Alpha-aryl selenide compound, synthesis method and application thereof

Abstract

This invention belongs to the fields of organic chemical synthesis technology and pharmaceutical synthesis technology, specifically relating to an α-arylselenium compound, its synthesis method, and its application. The preparation method includes the following steps: 1) using sulfone-thioylide compound and selenophenol as raw materials, adding them to a solvent, and stirring at 10-30℃ to obtain a reaction solution; 2) reacting the reaction solution at 10-30℃ to obtain the α-arylselenium compound.

Description

Technical Field

[0001] This invention belongs to the fields of organic chemical synthesis technology and drug synthesis technology, specifically relating to an α-arylselenium compound, its synthesis method and application. Background Technology

[0002] Organoselenium compounds have extremely wide applications in numerous fields such as pesticides, pharmaceuticals, and materials. In the pharmaceutical field, the introduction of selenium atoms can significantly enhance drug activity; for example, the introduction of selenium into celecoxib derivatives enhances their antitumor activity; the introduction of diselenoside into camptothecin also significantly enhances its antitumor activity. Furthermore, α-carbonylselenoketones / esters can be further modified through various reactions, such as reduction to β-hydroxyselenolactone, which is an important synthetic intermediate for constructing natural products such as pancreatic kallikrein inhibitors. Therefore, the synthesis of organoselenium compounds, especially α-arylselenoketones / esters, is particularly important. Developing efficient and rapid methods for constructing C-Se bonds for the synthesis and modification of drug molecules is of great significance.

[0003] One of the most classic methods for synthesizing α-arylselenoketones is using haloselenophenols as the selenium source and α-haloketones as the α-arylselenoketone (Synth. Commun., 1996, 26, 8). Many other synthetic methods often involve the synthesis of α-arylselenoketones from alkenes, alkynes, and azides under the catalysis of transition metals with selenium ethers. The extensive use of transition metals is not only costly but also causes environmental pollution. Ling Yong's research group proposed a method for synthesizing α-arylselenoketones using diselenoethers as the selenium source through a photocatalytic oxidative coupling reaction with alkenes, avoiding the problems associated with transition metals. However, the photocatalytic method is not conducive to industrial scale-up, affecting its practicality. Summary of the Invention

[0004] To address the shortcomings of existing technologies, this invention provides an α-arylselenium compound, its synthesis method, and its applications. The method provided by this invention features simple steps, mild conditions, readily available and simple raw materials, rapid reaction speed, a wide range of applicable substrates, and a yield as high as 95%. It also exhibits good reaction selectivity, offering certain advantages for industrial production. The α-arylselenium compound provided by this invention demonstrates excellent activity against Candida albicans and Cryptococcus neoformans.

[0005] The technical solution provided by this invention is as follows: An α-arylselenium compound, wherein the α-arylselenium compound is an α-arylselenoketone or an α-arylselenoester, and the structural formula of the α-arylselenoketone is as follows: The structural formula of the α-aryl selenide is as follows: ; in: R5 is an aryl or heteroaryl, straight-chain or branched alkane, cycloalkane, steroidal or disubstituted amino group; R6 is an aryl or heteroaryl, straight-chain or branched alkane or cycloalkane group; R7 is an aryl or heteroaryl, straight-chain or branched alkane, cycloalkane, steroidal or disubstituted amino group; R8 is an aryl or heteroaryl, straight-chain or branched alkane, cycloalkane, or disubstituted amino group.

[0006] The aforementioned α-aryl selenium compounds, as organoselenium compounds, have advantages such as antidepressant and anti-inflammatory properties, and also have anti-Candida albicans or Cryptococcus neoformans activity.

[0007] The aforementioned aryl or heteroaryl, straight-chain or branched alkane, cycloalkane or disubstituted amino groups may be substituted or unsubstituted, respectively.

