Design, synthesis, and evaluation of 1-(N-benzylamino)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents

Francis Giraud; Cédric Logé; Fabrice Pagniez; Damien Crepin; Patrice Le Pape; Marc Le Borgne

doi:10.1016/j.bmcl.2008.02.027

Design, synthesis, and evaluation of 1-(N-benzylamino)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1820-4. doi: 10.1016/j.bmcl.2008.02.027. Epub 2008 Feb 14.

Authors

Francis Giraud¹, Cédric Logé, Fabrice Pagniez, Damien Crepin, Patrice Le Pape, Marc Le Borgne

Affiliation

¹ Université de Nantes, Nantes Atlantique Universités, Département de Pharmacochimie, Biomolécules et Cibles Thérapeutiques, BioCiT-EA 1155, UFR de Sciences Pharmaceutiques, 1 rue Gaston Veil, Nantes, F-44035 Cedex 1, France.

PMID: 18313295
DOI: 10.1016/j.bmcl.2008.02.027

Abstract

A series of 1-(N-benzylamino)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols 6a-c, 7a-c, 8a, and 9a were prepared in five steps and evaluated for their antifungal activity. The most active compound 7b was docked into a home-made 3D model of the targeted enzyme confirming the importance of Tyr118, His377, and Ser378 residues in its binding mode.

Publication types

Evaluation Study

MeSH terms

Antifungal Agents / chemical synthesis*
Antifungal Agents / pharmacology*
Aspergillus fumigatus / drug effects*
Candida albicans / drug effects*
Drug Design*
Microbial Sensitivity Tests
Models, Molecular
Propanols / chemical synthesis*
Propanols / pharmacology*
Structure-Activity Relationship

Substances

Antifungal Agents
Propanols