3,3'-Disubstituted 5,5'-Bi(1,2,4-triazine) Derivatives with Potent in Vitro and in Vivo Antimalarial Activity

J Med Chem. 2019 Mar 14;62(5):2485-2498. doi: 10.1021/acs.jmedchem.8b01799. Epub 2019 Mar 5.

Abstract

A series of 3,3'-disubstituted 5,5'-bi(1,2,4-triazine) derivatives was synthesized and screened against the erythrocytic stage of Plasmodium falciparum 3D7 line. The most potent dimer, 6k, with an IC50 (50% inhibitory concentration) of 0.008 μM, had high in vitro potency against P. falciparum lines resistant to chloroquine (W2, IC50 = 0.0047 ± 0.0011 μM) and artemisinin (MRA1240, IC50 = 0.0086 ± 0.0010 μM). Excellent ex vivo potency of 6k was shown against clinical field isolates of both P. falciparum (IC50 = 0.022-0.034 μM) and Plasmodium vivax (IC50 = 0.0093-0.031 μM) from the blood of outpatients with uncomplicated malaria. Despite 6k being cleared relatively rapidly in mice, it suppressed parasitemia in the Peters 4-day test, with a mean ED50 value (50% effective dose) of 1.47 mg kg-1 day-1 following oral administration. The disubstituted triazine dimer 6k represents a new class of orally available antimalarial compounds of considerable interest for further development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / pharmacokinetics
  • Antimalarials / pharmacology*
  • Chloroquine / pharmacology
  • Drug Resistance
  • Humans
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy / methods
  • Mice
  • Molecular Structure
  • Plasmodium / classification
  • Plasmodium / drug effects
  • Species Specificity
  • Structure-Activity Relationship
  • Triazines / chemistry
  • Triazines / pharmacokinetics
  • Triazines / pharmacology*

Substances

  • Antimalarials
  • Triazines
  • Chloroquine