[0008] Preferably, the aryl group is phenyl or naphthyl, and the aryl group is substituted by one or more identical or different groups, wherein the groups are selected from halogens, C4-C6 straight-chain and branched alkyl groups, C3-C6 cycloalkyl groups, hydroxyl groups, amino groups, carboxyl groups, amino groups, C1-C6 straight-chain and branched alkoxy groups, C1-C6 straight-chain and branched perhaloalkyl groups, C1-C6 straight-chain and branched alkyl groups substituted with one or more halogens, C1-C6 straight-chain and branched alkyl groups substituted with one or more hydroxyl groups, C2-C6 straight-chain and branched alkylthio groups, straight-chain and branched perhaloalkyl groups, alkoxy groups, nitro groups, cyano groups, ester groups, amide groups, amino groups, oxycarbonyl groups, or C1-C6 carboxylic acids; Preferably, the heteroaromatic compounds refer to furanyl, pyrimidinyl, pyridinyl, thiazolyl, oxazolyl, isoxazolyl, indolyl, porphyrinyl, quinolinyl, isoquinolinyl, pyranyl, or pyridazinyl. Preferably, the straight-chain or branched alkane group is a C1-C6 straight-chain or branched alkane group; Preferably, the cycloalkane group is a C3-C6 cycloalkane group; Preferably, the disubstituted amino group is a C1-C3 dialkyl or diphenyl substituted group.

[0009] This invention also provides a method for preparing α-arylselenium compounds, comprising the following steps: 1) Using sulfone-based sulfur ylide compounds and benzeneselenophenol as raw materials, add them to a solvent and stir at 10-30℃ (preferably 20℃) to obtain a reaction solution; 2) The reaction solution is reacted at 10-30℃ (preferably 20℃) to obtain α-arylselenium compounds.

[0010] The above preparation method can synthesize α-arylselenylmethyl ketones or esters without the need for catalyst catalysis. The steps are simple and the conditions are mild.

[0011] Specifically, the sulfone-thio ylide compound is an α-carbonyl thio ylide or a phenyl thio ylide carboxylic acid ester; The structural formula of the α-carbonyl thioylide is shown in Formula 1 below: The structural formula of the phenylthioyl ylide carboxylate is shown in Formula 2 below: The structural formula of the selenophenol is shown in Formula 3 below: R1 is an aryl or heteroaryl, straight-chain or branched alkane, cycloalkane, steroidal or disubstituted amino group; R2 is aryl; R3 is an aryl or heteroaryl group.

[0012] The aforementioned aryl or heteroaryl, straight-chain or branched alkane, cycloalkane or disubstituted amino groups may be substituted or unsubstituted, respectively.

[0013] Preferably, the aryl group is phenyl or naphthyl, and the aryl group is substituted by one or more identical or different groups, wherein the groups are selected from halogens, C4-C6 straight-chain and branched alkyl groups, C3-C6 cycloalkyl groups, hydroxyl groups, amino groups, carboxyl groups, amino groups, C1-C6 straight-chain and branched alkoxy groups, C1-C6 straight-chain and branched perhaloalkyl groups, C1-C6 straight-chain and branched alkyl groups substituted with one or more halogens, C1-C6 straight-chain and branched alkyl groups substituted with one or more hydroxyl groups, C2-C6 straight-chain and branched alkylthio groups, straight-chain and branched perhaloalkyl groups, alkoxy groups, nitro groups, cyano groups, ester groups, amide groups, amino groups, oxycarbonyl groups, or C1-C6 carboxylic acids; Preferably, the heteroaryl group is furanyl, pyrimidinyl, pyridinyl, thiazolyl, oxazolyl, isoxazolyl, indolyl, porphyrinyl, quinolinyl, isoquinolinyl, pyranyl, or pyridazinyl; Preferably, the straight-chain or branched alkane group is a C1-C6 straight-chain or branched alkane group; Preferably, the cycloalkane group is a C3-C6 cycloalkane group; Preferably, the disubstituted amino group is a C1-C3 dialkyl or diphenyl substituted group.

[0014] More preferably, R1 is selected from phenyl, 4-MeC6H4, 4-FC6H4, 4-BrC6H4, 4-IC6H4, 4-NO2C6H4, 4- tBuC6H4, 3-MeOC6H4, 3-BrSC6H4, 2-IC6H4, N(Et)2, N(Ph)2, 5-ClBu, Bu, Bn, CyBu, 2-furanyl, 3,5-bis(trifluoromethylphenyl), 17-oxosteroidyl, 3,7,12-trioxosteroidyl, 3-thienyl, 2-thienyl, 2-naphthyl; More preferably, R2 is selected from H, 4-Me, 4-NO2, 4-Br, 4-F, 4-Cl, 4-CN, and 3,5-bis(trifluoromethyl)-substituted aryl groups; More preferably, R3 is selected from H, methyl, ethyl, phenyl, trifluoromethyl, Cl, F, 3-furanyl, 3-thienyl, 2-furanyl, 2-thienyl, benzyl, cyclohexyl, n-butyl, methyl, N(Et)2, N(Ph)2 substituted aryl groups.

