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

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, IC50 = 44.7 mu M). We found that 3-hydroxy-2-methylene-3-(4-broinophenyl)propanenitrile (13) was the most active (IC50 = 12.5 mu M) and safer compound (0.0 (0.9); % macrophage LDH release), being the lead compound. (c) 2006 Elsevier Masson SAS. All rights reserved.