Synthesis, analytical behaviour and biological evaluation of new 4-substituted pyrrolo[1,2-a]quinoxalines as antileishmanial agents

Bioorg Med Chem. 2007 Jan 1;15(1):194-210. doi: 10.1016/j.bmc.2006.09.068. Epub 2006 Oct 1.

Abstract

An original series of 4-substituted pyrrolo[1,2-a]quinoxaline derivatives, new structural analogues of Galipea species quinoline alkaloids, was synthesized from various substituted 2-nitroanilines via multistep heterocyclizations and tested for in vitro antiparasitic activity upon Leishmania amazonensis and Leishmania infantum strains. Structure-activity relationships enlighten the importance of the 4-substituted alkenyl side chain on the pyrrolo[1,2-a]quinoxaline moiety to modulate the antileishmanial activity.

MeSH terms

  • Animals
  • Antiprotozoal Agents* / chemical synthesis
  • Antiprotozoal Agents* / chemistry
  • Antiprotozoal Agents* / pharmacology
  • Crystallography, X-Ray
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Leishmania / drug effects*
  • Leukocytes, Mononuclear / drug effects
  • Models, Molecular
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Quinoxalines* / chemical synthesis
  • Quinoxalines* / chemistry
  • Quinoxalines* / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antiprotozoal Agents
  • Quinoxalines