Optimization of 2-Anilino 4-Amino Substituted Quinazolines into Potent Antimalarial Agents with Oral in Vivo Activity

J Med Chem. 2017 Feb 9;60(3):1171-1188. doi: 10.1021/acs.jmedchem.6b01673. Epub 2017 Jan 26.

Abstract

Novel antimalarial therapeutics that target multiple stages of the parasite lifecycle are urgently required to tackle the emerging problem of resistance with current drugs. Here, we describe the optimization of the 2-anilino quinazoline class as antimalarial agents. The class, identified from publicly available antimalarial screening data, was optimized to generate lead compounds that possess potent antimalarial activity against P. falciparum parasites comparable to the known antimalarials, chloroquine and mefloquine. During the optimization process, we defined the functionality necessary for activity and improved in vitro metabolism and solubility. The resultant lead compounds possess potent activity against a multidrug resistant strain of P. falciparum and arrest parasites at the ring phase of the asexual stage and also gametocytogensis. Finally, we show that the lead compounds are orally efficacious in a 4 day murine model of malaria disease burden.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Antimalarials / administration & dosage
  • Antimalarials / pharmacology
  • Antimalarials / therapeutic use*
  • Disease Models, Animal
  • Mice
  • Plasmodium falciparum / drug effects
  • Quinazolines / administration & dosage
  • Quinazolines / pharmacology
  • Quinazolines / therapeutic use*
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Quinazolines