Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles

Eur J Med Chem. 2012 Feb;48:296-304. doi: 10.1016/j.ejmech.2011.12.028. Epub 2011 Dec 27.

Abstract

1,2,4-Oxadiazole and 1,2,3-triazole containing heterocyclic compounds continue to gain interest in synthesis of chemical entities and exhibit various biological activities as anti-protozoal and anti-cancer agents. By using the principle of bioisosterism, a series of novel oxadiazolyl pyrrolo triazole diones; namely, (3aS,6aR)-1-((3-(4-substituted phenyl)-1,2,4-oxadiazol-5-yl)methyl)-5-phenyl-1,6a-dihydropyrrolo[3,4-d][1,2,3] triazole-4,6(3aH,5H)-diones (5a-k) was designed and synthesized by the 1,3-dipolar cycloaddition reaction of novel 5-azidomethyl 3-aryl substituted 1,2,4-oxadiazoles (4a-k) with N-phenyl maleimide. The structures of all the cycloadducts were elucidated by means of spectroscopic methods and physical characteristics. The in vitro anti-protozoal and cytotoxic activities of these novel heterocyclic compounds were investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology
  • Cell Line
  • Eukaryota / drug effects*
  • Eukaryota / growth & development
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Protozoan Infections / drug therapy
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Rats
  • Spectrometry, Mass, Electrospray Ionization
  • Spectroscopy, Fourier Transform Infrared
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Antiprotozoal Agents
  • Oxadiazoles
  • Pyrroles
  • Triazoles