Potent antimalarial 4-pyridones with improved physico-chemical properties

Bioorg Med Chem Lett. 2011 Sep 15;21(18):5214-8. doi: 10.1016/j.bmcl.2011.07.044. Epub 2011 Jul 23.

Abstract

Antimalarial 4-pyridones are a novel class of inhibitors of the plasmodial mitochondrial electron transport chain targeting Cytochrome bc1 (complex III). In general, the most potent 4-pyridones are lipophilic molecules with poor solubility in aqueous media and low oral bioavailability in pre-clinical species from the solid dosage form. The strategy of introducing polar hydroxymethyl groups has enabled us to maintain the high levels of antimalarial potency observed for other more lipophilic analogues whilst improving the solubility and the oral bioavailability in pre-clinical species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Chemistry, Physical
  • Crystallography, X-Ray
  • Dogs
  • Dose-Response Relationship, Drug
  • Hydrogen-Ion Concentration
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Pyridones / chemical synthesis
  • Pyridones / chemistry*
  • Pyridones / pharmacology*
  • Solubility
  • Stereoisomerism

Substances

  • Antimalarials
  • Pyridones
  • 4-pyridone