Synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazones, designed as cruzain inhibitors candidates

Bioorg Med Chem. 2009 Jan 15;17(2):641-52. doi: 10.1016/j.bmc.2008.11.065. Epub 2008 Dec 3.

Abstract

In this paper, we report the structural design, synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazone (NAH) derivatives, planned as cruzain inhibitors candidates, a cysteine protease essential for the survival of Trypanosoma cruzi within the host cell. The salicylaldehyde N-acylhydrazones 7a and 8a presented IC(50) values of the same magnitude order than the standard drug nifurtimox (Nfx), when tested in vitro against epimastigote forms of Trypanosoma cruzi (Tulahuen 2 strain) and were non-toxic at the highest assayed doses rendering selectivity indexes (IC(50) (macrophages)/IC(50) (Trypanosoma cruzi)) of >25 for 7a and >20 for 8a, with IC(50) values in macrophages >400 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Cells, Cultured
  • Cysteine Endopeptidases
  • Cysteine Proteinase Inhibitors / chemical synthesis*
  • Hydrazones / chemical synthesis*
  • Inhibitory Concentration 50
  • Macrophages / parasitology
  • Mice
  • Nifurtimox
  • Protozoan Proteins / antagonists & inhibitors*
  • Quinoxalines / chemical synthesis
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / drug effects*

Substances

  • Cysteine Proteinase Inhibitors
  • Hydrazones
  • Protozoan Proteins
  • Quinoxalines
  • Trypanocidal Agents
  • Cysteine Endopeptidases
  • cruzain, Trypanosoma cruzi
  • Nifurtimox