Indolyl-3-ethanone-α-thioethers: A promising new class of non-toxic antimalarial agents

Eur J Med Chem. 2016 May 23:114:79-88. doi: 10.1016/j.ejmech.2016.02.056. Epub 2016 Mar 3.

Abstract

The success of chemotherapeutics in easing the burden of malaria is under continuous threat from ever-evolving parasite resistance, including resistance to artemisinin combination therapies. Therefore, the discovery of new classes of antimalarials which inhibit new biological targets is imperative to controlling malaria. Accordingly, we report here the discovery of indolyl-3-ethanone-α-thioethers, a new class of antimalarial compounds with encouraging activity. Synthesis of a focused library of compounds revealed important insight into the SAR of this class of compounds, including critical information regarding the position and chemical nature of substituents on both the thiophenol and indole rings. This investigation ultimately led to the discovery of two hit compounds (16 and 27) which exhibited nano molar in vitro antimalarial activity coupled to no observable toxicity against a HeLa cell line.

Keywords: Antimalarial; Indolyl-3-ethanone-α-thioethers; Plasmodium falciparum; Selective inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Dose-Response Relationship, Drug
  • HeLa Cells
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Malaria / drug therapy*
  • Malaria / parasitology*
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Structure-Activity Relationship
  • Sulfides / chemical synthesis
  • Sulfides / chemistry
  • Sulfides / pharmacology*

Substances

  • Antimalarials
  • Indoles
  • Sulfides
  • indolyl-3-ethanone-alpha-thioether