Indazole N-oxide derivatives as antiprotozoal agents: synthesis, biological evaluation and mechanism of action studies

Bioorg Med Chem. 2006 May 15;14(10):3467-80. doi: 10.1016/j.bmc.2006.01.007. Epub 2006 Feb 17.

Abstract

A series of indazole N-oxide derivatives have been synthesized and their antichagasic and leishmanocidal properties studied. 3-Cyano-2-(4-iodophenyl)-2H-indazole N1-oxide exhibited interesting antichagasic activity on the two parasitic strains and the two parasitic stages evaluated. Furthermore, besides its trypanocidal activity, 3-cyano-2-(4-nitrophenyl)-2H-indazole N1-oxide showed leishmanocidal activity in the three parasitic strains evaluated. To gain insight into the mechanism of action, electrochemical behaviour, ESR experiment, inhibition of parasitic respiration and QSAR were performed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry*
  • Antiprotozoal Agents / pharmacology*
  • Cell Line, Tumor
  • Cells, Cultured
  • Crystallography, X-Ray
  • Electrochemistry
  • Indazoles / chemical synthesis
  • Indazoles / chemistry*
  • Indazoles / pharmacology*
  • Leishmania / drug effects
  • Models, Molecular
  • Parasitic Sensitivity Tests
  • Quantitative Structure-Activity Relationship
  • Trypanosoma cruzi / drug effects

Substances

  • Antineoplastic Agents
  • Antiprotozoal Agents
  • Indazoles