Synthesis and structure-activity relationships of 2-phenyl-1-[(pyridinyl- and piperidinylmethyl)amino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents

Francis Giraud; Rémi Guillon; Cédric Logé; Fabrice Pagniez; Carine Picot; Marc Le Borgne; Patrice Le Pape

doi:10.1016/j.bmcl.2008.11.101

Synthesis and structure-activity relationships of 2-phenyl-1-[(pyridinyl- and piperidinylmethyl)amino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents

Bioorg Med Chem Lett. 2009 Jan 15;19(2):301-4. doi: 10.1016/j.bmcl.2008.11.101. Epub 2008 Dec 3.

Authors

Francis Giraud¹, Rémi Guillon, Cédric Logé, Fabrice Pagniez, Carine Picot, Marc Le Borgne, Patrice Le Pape

Affiliation

¹ Université de Nantes, Nantes Atlantique Universités, Département de Pharmacochimie, Cibles et Médicaments des Infections, de l'Immunité et du Cancer, IICIMED-EA 1155, UFR de Sciences Pharmaceutiques, 1 rue Gaston Veil, Nantes F-44035 Cedex 1, France.

PMID: 19091558
DOI: 10.1016/j.bmcl.2008.11.101

Abstract

Continuous efforts on the synthesis and structure-activity relationships (SARs) studies of modified 1-benzylamino-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents, allowed identification of new 1-[(pyridinyl- and piperidinylmethyl)amino] derivatives with MIC(80) values ranging from 1410.0 to 23.0ngmL(-1) on Candidaalbicans. These results confirmed both the importance of pi-pi stacking and hydrogen bonding interactions in the active site of CYP51-C. albicans.

MeSH terms

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

Substances

Antifungal Agents
Propanols