2.51 – 2.44 (m, 6H), 2.44 – 2.29 (m, 4H), 2.22– 2.15 (m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.74,160.12, 159.51, 158.26, 157.93, 154.01, 136.94 (d, J = 12.7Hz), 130.91, 130.61, 127.47, 125.08, 124.59, 123.87, 121.59(d, J = 10.4 Hz), 118.04, 115.64, 114.13, 107.76, 107.56,101.62, 101.03, 97.23, 97.02, 72.50, 67.72, 66.80, 61.56 (d, J = 36.8 Hz), 55.66, 54.07 (d, J = 9.8 Hz), 50.59. 19 F NMR(471 MHz, DMSO- D 6) d -121.94.<!-- 14 --> ]]> D15 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.54 (s, 1H), 8.41 (s, 1H), 8.02(d, J = 8.9 Hz, 1H), 7.89 (dd, J = 8.8, 2.1 Hz, 1H), 7.75 –7.70 (m, 2H), 7.54 – 7.51 (m, 2H), 7.16 (d, J = 2.4 Hz, 1H),7.09 (dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m, 2H), 6.65(dd, J = 3.0, 0.8 Hz, 1H), 5.03 (dd, J = 28.6, 4.6 Hz, 2H),4.39 (dt, J = 14.3, 2.9 Hz, 1H), 4.31 – 4.25 (m, 1H), 4.15(dd, J = 9.7, 2.9 Hz, 1H), 4.05 – 3.97 (m, 3H), 3.78 (s, 3H),2.51 – 2.43 (m, 6H), 2.43 – 2.24 (m, 4H), 2.22 – 2.13 (m,2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.15, 163.75, 159.51,157.92, 154.00, 142.27, 136.95, 135.57, 133.36, 130.61,127.46, 124.59, 123.87, 120.94, 118.04, 115.63, 114.45,114.13, 108.26, 102.17, 101.62, 72.50, 67.65 (d, J = 4.8 Hz),66.81, 61.44, 55.66, 54.05, 50.71.]]> D16 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 2H), 7.49 – 7.46 (m, 1H), 7.44 (d, J =3.2 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.12 – 7.06 (m, 3H),7.01 – 6.98 (m, 2H), 6.45 (dd, J = 3.1, 0.8 Hz, 1H), 4.96(dd, J = 29.4, 4.6 Hz, 2H), 4.29 (dd, J = 14.3, 3.6 Hz, 1H),4.16 – 4.08 (m, 2H), 4.04 – 3.93 (m, 3H), 3.79 (s, 3H), 2.50– 2.43 (m, 6H), 2.39 (dd, J = 12.6, 5.6 Hz, 4H), 2.24 – 2.17(m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.75, 159.51,157.93, 154.01, 137.71, 131.36, 130.61, 127.48, 126.79,124.79, 124.59, 123.88, 122.08, 118.88, 118.05, 115.64,114.13, 110.03, 101.62, 98.94, 72.50, 67.62, 66.80, 61.86,61.40, 55.67, 54.07 (d, J = 9.5 Hz), 50.91.]]> D17 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 3H), 7.45 (d, J = 3.2 Hz, 1H), 7.22 (dd, J = 7.6, 0.7 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.09 (dd, J =8.9, 2.4 Hz, 1H), 7.05 (dd, J = 8.2, 7.6 Hz, 1H), 7.01 – 6.98(m, 2H), 6.38 (dd, J = 3.1, 0.8 Hz, 1H), 4.96 (dd, J = 29.5,4.7 Hz, 2H), 4.28 (dd, J = 14.3, 3.6 Hz, 1H), 4.15 – 4.07 (m,2H), 4.04 – 3.99 (m, 2H), 3.96 – 3.92 (m, 1H), 3.79 (s, 3H),2.50 – 2.42 (m, 6H), 2.42 – 2.32 (m, 4H), 2.23 – 2.19 (m,2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.75, 159.51,157.93, 154.01, 137.31, 131.34, 130.61, 128.69, 127.48,124.59, 123.87, 122.44, 121.98, 118.04, 115.64, 114.13,113.93, 110.49, 101.62, 100.62, 72.51, 67.62, 66.80, 61.87,61.41, 55.67, 54.08 (d, J = 9.1 Hz), 50.95. <!