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Azole antifungal compound and its preparation method and application

A compound and antifungal technology, applied in antifungal agents, organic chemistry, pharmaceutical formulations, etc., can solve unseen problems, achieve good effect, high yield, and simple preparation method

Inactive Publication Date: 2015-04-08
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no azole compound 2-(2,4-difluorophenyl)-2-hydroxyl-3-(1 H Report on Propyl-1,2,4-triazol-1-yl)aminodithiocarbamate

Method used

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  • Azole antifungal compound and its preparation method and application
  • Azole antifungal compound and its preparation method and application
  • Azole antifungal compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 Preparation of the compound of the present invention

[0031] (1) Preparation of 2-(2,4-difluorophenyl)-2-hydroxyl-3-(1 H -1,2,4-triazol-1-yl)diethylaminodithiocarbamate (compound 1k in Table 1):

[0032] 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1 H 10g of -1,2,4-triazole mesylate was dissolved in 100mL ethyl acetate and 100mL saturated sodium carbonate solution, then shaken and separated, and the organic layer was washed once with 50mL saturated sodium carbonate solution and 50mL saturated sodium chloride solution. , dried over anhydrous sodium sulfate. Filtration, evaporation of the solvent to give intermediate 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1 H -1,2,4-triazole.

[0033] Put a magnet into a 50mL single-necked bottle, add 10mL absolute ethanol and 0.21mL diethylamine (2mmol). After 10 min of ice-water bath, 0.12 mL of carbon disulfide (2 mmol) was added dropwise under rapid magnetic stirring, and kept stirring in the ice bath for 30 min...

Embodiment 2

[0076] Embodiment 2 Pharmacological experiments of compounds of the present invention

[0077] (1) Experimental method

[0078] Conventional in vitro antibacterial test methods are used, see: Antimicrob Agents Chemother 1995,39(5):1169 for details.

[0079] (1) Experimental strains

[0080] In this experiment, the following 8 common human pathogenic standard fungal strains were selected as screening objects:

[0081] Deep fungi: Candida albicans, Cryptococcus neoformans, Candida glabrata, Candida parapsilosis;

[0082] Superficial fungi: Trichophyton rubrum;

[0083] Subcutaneous fungi: Microsporum gypsum, Aspergillus fumigatus.

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Abstract

The invention provides an azole antifungal compound and its pharmaceutically acceptable salt. The structural general formula of the azole antifungal compound is as shown in the specification, wherein R is selected from various aliphatic primary amine or secondary amine, aromatic primary amine or secondary amine and various substituted phenylpiperazine; the substituent group on phenyl of the substituted phenylpiperazine is hydrogen, alkyl group, halogen, cyanogroup, nitro-group, amino group or alkoxy group, is arranged at ortho, meta or para position of phenyl ring, and is monosubstituted or polysubstituted; the alkyl group is the alkyl group with 1-4 carbon atoms; the halogen is selected from F, Cl, Br or I; and the alkoxy group is selected from methoxy, ethoxy and t-butyl oxygroup. The compound provided by the invention has strong antifungal activity to deep fungi. In comparison with present antifungal drugs applied in clinic, the compound provided by the invention has advantages of high efficiency, low toxicity, wide antifungal spectrum and the like. Thus, the compound can be applied to prepare antifungal drugs. A preparation method of the compound is simple and has high yield. The prepared compound has a good antifungal effect.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical compounds, in particular to an azole antifungal compound and its preparation method and application. Background technique [0002] In recent years, with the widespread application of broad-spectrum antibiotics, antineoplastic drugs, and immunosuppressants, the widespread development of peritoneal dialysis, organ transplantation, and radiotherapy, and the rapid spread of immunodeficiency diseases, especially AIDS, Candida albicans, Cryptography neoformans The incidence of opportunistic deep fungal infections such as coccus and Aspergillus fumigatus has increased dramatically. Deep fungal infection has risen to the third largest infectious disease clinically, seriously threatening human life and health. Most of the antifungal drugs currently used in clinical practice have the disadvantages of large toxic and side effects, narrow antibacterial spectrum, and easy drug resistance. Effective ant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08C07D401/12A61K31/4196A61K31/454A61K31/5377A61K31/496A61P31/10
Inventor 胡宏岗邹燕李任武廖万青潘玮华吴秋业赵庆杰俞世冲黄婷吴茂诚
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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