Synthesis of novel 3-(1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-5(4H)-one as antifungal agents

Jaiprakash N Sangshetti; Rahul R Nagawade; Devanand B Shinde

doi:10.1016/j.bmcl.2009.04.134

Synthesis of novel 3-(1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-5(4H)-one as antifungal agents

Bioorg Med Chem Lett. 2009 Jul 1;19(13):3564-7. doi: 10.1016/j.bmcl.2009.04.134. Epub 2009 May 3.

Authors

Jaiprakash N Sangshetti¹, Rahul R Nagawade, Devanand B Shinde

Affiliation

¹ Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004, Maharashtra, India.

PMID: 19464891
DOI: 10.1016/j.bmcl.2009.04.134

Abstract

A novel series of 1,2,3 triazole compounds possessing 1,2,4 oxadiazole ring were efficiently synthesized. Synthesized compounds were evaluated for their in vitro antifungal activities using standard cup plate method. SAR for the series has been developed by comparing their MIC values with miconazole and fluconazole. Compound 11a from the series was more potent than miconazole against Candida albicans (MIC-20) and Aspergillus flavus (MIC-10) whereas equipotent with miconazole against Fusarium oxysporum (MIC-25) and Aspergillus niger (MIC-12.5). Also compound 11h was more potent than miconazole against Candida albicans (MIC-20) and Aspergillus niger (MIC-10) and equipotent with miconazole against Fusarium oxysporum. Compound 11h was equipotent with fluconazole against Aspergillus niger (MIC-10).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology
Fluconazole / pharmacology
Miconazole / pharmacology
Microbial Sensitivity Tests
Oxadiazoles / chemical synthesis*
Oxadiazoles / chemistry
Oxadiazoles / pharmacology
Structure-Activity Relationship
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology

Substances

Antifungal Agents
Oxadiazoles
Triazoles
Miconazole
Fluconazole