[0015] Specifically, in step 1): The molar ratio of the sulfone-thioylide compound to the selenophenol is 1.4-1.6:1; The solvent is one or more selected from ethyl acetate, acetonitrile, 1,4-dioxane, methanol, tetrahydrofuran, toluene, dichloromethane, 1,2-dichloroethane, N,N-dimethylformamide, or methyl tert-butyl ether. The total concentration of the raw materials in the reaction solution is 0.24-0.26 mol / L.

[0016] Specifically, in step 2): the reaction temperature is 22-28℃ and the reaction time is 5-180 min.

[0017] Specifically, the general reaction formula is as follows: Furthermore, step 3) involves evaporating the reaction solution under reduced pressure to dryness, and purifying the residue by column chromatography to obtain α-arylselenoketone or α-arylselenoester; the eluent used in the column chromatography purification is a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:25-35.

[0018] The above purification method yields α-arylselenophenones and α-arylselenoesters with yields as high as 95%. This invention also provides applications of α-arylseleno compounds for the preparation of antifungal drugs.

[0019] Preferably, the solvent is DCM.

[0020] Preferably, the molar ratio of the sulfone-thioylide compound and selenophenol is 1.5:1.

[0021] Preferably, the concentration of the reaction solution is 0.25 mol / L.

[0022] Preferably, the reaction temperature is 25℃ and the reaction time is 5 to 180 min.

[0023] Preferably, after the reaction is completed, the reaction solution is evaporated to dryness under reduced pressure, and the residue is purified by column chromatography. The eluent used in the column chromatography purification is a mixture of ethyl acetate and petroleum ether at a volume ratio of 1:30.

[0024] Specifically, drugs for the preparation of anti-Candida albicans (BNCC186382) or anti-Cryptococcus neoformans (BNCC245768).

[0025] For Candida albicans, the antibacterial effect can reach a minimum inhibitory concentration (MIC) of less than 1 μg / mL.

[0026] For Cryptococcus neoformans, the antibacterial effect can reach a minimum inhibitory concentration (MIC) of less than 1 μg / mL.

[0027] Compared with the prior art, the beneficial effects of the present invention include: This invention provides a safe and efficient method for synthesizing α-arylselenyl methyl ketones / esters without the need for catalyst catalysis. The method is simple, operates under mild conditions, uses readily available raw materials, and has a fast reaction rate. It has a wide range of applicable substrates, achieves a yield of up to 95%, and exhibits good reaction selectivity, offering advantages for industrial production. Furthermore, the α-arylselenium compounds demonstrate excellent activity against Candida albicans and Cryptococcus neoformans, providing new ideas and frameworks for the development of antifungal drugs. Attached Figure Description

[0028] Figure 1 3a obtained in Example 1 1 1H-NMR (H-NMR spectrum).

[0029] Figure 2 3a obtained in Example 1 13 C-NMR (carbon nuclear magnetic resonance).

[0030] Figure 3 The 3ba obtained in Example 5 1 1H-NMR (H-NMR spectrum).

[0031] Figure 4 The 3ba obtained in Example 5 13 C-NMR (carbon nuclear magnetic resonance).

[0032] Figure 5 5a obtained in Example 6 1 1H-NMR (H-NMR spectrum).

[0033] Figure 65a obtained in Example 6 13 C-NMR (carbon nuclear magnetic resonance). Detailed Implementation

[0034] The principles and features of the present invention are described below. The embodiments given are only for explaining the present invention and are not intended to limit the scope of the present invention.

[0035] Unless otherwise specified, the test methods used in the embodiments are conventional methods; unless otherwise specified, the materials and reagents used are commercially available.

[0036] Explanation of Abbreviations and Terms Me: Methyl; Et: Ethyl; i Pr: Isopropyl; t Bu: tert-butyl; Bn: benzyl; Ph: phenyl; EtOAc: ethyl acetate; PE: petroleum ether; CyBu: cyclopropyl.

