Antimalarial agents against both sexual and asexual parasites stages: structure-activity relationships and biological studies of the Malaria Box compound 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine (MMV019918) and analogues

Eur J Med Chem. 2018 Apr 25;150:698-718. doi: 10.1016/j.ejmech.2018.03.024. Epub 2018 Mar 10.

Abstract

Therapies addressing multiple stages of Plasmodium falciparum life cycle are highly desirable for implementing malaria elimination strategies. MMV019918 (1, 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine) was selected from the MMV Malaria Box for its dual activity against both asexual stages and gametocytes. In-depth structure-activity relationship studies and cytotoxicity evaluation led to the selection of 25 for further biological investigation. The potential transmission blocking activity of 25 versus P. falciparum was confirmed through the standard membrane-feeding assay. Both 1 and 25 significantly prolonged atrioventricular conduction time in Langendorff-isolated rat hearts, and showed inhibitory activity of Ba2+ current through Cav1.2 channels. An in silico target-fishing study suggested the enzyme phosphoethanolamine methyltransferase (PfPMT) as a potential target. However, compound activity against PfPMT did not track with the antiplasmodial activity, suggesting the latter activity relies on a different molecular target. Nevertheless, 25 showed interesting activity against PfPMT, which could be an important starting point for the identification of more potent inhibitors active against both sexual and asexual stages of the parasite.

Keywords: Gametocytes; Inhibition; Malaria; Plasmodium falciparum; Structure-activity relationships.

MeSH terms

  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology*
  • Life Cycle Stages / drug effects
  • Malaria, Falciparum / drug therapy*
  • Malaria, Falciparum / parasitology
  • Methyltransferases / antagonists & inhibitors
  • Methyltransferases / metabolism
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Piperidines / chemical synthesis
  • Piperidines / chemistry
  • Piperidines / pharmacology*
  • Plasmodium falciparum / drug effects*
  • Structure-Activity Relationship

Substances

  • 1-(5-(4-bromo-2-chlorophenyl)furan-2-yl)-N-((piperidin-4-yl)methyl)methanamine
  • Antimalarials
  • Enzyme Inhibitors
  • Furans
  • Piperidines
  • Methyltransferases
  • phosphoethanolamine methyltransferase