Carbon analogs of antifungal dioxane-triazole derivatives: synthesis and in vitro activities

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6538-41. doi: 10.1016/j.bmcl.2008.10.055. Epub 2008 Oct 15.

Abstract

A new series of triazole compounds possessing a carbon atom in place of a sulfur atom were efficiently synthesized and their in vitro antifungal activities were investigated. The carbon analogs showed excellent in vitro activity against Candida, Cryptococcus, and Aspergillus species. The MICs of compound 1c against C. albicans ATCC24433, C. neoformans TIMM1855, and A. fumigatus ATCC26430 were 0.016, 0.016, and 0.125 microg/mL, respectively (MICs of fluconazole: 0.5, >4, and >4 microg/mL; MICs of itraconazole: 0.125, 0.25, and 0.25 microg/mL).

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Carbon / chemistry*
  • Chemistry, Pharmaceutical / methods
  • Dioxanes / chemistry*
  • Drug Design
  • Epoxy Compounds / chemistry
  • Fluconazole / chemical synthesis
  • Fluconazole / pharmacology
  • Humans
  • In Vitro Techniques
  • Itraconazole / chemical synthesis
  • Itraconazole / pharmacology
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Stereoisomerism
  • Triazoles / chemistry*

Substances

  • Antifungal Agents
  • Dioxanes
  • Epoxy Compounds
  • Triazoles
  • Itraconazole
  • Carbon
  • Fluconazole