4-Aminoquinoline-chalcone/-N-acetylpyrazoline conjugates: Synthesis and antiplasmodial evaluation

Eur J Med Chem. 2017 Sep 29:138:993-1001. doi: 10.1016/j.ejmech.2017.07.041. Epub 2017 Jul 22.

Abstract

1H-1,2,3-triazole linked 4-aminoquinoline-chalcone/-N-acetylpyrazoline conjugates were synthesized and evaluated against cultured chloroquine (CQ) resistant strain. Antiplasmodial activities of the synthesized conjugates revealed dependence of activity on the length of the alkyl chain as well as on the presence of methoxy substituents on ring A/ring B of the chalcone. The most potent and non-cytotoxic conjugate showed comparable antiplasmodial activity with that of CQ, with an IC50 value of 53.7 nM.

Keywords: 4-Aminoquinoline; Antiplasmodial; Chalcone; Click chemistry; N-acetylpyrazoline.

MeSH terms

  • Aminoquinolines / chemistry
  • Aminoquinolines / pharmacology*
  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Dose-Response Relationship, Drug
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Aminoquinolines
  • Antimalarials
  • Pyrazoles
  • Chalcone
  • 4-aminoquinoline