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Bistriazolone, bistriadimenol compounds with antimicrobial activity, and salts, synthesis method and uses thereof

An anti-microbial, compound technology, applied in the direction of organic active ingredients, chemicals for biological control, botanical equipment and methods, etc., can solve problems such as serious drug resistance

Inactive Publication Date: 2010-09-01
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the existing and under-researched azole drugs still have certain limitations in terms of efficacy and toxicity, especially the increasing drug resistance, forcing the majority of drug workers to strengthen the research and development of new drugs

Method used

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  • Bistriazolone, bistriadimenol compounds with antimicrobial activity, and salts, synthesis method and uses thereof
  • Bistriazolone, bistriadimenol compounds with antimicrobial activity, and salts, synthesis method and uses thereof
  • Bistriazolone, bistriadimenol compounds with antimicrobial activity, and salts, synthesis method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Compound I-1: 3-(2,4-dichlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole)acetone

[0043] (0.88g, 0.004mol) 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole) ethanone, potassium carbonate (0.70g, 0.005mol), tetrabutyl Ammonium bromide (25 mg), 20 mL of tetrahydrofuran were placed in a 150 mL three-necked round bottom flask, and stirred at room temperature for 1 h. (1.45 g, 0.007 mol) 2,4-dichlorobenzyl chloride was added, and the temperature of the oil bath was controlled at 45° C. and stirred for 8 h. During the reaction process, the acidity of the reaction solution was constantly checked to keep the pH value greater than 9. Use thin-layer chromatography (developer: chloroform / acetone 10 / 1, V / V) to follow the reaction. After the reaction is stopped, distill off tetrahydrofuran, extract with chloroform (20mL×3), dry over anhydrous sodium sulfate, and concentrate the mother liquor to obtain the initial product , silica gel column chromatography (developer...

Embodiment 2

[0058] Example 2: Compound II-1: 2-(2,4-dichlorophenyl)-3-(2,4-dichlorophenyl)-1-(2,4-difluorophenyl)-2- (1H-1,2,4-triazole)acetone

[0059] 1.17g, (0.005mol) 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole) ethanone, sodium hydroxide (0.63g, 0.015mol), four Butylammonium bromide 50mg, 10mL tetrahydrofuran and 10mL H 2 O was placed in a 250mL three-neck round bottom flask and stirred at room temperature for 1h. (2.45 g, 0.013 mol) 2,4-dichlorobenzyl chloride was added, and the temperature of the oil bath was controlled at 45° C. and stirred for 6 h. During the reaction process, the acidity of the reaction solution was constantly checked to keep the pH value greater than 9. Use thin-layer chromatography (developer: chloroform / acetone 10 / 1, V / V) to track the reaction. When the reaction is complete, distill off tetrahydrofuran, extract with chloroform (20mL×3), dry over anhydrous sodium sulfate, filter, and concentrate the mother liquor to obtain 3.64 g of the initial product was...

Embodiment 3

[0072] Example 3: Compound III-1: 3,3'-(1,4-phenyl)bis(1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole )acetone

[0073] 1.17g (0.005mol) 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole) ethanone, sodium hydroxide (0.63g, 0.015mol), tetrabutyl 50 mg of ammonium bromide, 10 mL of benzene and 10 mL of water were placed in a 250 mL three-necked round bottom flask, and stirred at room temperature for 1 h. Add (2.45 g, 0.013 mol) p-dibenzyl bromide, and stir in an oil bath at 45° C. for 6 h. During the reaction process, the acidity of the reaction solution was constantly checked to keep the pH value greater than 9. Use thin-layer chromatography (developing solvent: chloroform / acetone 10 / 1, V / V) to track the reaction. When the reaction is complete, evaporate the solvent under reduced pressure, extract with chloroform (20mL×3), dry over anhydrous sodium sulfate, filter, and the mother liquor Concentrate to obtain 3.64 g of the initial product, and perform silica gel column chromatography ...

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Abstract

The invention relates to a synthesis method of novel triazolone, triadimenol compounds, namely novel triazolone compound is obtained by subjecting phenyl or substituted phenyl, as raw material, to Friedel-Crafts acylation, triazole alkylation and halogenated benzylation; and novel triadimenol compound is obtained by carbonyl reduction of the triazolone compound. The invention further relates to uses of the novel triazolone and triadimenol compounds as medicines and agricultural chemicals.

Description

[0001] The present invention is a divisional application of the invention patent with application number 2008100700357. technical field [0002] The present invention relates to the synthesis method of triadimefon and triadimefol compounds with antimicrobial activity and the application in medicine and pesticide. Background technique [0003] Medical background: In today's era when science and technology have made great progress, infectious diseases are still the leading factors of morbidity and mortality in the world. Due to the increasingly serious problem of drug resistance in the body, the effective treatment of anti-infective drugs has been compromised, and both the general healthy population and immunocompromised patients are more susceptible to opportunistic infections. Antibacterial, antifungal, and antiviral drugs currently used clinically for the treatment of infectious diseases are facing major challenges. [0004] Azole antifungal drugs are the largest class of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A61K31/4196A61P31/10A61P31/04A01N43/653A01P3/00A01P1/00
Inventor 周成合罗燕
Owner SOUTHWEST UNIVERSITY
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