Synthesis and structure-activity relationships for new 6-fluoroquinoline derivatives with antiplasmodial activity

Bioorg Med Chem. 2019 May 15;27(10):2052-2065. doi: 10.1016/j.bmc.2019.03.061. Epub 2019 Apr 2.

Abstract

The substitution of 6-fluoroquinolines was modified in ring positions 2 and 4. The new compounds were tested in vitro for their activities against a sensitive and a multidrug resistant strain of Plasmodium falciparum. Some physicochemical parametres were calculated (log P, log D, ligand efficiency) or determined experimentally (permeability). The most promising compounds were tested for their in vivo activity against Plasmodium berghei in a mouse model. The 6-fluoro-2-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}-N-[2-(pyrrolidin-1-yl)ethyl]quinoline-4-carboxamide possessed proper physicochemical properties and showed high antiplasmodial activity in vitro (IC50 ≤ 0.0029 µM) and in vivo (99.6% activity).

Keywords: Antimalarial; Plasmodium berghei; Plasmodium falciparum; Quinoline derivatives.

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology
  • Antimalarials / therapeutic use
  • Cell Line
  • Cell Survival / drug effects
  • Disease Models, Animal
  • Drug Resistance / drug effects
  • Malaria / drug therapy
  • Mice
  • Parasitic Sensitivity Tests
  • Plasmodium berghei / drug effects
  • Plasmodium berghei / pathogenicity
  • Plasmodium falciparum / drug effects
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Quinolines / therapeutic use
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Quinolines
  • quinoline