Synthesis and antimalarial evaluation of new 1,4-bis(3-aminopropyl)piperazine derivatives

Bioorg Med Chem Lett. 2003 Nov 3;13(21):3783-7. doi: 10.1016/j.bmcl.2003.07.008.

Abstract

Synthesis and evaluation of the activity of a new family of 1,4-bis(3-aminopropyl)piperazine derivatives against a chloroquine-resistant strain of Plasmodium falciparum, and as inhibitors of beta-hematin formation, are described. The highest antimalarial activities were obtained for compounds displaying the highest predicted vacuolar accumulation ratios and the best potencies as inhibitors of beta-hematin formation. The most potent compound displayed an activity 3-fold better than chloroquine for a comparable selectivity index upon MRC-5 cells. Therefore, in this series, the replacement of the 7-chloroquinoline group can constitute a strong rationale for further investigation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology*
  • Cell Line
  • Cell Survival / drug effects
  • Chloroquine / pharmacology
  • Drug Resistance
  • Hemeproteins / antagonists & inhibitors
  • Hemeproteins / biosynthesis
  • Humans
  • Indicators and Reagents
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology*
  • Plasmodium falciparum / drug effects
  • Structure-Activity Relationship
  • Vacuoles / drug effects

Substances

  • Antimalarials
  • Hemeproteins
  • Indicators and Reagents
  • Piperazines
  • hemozoin
  • 1,4-bis(3-aminopropyl)piperazine
  • Chloroquine