-- 15 -->]]> D18 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 2H), 7.37 (d, J = 3.2 Hz, 1H), 7.32 (dd, J = 8.3, 0.9 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.10 – 7.06(m, 2H), 7.01 – 6.98 (m, 2H), 6.79 – 6.75 (m, 1H), 6.47 (dd, J = 3.2, 0.8 Hz, 1H), 4.96 (dd, J = 30.5, 4.6 Hz, 2H), 4.28(dd, J = 14.3, 3.6 Hz, 1H), 4.16 – 4.13 (m, 1H), 4.09 (dd, J = 14.3, 6.6 Hz, 1H), 4.05 – 3.99 (m, 2H), 3.97 – 3.92 (m,1H), 3.79 (s, 3H), 2.50 – 2.43 (m, 6H), 2.43 – 2.30 (m, 4H),2.24 – 2.20 (m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16,163.74, 159.51, 157.93, 156.98, 155.04, 154.01, 139.61 (d, J = 11.7 Hz), 130.64 (d, J = 7.3 Hz), 127.47, 124.59, 123.87,121.78 (d, J = 7.4 Hz), 118.04, 117.11, 116.93, 115.63,114.13, 107.38, 103.90 (d, J = 18.6 Hz), 101.62, 96.39,72.50, 67.61, 66.79, 61.92, 61.40, 55.66, 54.08 (d, J = 9.9Hz), 50.92. 19 F NMR (471 MHz, DMSO- D 6) δ -122.85.]]> D19 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.51 (m, 2H), 7.20 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.10 – 7.05 (m, 2H), 7.04 – 6.99 (m, 3H),6.50 (dd, J = 7.6, 1.0 Hz, 1H), 6.40 (dd, J = 3.2, 0.7 Hz,1H), 5.03 – 4.86 (m, 2H), 4.23 (dd, J = 14.3, 3.8 Hz, 1H),4.16 – 4.13 (m, 1H), 4.05 – 3.99 (m, 3H), 3.93 (s, 1H), 3.85(s, 3H), 3.79 (s, 3H), 2.50 – 2.44 (m, 6H), 2.43 – 2.31 (m,4H), 2.22 (d, J = 6.3 Hz, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ175.16, 163.74, 159.51, 157.93, 154.02, 153.23, 138.11,130.61, 128.55, 127.48, 124.59, 123.87, 122.19, 118.78,118.04, 115.64, 114.13, 104.02, 101.62, 99.45, 97.99, 72.49,67.71, 66.77, 61.96, 61.38, 55.66, 55.40, 54.07 (d, J = 10.6Hz), 50.78, 11.80. <!-- 16 -->]]> D20 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (s, 1H), 8.03 (d, J = 8.9 Hz,1H), 7.54 – 7.52 (m, 2H), 7.30 – 7.27 (m, 2H), 7.17 (d, J =2.4 Hz, 1H), 7.09 (dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m,3H), 6.80 – 6.78 (m, 1H), 6.42 (dd, J = 3.1, 0.8 Hz, 1H),4.93 (dd, J = 56.7, 4.7 Hz, 2H), 4.25 (dd, J = 14.3, 3.8 Hz,1H), 4.16 – 4.13 (m, 1H), 4.06 – 4.00 (m, 3H), 3.95 – 3.91(m, 1H), 3.79 (s, 3H), 2.50 – 2.45 (m, 5H), 2.45 (s, 4H),2.43 – 2.33 (m, 4H), 2.22 (d, J = 6.3 Hz, 2H). 