3-Position Biaryl Endochin-like Quinolones with Enhanced Antimalarial Performance

ACS Infect Dis. 2024 Jul 12;10(7):2419-2442. doi: 10.1021/acsinfecdis.4c00140. Epub 2024 Jun 11.

Abstract

ELQ-300 is a potent antimalarial drug with activity against blood, liver, and vector stages of the disease. A prodrug, ELQ-331, exhibits reduced crystallinity and improved in vivo efficacy in preclinical testing, and currently, it is in the developmental pipeline for once-a-week dosing for oral prophylaxis against malaria. Because of the high cost of developing a new drug for human use and the high risk of drug failure, it is prudent to have a back-up plan in place. Here we describe ELQ-596, a member of a new subseries of 3-biaryl-ELQs, with enhanced potency in vitro against multidrug-resistant Plasmodium falciparum parasites. ELQ-598, a prodrug of ELQ-596 with diminished crystallinity, is more effective vs murine malaria than its progenitor ELQ-331 by 4- to 10-fold, suggesting that correspondingly lower doses could be used to protect and cure humans of malaria. With a longer bloodstream half-life in mice compared to its progenitor, ELQ-596 highlights a novel series of next-generation ELQs with the potential for once-monthly dosing for protection against malaria infection. Advances in the preparation of 3-biaryl-ELQs are presented along with preliminary results from experiments to explore key structure-activity relationships for drug potency, selectivity, pharmacokinetics, and safety.

Keywords: antimalarial drug; next-generation ELQs; oral prophylaxis; structure−activity relationships.

MeSH terms

  • Animals
  • Antimalarials* / chemistry
  • Antimalarials* / pharmacokinetics
  • Antimalarials* / pharmacology
  • Female
  • Humans
  • Malaria / drug therapy
  • Malaria / prevention & control
  • Malaria, Falciparum / drug therapy
  • Malaria, Falciparum / prevention & control
  • Mice
  • Plasmodium falciparum* / drug effects
  • Prodrugs / chemistry
  • Prodrugs / pharmacokinetics
  • Prodrugs / pharmacology
  • Quinolones* / chemistry
  • Quinolones* / pharmacokinetics
  • Quinolones* / pharmacology
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Quinolones
  • Prodrugs