New azoles with potent antifungal activity: design, synthesis and molecular docking

Eur J Med Chem. 2009 Oct;44(10):4218-26. doi: 10.1016/j.ejmech.2009.05.018. Epub 2009 May 24.

Abstract

In response to the urgent need for novel antifungal agents with improved activity and broader spectrum, computer modeling was used to rational design novel antifungal azoles. On the basis of the active site of lanosterol 14alpha-demethylase from Candida albicans (CACYP51), a series of new azoles with substituted-phenoxypropyl piperazine side chains were rational designed and synthesized. In vitro antifungal activity assay indicates that the new azoles show good activity against most of the tested pathogenic fungi. Interestingly, the designed compounds are also active against an azole-resistant clinical strain. Compared to fluconazole and itraconazole, several compounds (such as 12i, 12j and 12n) show higher antifungal activity and broader spectrum, which are promising leads for the development of novel antifungal agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Azoles / chemical synthesis
  • Azoles / chemistry*
  • Azoles / pharmacology*
  • Candida albicans / drug effects
  • Candida albicans / enzymology*
  • Catalytic Domain
  • Cytochrome P-450 Enzyme System / chemistry
  • Cytochrome P-450 Enzyme System / metabolism*
  • Drug Design
  • Fungal Proteins / chemistry
  • Fungal Proteins / metabolism*
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Protein Binding
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Azoles
  • Fungal Proteins
  • cytochrome P-450 CYP51, Candida albicans
  • Cytochrome P-450 Enzyme System