13 C NMR (126MHz, DMSO- D 6) δ 175.16, 163.75, 159.51, 157.93, 154.01,136.43, 130.62, 129.48 (d, J = 3.8 Hz), 128.38, 127.48,124.59, 123.88, 121.36, 119.41, 118.04, 115.64, 114.13,108.21, 101.62, 99.26, 72.51, 67.74, 66.79, 62.00, 61.41,55.66, 54.10 (d, J = 9.7 Hz), 50.71, 19.00.]]> D21 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.41 (d, J = 0.8 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.39 (d, J = 8.0 Hz,1H), 7.26 (s, 1H), 7.22 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4Hz, 1H), 7.09 (dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m, 2H),6.82 (dd, J = 8.1, 1.4 Hz, 1H), 6.33 (dd, J = 3.1, 0.8 Hz,1H), 4.95 (dd, J = 52.9, 4.5 Hz, 2H), 4.24 – 4.19 (m, 1H),4.17 – 4.12 (m, 1H), 4.05 – 3.99 (m, 3H), 3.94 – 3.89 (m,1H), 3.78 (s, 3H), 2.50 – 2.41 (m, 7H), 2.40 (s, 4H), 2.39 –2.26 (m, 2H), 2.21 (d, J = 6.3 Hz, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.74, 159.51, 157.93, 154.01, 137.17, 130.61,130.20, 129.54, 127.47, 126.32, 124.59, 123.87, 120.99,120.43, 118.04, 115.64, 114.13, 110.40, 101.61, 100.51,72.50, 67.78, 66.79, 61.87, 61.43, 55.66, 54.12 (d, J = 11.3Hz), 50.36, 22.16. <!-- 17 -->]]> D22 <![CDATA[ 1 H NMR (500 MHz, DMSO- D 6) δ 8.42 (d, J = 0.9 Hz, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.54 – 7.51 (m, 2H), 7.35 – 7.33 (m, 1H),7.25 (d, J = 3.1 Hz, 1H), 7.17 (d, J = 2.4 Hz, 1H), 7.09 (dd, J = 8.9, 2.4 Hz, 1H), 7.01 – 6.98 (m, 2H), 6.87 – 6.80 (m,2H), 6.36 (d, J = 3.1 Hz, 1H), 4.93 (dd, J = 56.3, 4.8 Hz,2H), 4.62 – 4.54 (m, 1H), 4.16 – 4.09 (m, 2H), 4.05 – 3.98(m, 2H), 3.86 – 3.81 (m, 1H), 3.79 (s, 3H), 2.69 (s, 3H),2.50 – 2.42 (m, 7H), 2.37 (dd, J = 12.7, 5.9 Hz, 3H), 2.30 –2.24 (m, 2H). 13 C NMR (126 MHz, DMSO- D 6) δ 175.16, 163.75,159.51, 157.93, 154.01, 134.97, 131.53, 130.61, 129.69,127.48, 124.59, 124.42, 123.88, 121.24, 119.37, 119.01,118.04, 115.64, 114.13, 101.62, 100.98, 72.50, 69.15, 66.79,62.65, 61.41, 55.66, 54.18 (d, J = 16.6 Hz), 53.05, 20.57.]]> Experimental Example 1 Anti-plant pathogenic fungal activity test Test method: Nine plant fungi (Actinidia kiwifruit) were studied using the mycelial growth rate method. Ps Phytophthora capsici, Pc Anthracnose in chili peppers, Cg Rice sheath blight pathogen, Rs Fusarium head blight, FgBlack spot disease of Chinese cabbage, Ab Cucumber wilt pathogen, Foc Fusarium wilt of peppers, Fo Sclerotinia sclerotiorum, Ss In vitro activity evaluation was performed, using the commercial drug azoxystrobin as a positive control, and the compound was measured at 100... µ Antibacterial activity at a concentration of g / mL.