[0037] Example 1 Add 1a (20.0 mg, 0.10 mmol) and 2a (16.0 mg, 0.10 mmol) to the reaction tube, followed by 1 mL of dichloromethane as a solvent. Start the stirrer and react at 25 °C for 5 min. Evaporate the reaction mixture to dryness under reduced pressure. Purify the residue by column chromatography (silica gel, eluent: EtOAc / PE = 1:30) to obtain a yellow oily liquid (20.0 mg, yield: 71%). The 1H NMR spectrum of product 3a is shown below. Figure 1 As shown, the carbon NMR spectrum is as follows: Figure 2 As shown.

[0038] 1 H NMR (400 MHz, CDCl3) δ 7.91 – 7.85 (m, 2H), 7.59 – 7.51 (m, 3H), 7.43 (t, J = 7.7 Hz, 2H), 7.33 – 7.26 (m, 3H), 4.18 (s, 2H); 13 C NMR (100 MHz, CDCl3) δ 193.9, 134.5, 133.0, 132.2, 128.2, 128.1, 127.7, 127.6, 127.1, 31.7. This indicates that the compound with the structure shown in 3a above was successfully synthesized.

[0039] Example 2 Add 1a (20.0 mg, 0.10 mmol) and 2a (16.0 mg, 0.10 mmol) to the reaction tube, followed by 1 mL of dichloromethane as a solvent. Start the stirrer and react at 50 °C for 5 min. Evaporate the reaction mixture to dryness under reduced pressure. Purify the residue by column chromatography (silica gel, eluent: EtOAc / PE = 1:30) to obtain 19.0 mg of a yellow oily liquid (yield: 69%).

[0040] Example 3 Add 1a (20.0 mg, 0.10 mmol), 2a (16 mg, 0.10 mmol), and 1 mL of water as a solvent to the reaction tube. Start the stirrer and stir the reaction at 25 °C for 5 min. Product 3a was not obtained.

[0041] Example 4 Add 1a (29.0 mg, 0.15 mmol), 2a (16.0 mg, 0.10 mmol), and 1 mL of dichloromethane as solvent to the reaction tube. Start stirring and react at 25 °C for 5 min. Evaporate the reaction solution to dryness under reduced pressure, and purify the residue by column chromatography (silica gel, eluent: EtOAc / PE = 1:30) to obtain a yellow oily liquid (23.0 mg, yield: 82%).

[0042] Example 5 Add 1b (38.0 mg, 0.15 mmol) and 2a (16.0 mg, 0.10 mmol) to the reaction tube, followed by 1 mL of dichloromethane as a solvent. Start the stirrer and react at 25 °C for 5 min. Evaporate the reaction mixture to dryness under reduced pressure. Purify the residue by column chromatography (silica gel, eluent: EtOAc / PE = 1:30) to obtain a yellow oily liquid (31.4 mg, yield: 95%).

[0043] The 1H NMR spectrum of the obtained product 3ba is as follows: Figure 3 As shown, the carbon NMR spectrum is as follows: Figure 4 As shown. 1 H NMR (400 MHz, CDCl3) δ 7.82 (d, J = 8.6 Hz, 2H), 7.57 – 7.52 (m, 2H), 7.48 – 7.41 (m, 2H), 7.30 – 7.24 (m, 3H), 4.16 (s, 2H), 1.34 (s, 9H).13 C NMR (100 MHz, CDCl3) δ193.7, 156.1, 132.9, 131.8, 128.2, 128.2, 127.6, 126.9, 124.6, 34.1, 31.7,30.0.

[0044] Example 6 Add 4a (36.0 mg, 0.15 mmol), 2a (16.0 mg, 0.10 mmol), and 1 mL of dichloromethane as solvent to the reaction tube. Start stirring and react at 25 °C for 5 min. Evaporate the reaction solution to dryness under reduced pressure, and purify the residue by column chromatography (silica gel, eluent: EtOAc / PE = 1:30) to obtain a yellow oily liquid (25.0 mg, yield: 78%).

[0045] The 1H NMR spectrum of the obtained product 5a is as follows: Figure 5 As shown, the carbon NMR spectrum is as follows: Figure 6 As shown. 1 H NMR (400 MHz, CDCl3) δ 7.52 – 7.49 (m, 2H), 7.44 – 7.41 (m, 2H), 7.32 – 7.24 (m, 6H), 4.90 (s, 1H), 4.11 (q, J = 7.1 Hz, 2H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ 170.08, 135.23, 134.64, 127.95, 127.83, 127.65, 127.55, 127.46, 126.88, 60.49, 47.21, 12.94.

