Synthesis and evaluation of new antimalarial analogues of quinoline alkaloids derived from Cinchona ledgeriana Moens ex Trimen

Bioorg Med Chem Lett. 2002 May 20;12(10):1351-5. doi: 10.1016/s0960-894x(02)00173-7.

Abstract

In the course of attempts to develop antimalarial drugs, we have designed and synthesized a series of quinoline alkaloide derivatives. Three of them, N-(4-methoxy-3,5-di-tert-butylbenzyl)cinchonidinium bromide (OSL-5), O-benzyl-N-(3,5-di-tert-butyl-4-methoxybenzyl)cinchonidinium bromide (OSL-7), and N-(3,5-di-tert-butyl-4-methoxybenzyl)quininium bromide (OSL-14) show potent activity against Plasmodium falciparum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Chloroquine / pharmacology
  • Cinchona Alkaloids / chemical synthesis*
  • Drug Design
  • Drug Resistance
  • Erythrocytes / parasitology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Plasmodium / drug effects
  • Quinolines / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Cinchona Alkaloids
  • Quinolines
  • Chloroquine