Synthesis of some 4-substituted 8-amino-6-methoxyquinolines as potential antimalarials

J Med Chem. 1979 Jun;22(6):694-9. doi: 10.1021/jm00192a016.

Abstract

The 4-vinyl, 4-ethyl, and three 4-[beta-(arylthio)ethyl] derivatives of primaquine and other 8-aminoquinoline antimalarial agents were prepared for antimalarial evaluation. 8-[(4'-Amino-1'-methylbutyl)amino]-4-ethyl-6-methoxyquinoline (4-ethylprimaquine), which showed activity approximately equal to that of primaquine against Plasmodia cynomolgi in Rhesus monkey, was the most active of the compounds tested. 4-Ethylprimaquine was also less toxic than primaquine, as measured in the Rane mouse screen.

MeSH terms

  • Aminoquinolines / chemical synthesis*
  • Aminoquinolines / pharmacology
  • Aminoquinolines / therapeutic use
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / therapeutic use
  • Dose-Response Relationship, Drug
  • Haplorhini
  • Macaca mulatta
  • Malaria / drug therapy
  • Malaria / prevention & control
  • Mice
  • Plasmodium berghei
  • Primaquine / therapeutic use

Substances

  • Aminoquinolines
  • Antimalarials
  • Primaquine