Synthesis and antiprotozoal activity of novel 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives

Bioorg Med Chem Lett. 2013 Jul 15;23(14):4221-4. doi: 10.1016/j.bmcl.2013.05.012. Epub 2013 May 15.

Abstract

A series of 19 new 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives was synthesized starting from the properly substituted 1,2-phenylendiamine. These compounds have hydrogen or methyl at position 1; while hydrogen, chlorine, ethoxy or methoxycarbonyl group is at position 5 and/or 6. The novel compounds were tested against protozoa Trichomonas vaginalis, Giardia intestinalis and Entamoeba histolytica. Experimental evaluations revealed strong activity for all tested compounds, having IC50 values in the nanomolar range, which were even better than metronidazole, the drug of choice for these parasites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry*
  • Benzimidazoles / pharmacology
  • Drug Design
  • Entamoeba histolytica / drug effects
  • Giardia lamblia / drug effects
  • Metronidazole / pharmacology
  • Phenylenediamines / chemistry
  • Structure-Activity Relationship
  • Trichomonas vaginalis / drug effects

Substances

  • Antiprotozoal Agents
  • Benzimidazoles
  • Phenylenediamines
  • Metronidazole
  • 1,2-diaminobenzene
  • benzimidazole