Aminoazabenzimidazoles, a novel class of orally active antimalarial agents

J Med Chem. 2014 Jul 10;57(13):5702-13. doi: 10.1021/jm500535j. Epub 2014 Jun 24.

Abstract

Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg·kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Benzimidazoles / pharmacokinetics
  • Benzimidazoles / pharmacology
  • Benzimidazoles / therapeutic use*
  • Biological Availability
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • High-Throughput Screening Assays
  • Humans
  • Inhibitory Concentration 50
  • Malaria, Falciparum / drug therapy*
  • Mice
  • Plasmodium falciparum / drug effects*
  • Small Molecule Libraries
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Benzimidazoles
  • Small Molecule Libraries