[0062] The specific steps are as follows: Preparation of PDA medium: Weigh 40 g potato dextrose agar powder, add an appropriate amount of deionized water, heat to boiling and dilute to 1000 mL. Then dispense the medium into 50 mL Erlenmeyer flasks (measure 20 mL using a 50 mL graduated cylinder), seal the Erlenmeyer flasks with sealing film and rubber bands, and autoclave at 121 °C for 20 min for later use.

[0063] Drug preparation: Weigh 2 mg of the drug and add 200 ml of water. µ Dissolve in L DMSO and set aside for later use.

[0064] Activation of the bacterial strain: Under aseptic conditions, the surface of the sterilized PDA medium was disinfected with 75% ethanol and transferred to a laminar flow hood. After the medium cooled to a suitable temperature (approximately 50°C), it was evenly poured into 90 mm sterile Petri dishes. Once the agar had completely solidified, a 5 mm sterile punch was used to obtain a bacterial agar block, which was then precisely inoculated into the center of the medium using an inoculation needle. After inoculation, the edges of the Petri dishes were sealed with sealing film and placed in a 28±1°C incubator for dark incubation. Once the colonies had expanded to the edge of the Petri dish, it was ready for subsequent antibacterial activity assays.

[0065] Antifungal activity test: 30 minutes before the experiment, prepare the required culture dishes (60 mm) and 200 ml of water. µ L-type pipette, 5 mm punch, sterile syringe, prepared medication solution, 200 µ Place the L-tip into the laminar flow hood and sterilize with UV light; after 30 minutes, light the alcohol lamp and number the culture dishes inside the laminar flow hood; place the autoclaved PDA culture medium into the laminar flow hood, and use a pipette to aspirate 200 ml of the medium inside the laminar flow hood. μ L of the drug solution (DMSO as a blank control, azoxystrobin as a positive control) was added to 20 mL of sterilized PDA medium and mixed thoroughly to prepare a compound concentration of 100%. μDispense the culture medium at a concentration of g / mL evenly into three 60 mm sterile Petri dishes and allow it to solidify. In a laminar flow hood, use a 5 mm punch to create 5 mm diameter mycelial discs from the activated fungal culture. Inoculate these discs with the mycelium facing down in the center of the culture medium using an inoculation needle. Seal the Petri dishes with sealing film. Then, place them in a 28 ℃ incubator and invert them for incubation. When the mycelial diameter on the surface of the blank group reaches 4.5-5.0 cm, measure the mycelial diameter of each group using the cross-sectional method and record the data. Calculate the inhibition rate using the following formula: I(%) = (CT) / (C - 5 mm) × 100% I: Inhibition rate; C: Diameter of hyphae growth in the blank control group; T: Diameter of mycelial growth in the compound-treated group. The results of the bioactivity test against plant pathogenic fungi are shown in Table 3.

