Three-dimensional quantitative structure-activity relationship (QSAR) and receptor mapping of cytochrome P-450(14 alpha DM) inhibiting azole antifungal agents

J Chem Inf Comput Sci. Mar-Apr 1999;39(2):204-10. doi: 10.1021/ci9800413.


Molecular modeling was performed by a combined use of conformational analysis and 3D-QSAR methods to distinguish structural attributes common to a series of azole antifungal agents. Apex-3D program was used to recognize the common biophoric structural patterns of 13 diverse sets of azole antifungal compounds demonstrating different magnitudes of biological activity. Apex-3D identified three common biophoric features significant for activity: N1 atom of azole ring, the aromatic ring centroid 1, and aromatic ring centroid 2. A common biophore model proposed from the Apex-3D analysis can be useful for the design of novel cytochrome P-450(14 alpha DM) inhibiting antifungal agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Azoles / chemistry*
  • Azoles / pharmacology*
  • Binding Sites
  • Cytochrome P-450 Enzyme Inhibitors*
  • Drug Design
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Models, Molecular
  • Molecular Conformation
  • Oxidoreductases / antagonists & inhibitors*
  • Static Electricity
  • Sterol 14-Demethylase
  • Structure-Activity Relationship


  • Antifungal Agents
  • Azoles
  • Cytochrome P-450 Enzyme Inhibitors
  • Enzyme Inhibitors
  • Oxidoreductases
  • Sterol 14-Demethylase