High selective leishmanicidal activity of 3-hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile and analogous compounds

Eur J Med Chem. 2007 Jan;42(1):99-102. doi: 10.1016/j.ejmech.2006.07.013. Epub 2006 Sep 28.

Abstract

Sixteen not new aromatic compounds were prepared by one-pot reaction i.e. through Baylis-Hillman reaction and were the first time evaluated against promastigote Leishmania amazonensis and infected mammalian cells. Most of the compounds were selectively more active against amastigotes than the reference drug sodium stibogluconate (Pentostam, IC(50)=44.7 microM). We found that 3-hydroxy-2-methylene-3-(4-bromophenyl) propanenitrile (13) was the most active (IC(50)=12.5 microM) and safer compound (0.0 (0.9); % macrophage LDH release), being the lead compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • In Vitro Techniques
  • Leishmania / drug effects*
  • Macrophages, Peritoneal / drug effects
  • Macrophages, Peritoneal / parasitology
  • Mice
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology
  • Structure-Activity Relationship
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology

Substances

  • 3-hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile
  • Nitriles
  • Trypanocidal Agents