Synthesis of novel triazole derivatives as inhibitors of cytochrome P450 14alpha-demethylase (CYP51)

Eur J Med Chem. 2007 Sep;42(9):1226-33. doi: 10.1016/j.ejmech.2007.01.006. Epub 2007 Jan 24.

Abstract

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substitutedphenyl)-piperazin-1-yl]-propan-2-ols have been designed and synthesized on the basis of the structure-activity relationships and antimycotic mechanism of azole antifungal agents. Their structures were confirmed by elemental analysis, IR, MS and (1)H NMR. Results of preliminary antifungal tests against eight human pathogenic fungi (Candida albicans, Candida parapsilosis, Candida tropicalis, Cryptococcus neoformans, Aspergillus fumigatus, Trichophyton rubrum, Fonsecaea compacta, and Microsporum gypseum) in vitro showed that all title compounds exhibited activity against fungi tested to some extent. Among the compounds tested, all compounds showed higher activity against C. albicans than fluconazole in vitro. Compounds 3, 6-8, 28, 29, and 32 exhibited the same activities against C. albicans as voriconazole (with the MIC value of 0.0152microg/mL). Compounds 3, 6, and 7 showed higher activity against C. parapsilosis than all five positive controls.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Cytochrome P-450 Enzyme System / chemical synthesis*
  • Cytochrome P-450 Enzyme System / pharmacology*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology*

Substances

  • Antifungal Agents
  • Enzyme Inhibitors
  • Triazoles
  • Cytochrome P-450 Enzyme System