Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: chemical and biological studies

Bioorg Med Chem. 2008 Mar 15;16(6):2984-91. doi: 10.1016/j.bmc.2007.12.049. Epub 2007 Dec 25.

Abstract

We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that mesoionic hydrochloride MI possesses the best activity profile. Compound MI may be a prototype for use in the development of a new chemotherapeutic agent with high efficiency, which may be employed in the treatment of Chagas' disease.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology*
  • Animals
  • Benzodioxoles / chemistry*
  • Benzodioxoles / pharmacology*
  • Chagas Disease / drug therapy
  • Macrophages / parasitology
  • Mice
  • Piperidines / chemistry*
  • Piperidines / pharmacology*
  • Polyunsaturated Alkamides / chemistry*
  • Polyunsaturated Alkamides / pharmacology*
  • Structure-Activity Relationship
  • Trypanocidal Agents / chemistry*
  • Trypanosoma cruzi / drug effects

Substances

  • Alkaloids
  • Benzodioxoles
  • Piperidines
  • Polyunsaturated Alkamides
  • Trypanocidal Agents
  • piperine