New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton

J Med Chem. 2008 Oct 9;51(19):6216-9. doi: 10.1021/jm8006905. Epub 2008 Sep 6.

Abstract

The synthesis of the chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, is reported. The tetraoxanes 2, 4, and 8 show relatively potent in vitro antimalarial activities, with IC90 values for the Plasmodium falciparum strain W2 of 2.26, 12.44, and 10.74 nM, respectively. In addition, two compounds, 2 and 4, cured mice in a modified Thompson test for antimalarial blood stage activity, with a minimum curative dose of 80 mg/kg, a minimum active dose of 20 mg/kg/day, and a maximum tolerated dose of >960 mg/kg.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemistry*
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Binding Sites
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Malaria / blood
  • Malaria / drug therapy*
  • Malaria / parasitology
  • Maximum Tolerated Dose
  • Mice
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetraoxanes / chemistry*

Substances

  • Aminoquinolines
  • Antimalarials
  • Tetraoxanes
  • 7-chloro-4-aminoquinoline