Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity

Molecules. 2015 Aug 13;20(8):14761-76. doi: 10.3390/molecules200814761.

Abstract

Six novel imidazoline derivatives were synthesized and tested in antifungal assays. One of the compounds, N-cyclohexyl-2-imino-3-(4-nitrophenyl)imidazolidine-1-carboxamide showed moderate activity against several clinical strains of Candida albicans. Its structure was solved by X-ray crystallography and its mode of action was deduced using molecular modelling. It was found to be similar to that of fluconazole. The potential for further optimization including SAR of the compound is briefly discussed.

Keywords: 14-α-sterol demethylase; Candida albicans; X-ray analysis; antifungal; molecular modelling; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects
  • Clotrimazole / pharmacology
  • Hydrogen Bonding
  • Imidazolines / chemical synthesis*
  • Imidazolines / chemistry
  • Imidazolines / pharmacology*
  • Isocyanates / chemistry
  • Microbial Sensitivity Tests
  • Models, Molecular*
  • Molecular Conformation
  • Molecular Dynamics Simulation

Substances

  • Antifungal Agents
  • Imidazolines
  • Isocyanates
  • Clotrimazole