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Sulfur/nitrogen-containing azole antifungal compound as well as preparation method and application of sulfur-containing azoles antifungal compound

A compound and antifungal technology, applied in the field of medicine, to achieve the effect of high yield, good effect and strong antifungal activity

Inactive Publication Date: 2014-08-27
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

But so far no azole compound N-alkyl-N-(2-(2,4-difluorophenyl)-2-hydroxyl-3-(1 H Report on -1,2,4-triazol-1-yl))-propyl-aminodithiocarbamic acid benzyl ester or its salts

Method used

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  • Sulfur/nitrogen-containing azole antifungal compound as well as preparation method and application of sulfur-containing azoles antifungal compound
  • Sulfur/nitrogen-containing azole antifungal compound as well as preparation method and application of sulfur-containing azoles antifungal compound
  • Sulfur/nitrogen-containing azole antifungal compound as well as preparation method and application of sulfur-containing azoles antifungal compound

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Experimental program
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Effect test

Embodiment 1

[0033] Embodiment 1 Preparation of the compound of the present invention

[0034] (1) 1-(1 H -1, 2, 4-triazol-1-yl)-2-(2, 4-difluorophenyl)-3-( N -Methylamino)-2-ol

[0035] 1-[2-(2, 4-difluorophenyl)-2, 3-epoxypropyl]-1 H -1, 2, 4-triazole methanesulfonate 21g, with methylamine 10mL, triethylamine 20mL, heated to reflux in 300mL ethanol for 6-8 hours, distilled off the solvent after the reaction, extracted with 200mL ethyl acetate, 100mL×2 washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated to remove ethyl acetate to obtain oily 1-(1 H -1, 2, 4-triazol-1-yl)-2-(2, 4-difluorophenyl)-3-( N -Methylamino)-2-ol 11.96g, yield 68.0%.

[0036] Preparation of N-methyl-N-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1 H -1,2,4-triazol-1-yl))-propyl-aminodithiocarbamate benzyl ester (compound 6a in Table 1):

[0037] In a 50mL single-necked bottle, put a magnet, add 10mL absolute ethanol, 0.536 g 1-(1 H -1, 2, 4-triazol-1-yl)-2-(2, 4-difluorophenyl)-3-( ...

Embodiment 2

[0124] Embodiment 2 Pharmacological experiments of compounds of the present invention

[0125] (1) Experimental method

[0126] Conventional in vitro antibacterial test methods are used, see: Antimicrob Agents Chemother 1995,39(5):1169 for details.

[0127] (1) Experimental strains

[0128] In this experiment, the following 8 common human pathogenic standard fungal strains were selected as screening objects:

[0129] Deep fungi: Candida albicans, Cryptococcus neoformans, Candida glabrata, Candida parapsilosis;

[0130] Superficial fungi: Trichophyton rubrum;

[0131] Subcutaneous fungi: Microsporum gypsum, Aspergillus fumigatus.

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PUM

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Abstract

The invention is a sulfur / nitrogen-containing azole antifungal compound as well as a preparation method and an application of the sulfur / nitrogen-containing azole antifungal compound, relates to the technical field of medicine. The sulfur / nitrogen-containing azole antifungal compound is a novel azole antifungal compound and has a chemical structural formula which is shown in the specification, wherein, R1 is hydrogen or a straight-chain or branched-chain saturated or unsaturated lower alkyl having 1-6 carbon atoms; R2 is selected from hydrogen, alkyl, halogen, cyano group, a nitro group, an amino and an alkoxy, can be located at the ortho, meta or para position of the benzene ring and can be monosubstituted or polysubstituted. The invention also provides a preparation method and an application of the compound. The compound disclosed by the invention has strong antifungal activity on the deep fungal, has the advantages of high efficiency, low toxicity, broad anti-fungal spectrum and the like compared with the current clinically applied antifungal drugs, and therefore, the compound can be used for the preparation of efficient antifungal agents.

Description

technical field [0001] The invention relates to the field of medical technology, and is a novel azole antifungal compound—N-alkyl-N-(2-(2,4-difluorophenyl)-2-hydroxyl-3-(1 H -1,2,4-triazol-1-yl))-propyl-aminodithiocarbamic acid benzyl ester compounds and salts thereof, as well as their preparation methods and uses. 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 pra...

Claims

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Application Information

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IPC IPC(8): C07D249/08A61K31/4196A61P31/10
CPCC07D249/08
Inventor 邹燕潘炜华廖万清赵庆杰胡宏岗吴秋业吴茂诚李翔潘博宋阳俞世冲柴晓云
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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