New 4-aminoquinoline Mannich base antimalarials. 1. Effect of an alkyl substituent in the 5'-position of the 4'-hydroxyanilino side chain

J Med Chem. 1999 Jul 29;42(15):2747-51. doi: 10.1021/jm9901374.

Abstract

A new series of 4-aminoquinoline Mannich base derivatives have been synthesized, in which the 3'-diethylamino function of amodiaquine (AQ) is replaced by a 3'-tert-butylamino group and an aliphatic hydrocarbon entity is incorporated into the 5'-position of the 4'-hydroxyanilino side chain. Seven alkyl Mannich base derivatives were screened and found to be active against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. The propyl and isopropyl alkyl derivatives were found to be the most active; consequently these derivatives were tested against a nonsensitive strain of Plasmodium berghi in vivo and found to be 3-fold more active than AQ, irrespective of the route of administration (oral or intraperitoneal).

MeSH terms

  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Inhibitory Concentration 50
  • Malaria / drug therapy
  • Male
  • Mannich Bases / chemical synthesis*
  • Mannich Bases / chemistry
  • Mannich Bases / pharmacology
  • Mice
  • Plasmodium berghei
  • Plasmodium falciparum / drug effects
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Structure-Activity Relationship

Substances

  • Aniline Compounds
  • Antimalarials
  • Mannich Bases
  • Quinolines