Dihydroquinazolinone inhibitors of proliferation of blood and liver stage malaria parasites

Antimicrob Agents Chemother. 2014;58(3):1516-22. doi: 10.1128/AAC.02148-13. Epub 2013 Dec 23.

Abstract

Drugs that target both the liver and blood stages of malaria will be needed to reduce the disease's substantial worldwide morbidity and mortality. Evaluation of a 259-member library of compounds that block proliferation of the blood stage of malaria revealed several scaffolds--dihydroquinazolinones, phenyldiazenylpyridines, piperazinyl methyl quinolones, and bis-benzimidazoles--with promising activity against the liver stage. Focused structure-activity studies on the dihydroquinazolinone scaffold revealed several molecules with excellent potency against both blood and liver stages. One promising early lead with dual activity is 2-(p-bromophenyl)-3-(2-(diethylamino)ethyl)-2,3-dihydroquinazolin-4(1H)-one with 50% effective concentrations (EC50s) of 0.46 μM and 0.34 μM against liver stage Plasmodium berghei ANKA and blood stage Plasmodium falciparum 3D7 parasites, respectively. Structure-activity relationships revealed that liver stage activity for this compound class requires a 3-dialkyl amino ethyl group and is abolished by substitution at the ortho-position of the phenyl moiety. These compounds have minimal toxicity to mammalian cells and are thus attractive compounds for further development.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Humans
  • Life Cycle Stages / drug effects
  • Liver / parasitology*
  • Malaria / blood
  • Malaria / drug therapy
  • Malaria / parasitology
  • Plasmodium / drug effects*
  • Plasmodium / growth & development
  • Plasmodium berghei / drug effects
  • Plasmodium falciparum / drug effects
  • Quinazolines / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Quinazolines