[0066] Table 3. In vitro antifungal activity of D1-D22 (100 μL / mL) μ g / mL) Compounds D1 93.3±1.3 80.4±0.9 80.7±2.6 84.1±0.0 67.0±1.6 75.9±0.9 63.3±1.2 78.5±1.1 65.2±2.0 D2 90.8±1.0 84.1±0.0 77.3±1.1 85.0±1.2 51.2±1.2 71.9±1.1 28.3±0.9 71.0±1.7 66.8±1.2 D3 91.8±1.2 85.0±1.2 83.9±1.6 71.8±1.9 49.6±1.6 72.2±1.2 44.2±1.2 71.9±0.9 71.3±1.1 D4 87.7±0.0 71.8±1.9 65.9±1.2 80.2±1.3 50.0±1.9 71.1±0.0 36.1±0.9 68.4±1.7 70.9±2.6 D5 92.5±1.0 80.2±1.3 85.9±1.8 50.2±1.8 71.0±0.9 74.8±1.1 38.2±1.2 74.5±1.7 76.6±1.2 D6 52.6±1.4 50.2±1.8 23.5±1.2 86.3±1.0 20.6±1.7 53.3±1.4 17.6±1.4 38.5±1.9 43.0±2.2 D7 92.8±1.0 86.3±1.0 90.2±0.9 63.0±1.5 64.7±2.8 76.7±1.9 45.1±1.9 69.3±1.7 75.8±1.6 D8 60.1±2.3 63.0±1.5 38.4±1.6 83.3±1.2 12.7±1.7 36.7±1.2 12.0±1.7 40.3±1.5 51.6±1.1 D9 90.4±1.5 83.3±1.2 76.5±1.3 64.3±1.3 56.0±1.2 69.3±2.2 34.8±1.2 68.8±2.9 72.5±0.9 D10 89.4±0.8 67.4±2.8 64.3±2.8 84.1±0.0 58.3±1.2 70.7±0.9 44.6±1.2 64.1±2.7 72.1±1.1 D11 90.0±1.1 85.2±1.2 90.7±0.9 68.9±2.3 72.2±1.2 78.9±1.2 69.3±0.9 78.9±1.2 64.4±1.7 D12 88.9±1.3 84.8±0.9 86.3±1.6 72.2±1.1 68.5±0.9 76.7±1.2 45.6±1.9 73.0±1.6 67.8±2.0 D13 87.0±1.6 84.8±0.9 66.3±2.1 57.0±1.7 61.5±1.1 74.4±1.2 51.9±1.1 70.7±0.9 63.0±2.0 D14 92.6±1.1 84.1±0.9 86.3±0.9 81.1±2.2 69.6±1.1 80.0±1.4 63.3±1.2 79.3±1.1 63.3±1.0 D15 60.4±2.0 73.7±0.9 41.5±1.1 46.7±1.3 51.5±1.6 60.7±1.1 43.0±1.1 63.7±1.7 53.0±1.9 D16 92.6±1.1 83.3±1.2 87.8±1.2 85.6±2.2 64.4±1.4 79.6±0.9 51.1±0.0 80.4±1.6 57.4±1.4 D17 91.5±0.8 83.7±1.2 81.1±1.2 73.3±1.8 58.5±1.1 78.1±0.9 57.0±2.3 75.2±1.6 61.5±1.6 D18 93.7±0.8 88.5±0.9 90.0±1.2 70.7±0.8 73.0±1.6 79.6±0.9 69.6±1.1 82.6±0.9 58.9±1.0 D19 88.9±1.3 78.1±0.9 71.1±1.9 67.4±1.1 65.6±1.8 75.9±0.9 57.0±1.1 77.0±1.1 57.4±1.9 D20 95.2±0.8 87.4±1.2 89.3±0.9 71.1±0.0 78.9±1.2 79.3±1.1 69.6±1.1 82.6±0.9 70.4±1.6 D21 91.9±1.1 87.8±1.2 91.9±1.1 73.7±1.6 74.1±1.1 78.1±0.9 66.3±0.9 76.3±2.2 60.0±0.0 D22 90.0±1.1 88.5±0.9 84.4±1.4 50.0±1.1 64.8±1.6 76.7±1.2 61.1±1.2 75.9±2.1 56.3±1.0 FMN 6.2±1.3 31.9±1.1 15.9±0.9 42.6±0.7 - 13.7±0.9 25.2±1.1 30.0±1.2 11.9±1.1 Az 73.0±2.0 59.3±1.2 69.6±1.1 78.9±1.1 52.6±2.7 77.4±0.9 53.3±1.4 51.5±1.6 73.4±0.9 As can be seen from Table 3, all target compounds are at 100 μ At a concentration of g / mL, all compounds exhibited inhibitory activity against nine plant fungi. Among them, compounds D1-D3, D5, D7, D9, D11, D14, D16-D18, and D20-D22 showed inhibitory activity against [various fungal species]. Ps The inhibition rates of all compounds were above 90%, superior to azoxystrobin (70.3%). Compounds D3, D7, D11, D18, and D20-D22 showed inhibitory effects on... Pc The inhibitory activity of all compounds was above 85%, superior to that of azoxystrobin (59.3%). Compounds D7, D11, D12, D14, D16, D18, D20, and D21 showed inhibitory activity against [various pathogens / organizations]. Cg The inhibition rates of all compounds were above 85%, with D7, D11, D18, and D21 showing inhibition rates above 90%, superior to azoxystrobin (69.6%). Furthermore, some compounds showed inhibition rates against six other plant pathogens (…). Rs , Fg , Ab , Foc , Fo , Ss) It also exhibits good antibacterial activity. Overall, the target compound... Ps The inhibitory activity of the target compound is significantly better than that of other plant pathogens. Therefore, the target compound has specific inhibitory activity against Actinidia kiwifruit.

