New azoles with antifungal activity: Design, synthesis, and molecular docking

Xiaoyun Chai; Jun Zhang; Yongbing Cao; Yan Zou; Qiuye Wu; Dazhi Zhang; Yuanying Jiang; Qingyan Sun

doi:10.1016/j.bmcl.2010.12.006

New azoles with antifungal activity: Design, synthesis, and molecular docking

Bioorg Med Chem Lett. 2011 Jan 15;21(2):686-9. doi: 10.1016/j.bmcl.2010.12.006. Epub 2010 Dec 7.

Authors

Xiaoyun Chai¹, Jun Zhang, Yongbing Cao, Yan Zou, Qiuye Wu, Dazhi Zhang, Yuanying Jiang, Qingyan Sun

Affiliation

¹ Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Guohe Road 325, Shanghai 200433, People's Republic of China.

PMID: 21190856
DOI: 10.1016/j.bmcl.2010.12.006

Abstract

In order to search for many target compounds with excellent activities, a series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluoro-phenyl)-3-[(4-substituted phenyl)-piperazin-1-yl]-propan-2-ols were designed, synthesized, and evaluated as antifungal agents. Results of preliminary antifungal tests against eight human pathogenic fungi in vitro showed that all the title compounds exhibited excellent activities with broad spectrum. Moreover, a molecular model for the binding between 5a and the active site of CACYP51 was provided based on the computational docking results.

Publication types

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

MeSH terms

14-alpha Demethylase Inhibitors / chemical synthesis
14-alpha Demethylase Inhibitors / chemistry*
14-alpha Demethylase Inhibitors / pharmacology*
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry*
Antifungal Agents / pharmacology*
Azoles / chemical synthesis
Azoles / chemistry*
Azoles / pharmacology*
Fungi / drug effects*
Fungi / enzymology
Humans
Microbial Sensitivity Tests
Models, Molecular
Mycoses / drug therapy
Protein Binding
Sterol 14-Demethylase / chemistry
Sterol 14-Demethylase / metabolism
Structure-Activity Relationship

Substances

14-alpha Demethylase Inhibitors
Antifungal Agents
Azoles
Sterol 14-Demethylase