[0046] Comparative Example 1 The only difference from Example 1 is that the acid solvent is changed to water, methanol, DCE, EA, etc., while the other steps and conditions are the same as in Example 1. The reaction may not yield the target product or may reduce the yield.

[0047] As demonstrated in Example 1 and Comparative Example 1, different solvents can prevent this step of the reaction from proceeding. Therefore, DCM is the preferred solvent in the synthesis method of the present invention.

[0048] Comparative Example 2 The only difference from Example 1 was that the amount of α-carbonyl thioylide was adjusted to 39.0 mg (0.20 mmol), while the other steps and conditions were the same as in Example 1. The reaction yielded 16.5 mg of a white solid in 60% yield.

[0049] Comparative Example 3 The only difference from Example 1 was that the amount of selenophenol was adjusted to 17 mg (0.3 mmol), while the other steps and conditions were the same as in Example 1. The reaction did not yield the target product.

[0050] As observed in Examples 1, 2, and 3, an inappropriate molar ratio can result in a low yield for this step of the reaction. Therefore, the molar ratio of α-carbonylthioylide to selenophenol in the synthesis method of this invention is 1.5:1.

[0051] A method for synthesizing α-arylselenylmethyl ketones or esters involves adding α-carbonylthioylide and selenophenol to a solvent and reacting under stirring. This invention uses α-carbonylthioylide and selenophenol, which react at room temperature. After the reaction is complete, the product is purified by column chromatography to synthesize a series of α-arylselenylmethyl ketone / ester derivatives in high yields, ranging from 65% to 95%. The synthesis method of this invention is simple to operate, uses mild reaction conditions, readily available raw materials, has a wide range of applicable substrates, and achieves high yields.

[0052] Antibacterial test Standardized antifungal susceptibility testing was performed on *Candida albicans* (BNCC 186382) and *Cryptococcus neoformans* (BNCC 245768) according to CLSI guidelines. The test compound (2–5 mg) was accurately weighed and dissolved in analytical grade dimethyl sulfoxide (DMSO), with vortexing or heating as needed. Yeast mannitol broth (21.0 g / L) was prepared with reverse osmosis water and autoclaved. The final working concentrations of the target compounds were set at 128 μg / mL, 64 μg / mL, and 32 μg / mL, with the DMSO concentration controlled below 0.5‰. Fungal inoculum was prepared by adding 20 μL of *Candida albicans* or *Cryptococcus neoformans* stock solution to 2 mL of yeast mannitol broth and then incubating with shaking at 37°C for 24 hours.

[0053] For microdilution assays, 100 μL of sterile yeast mannitol broth was added to each well, followed by 4 μL of the test compound in the first column. A two-fold serial dilution was performed by transferring 100 μL of the solution. A standardized fungal suspension (prepared by adding 20 μL of inoculum to 20 mL of fresh yeast mannitol broth, 100 μL per well) was added to bring the final volume per well to 200 μL. The initial optical density (OD600) was recorded before incubation at 37°C for 24 hours. The percentage of inhibition relative to the growth control was calculated using the OD600 measurements after incubation.

[0054] The antibacterial effect of Candida albicans: minimum inhibitory concentration (MIC) less than 1 μg / mL.

[0055] Antibacterial experiment and efficacy of Cryptococcus neoformans: minimum inhibitory concentration (MIC) less than 1 μg / mL.

[0056] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. An α-arylselenium compound, wherein the α-arylselenium compound is an α-arylselenoketone or an α-arylselenium ester, characterized in that: The structural formula of the α-arylselenoketone is as follows: The structural formula of the α-aryl selenide is as follows: in: R5 is an aryl or heteroaryl, straight-chain or branched alkyl, cycloalkyl, steroidal or disubstituted amino group; R6 is aryl or heteroaryl, straight-chain or branched alkyl or cycloalkyl; R7 is an aryl or heteroaryl, straight-chain or branched alkyl, cycloalkyl, steroidal or disubstituted amino group; R8 is an aryl or heteroaryl, straight-chain or branched alkyl, cycloalkyl, or disubstituted amino group.