[0067] The above experimental activity data show that the indole-containing styracin derivative has a good inhibitory effect on plant pathogenic fungi, especially Actinidia kiwifruit, and can be used as a potential anti-plant pathogen drug with good application prospects.

[0068] The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

Claims

1. A genistein derivative containing indole, characterized in that, The structure is shown in the following formula: ； In the above formula, R is independently selected from H, one or more halogens, one or more nitro groups, one or more C1-C6 alkyl groups or C1-C6 alkoxy groups.

2. A method for preparing the indole-containing strychnosine derivative of claim 1, characterized in that the step... include: (1) Using indole and epoxybromopropane as raw materials and sodium hydride as catalyst, the reaction is carried out under reflux in a solvent. After the reaction is completed, the mixture is extracted with dichloromethane and the extract is evaporated to dryness to obtain intermediate a. The structural formula of the epoxybromopropane is: ; The structural formula of intermediate a is: ; (2) Using gentianin and epoxybromopropane as raw materials and anhydrous potassium carbonate as catalyst, the reaction was carried out at room temperature. After the reaction was completed, ice water was added to precipitate the product. The product was filtered, and the residue was cleaned of impurities to obtain intermediate b. The structural formula of intermediate b is: ; (3) Using intermediate b and piperazine as raw materials and anhydrous potassium carbonate as catalyst, the reaction was carried out in a solvent under reflux. After the reaction was completed, ice water was added to precipitate the product. The product was filtered, and the residue was cleaned to obtain intermediate c. The structural formula of the intermediate c is: ; (4) Using intermediates c and a as raw materials and anhydrous potassium carbonate as catalyst, the mixture is heated under reflux in a solvent. After the reaction is complete, ice water is added to precipitate the product. The product is filtered, and the residue is cleaned of impurities to obtain the indole-containing gentianin derivative.

3. The preparation method according to claim 2, characterized in that, In step (1), the molar ratio of indole, epoxybromopropane, and sodium hydride is 12.8:25.6:25.6; the heating temperature is 80℃; the reaction time is 2-5h; and the solvent is N,N-dimethylformamide.

4. The preparation method according to claim 2, characterized in that, In step (2), the molar ratio of styracidium, epoxybromopropane, and anhydrous potassium carbonate is 18.6:37.3:55.9; the reaction time is 1 day; the solvent is N,N-dimethylformamide; the impurity removal step includes: washing the filter residue sequentially with water and petroleum ether, then allowing it to stand and filter to complete the washing.

5. The preparation method according to claim 2, characterized in that, In step (3), the molar ratio of intermediate b, piperazine, and anhydrous potassium carbonate is 6.2:20.4:18.5; the reaction temperature is 80℃; the reaction time is 2-4h; the solvent is isopropanol; the impurity removal step includes: washing the filter residue sequentially with water and petroleum ether, then allowing it to stand and filter to complete the washing.

6. The preparation method according to claim 2, characterized in that, In step (4), the molar ratio of intermediate c, intermediate a and anhydrous potassium carbonate is 2.44:4.4:7.3; the heating reaction temperature is 80℃; the reaction time is 2-4h; the solvent is isopropanol; the impurity removal step includes: washing the filter residue with water and petroleum ether in sequence, then letting it stand and filtering to complete the washing.

7. The use of an indole-containing strychnosine derivative as described in claim 1 in the preparation of a drug for inhibiting plant pathogenic fungi.

8. The application according to claim 7, characterized in that, The plant pathogenic fungi include *Actinidia kiwifruit* (Ps); *Phytophthora capsici* (Pc); and *Anthracnose capsici* (Cg). Rice sheath blight pathogen, Rs; wheat scab pathogen, Fg; Chinese cabbage black spot pathogen, Ab; cucumber wilt pathogen, Foc; pepper wilt pathogen, Fo; Sclerotinia sclerotiorum, the causal agent of rapeseed disease.

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