Synthesis and trypanocidal activity of novel 2,4,5-triaryl-N-hydroxylimidazole derivatives

Molecules. 2013 Mar 15;18(3):3445-57. doi: 10.3390/molecules18033445.

Abstract

Herein, we report the design, synthesis and trypanocidal activity of some novel trisubstituted imidazole derivatives. These heterocyclic derivatives were structurally planned by exploring the concept of molecular hybridisation between two arylhydrazones derived from megazol, which has potent trypanocidal activity. The trypanocidal activity of these triarylimidazole derivatives was evaluated against infective trypomastigote forms of T. cruzi and the derivative 2'-(4-bromophenyl)-1-methyl-5'-phenyl-1H,3'H-2,4'-biimidazol-3'-ol showed moderate biological activity (IC50 = 23.9 µM) when compared to benznidazole, a standard trypanocidal drug. These compounds did not present cytotoxic effects at concentrations near the trypanocidal IC50, being considered a good starting point for the development of new anti-Chagas drug candidates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cell Survival / drug effects
  • Drug Evaluation, Preclinical
  • Hydrazones / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / drug effects

Substances

  • Hydrazones
  • Imidazoles
  • Trypanocidal Agents