2. The α-arylselenium compound according to claim 1, characterized in that: The aryl group is phenyl or naphthyl, and the aryl group is either unsubstituted or substituted with one or more identical or different substituents. The substituents are selected from halogens, C4-C6 straight-chain and branched alkyl groups, C3-C6 cycloalkyl groups, hydroxyl groups, amino groups, amine groups, C1-C6 straight-chain and branched alkoxy groups, C1-C6 straight-chain and branched perhaloalkyl groups, C1-C6 straight-chain and branched alkyl groups substituted with one or more halogens, C1-C6 straight-chain and branched alkyl groups substituted with one or more hydroxyl groups, C2-C6 straight-chain and branched alkylthio groups, nitro groups, cyano groups, ester groups, amide groups, oxycarbonyl groups, or C1-C6 carboxyl groups. The heteroaryl group refers to furan, pyrimidine, pyridine, thiazole, oxazole, isoxazole, indole, porphyrin, quinoline, isoquinoline, pyran, or pyridazine; The straight-chain or branched alkyl group is a C1-C6 straight-chain or branched alkyl group; The cycloalkyl group is a C3-C6 cycloalkyl group; The disubstituted amino group is a C1-C3 dialkyl or diphenyl substituted group.

3. A method for producing an α-aryl selenide compound, characterized by, Includes the following steps: 1) Using sulfone-based sulfur ylide compounds and selenophenol as raw materials, add them to a solvent and stir at 10-30℃ to obtain a reaction solution; 2) The reaction solution was reacted at 10-30℃ to obtain α-arylselenium compounds.

4. The method for preparing the α-arylselenium compound according to claim 3, characterized in that: The sulfone-thio ylide compound is an α-carbonyl thio ylide or a phenyl thio ylide carboxylic acid ester. The structural formula of the α-carbonyl thioylide is shown in Formula 1 below: The structural formula of the phenylthioyl ylide carboxylate is shown in Formula 2 below: The structural formula of the selenophenol is shown in Formula 3 below: R1 is an aryl or heteroaryl, straight-chain or branched alkyl, cycloalkyl, steroidal or disubstituted amino group; R2 is aryl; R3 is an aryl or heteroaryl group.

5. The method for preparing the α-arylselenium compound according to claim 4, characterized in that: The aryl group is phenyl or naphthyl, and the aryl group is substituted by one or more identical or different groups, wherein the groups are selected from halogens, C4-C6 straight-chain and branched alkyl groups, C3-C6 cycloalkyl groups, hydroxyl groups, amino groups, amino groups, C1-C6 straight-chain and branched alkoxy groups, C1-C6 straight-chain and branched perhaloalkyl groups, C1-C6 straight-chain and branched alkyl groups substituted with one or more halogens, C1-C6 straight-chain and branched alkyl groups substituted with one or more hydroxyl groups, C2-C6 straight-chain and branched alkylthio groups, nitro groups, cyano groups, ester groups, amide groups, oxycarbonyl groups, or C1-C6 carboxylic acids; The heteroaryl group is furan, pyrimidine, pyridine, thiazole, oxazole, isoxazole, indole, porphyrin, quinoline, isoquinoline, pyran, or pyridazine; The straight-chain or branched alkyl group is a C1-C6 straight-chain or branched alkyl group; The cycloalkyl group is a C3-C6 cycloalkyl group; The disubstituted amino group is a C1-C3 dialkyl or diphenyl substituted group.

6. The method for preparing the α-arylselenium compound according to claim 3, characterized in that, In step 1): The molar ratio of the sulfone-thioylide compound to the selenophenol is 1.4-1.6:1; The solvent is one or more selected from ethyl acetate, acetonitrile, 1,4-dioxane, methanol, tetrahydrofuran, toluene, dichloromethane, 1,2-dichloroethane, N,N-dimethylformamide, or methyl tert-butyl ether. The total concentration of the raw materials in the reaction solution is 0.24-0.26 mol / L.

7. The method for preparing the α-arylselenium compound according to claim 3, characterized in that, In step 2): the reaction temperature is 22-28℃ and the reaction time is 5-180 min.

8. The method for preparing the α-arylselenium compound according to claim 3, characterized in that, It also includes step 3): the reaction solution is evaporated to dryness under reduced pressure, and the residue is purified by column chromatography to obtain α-arylselenoketone or α-arylselenoester; the eluent in the column chromatography purification is a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:25-35.

9. The application of an α-arylselenium compound according to claim 1 or 2, characterized in that: Used in the preparation of antifungal drugs.

10. An application according to claim 9, characterized in that: Used to prepare drugs against Candida albicans or Cryptococcus neoformans.

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