Synthesis and Antileishmanial Activity of 3-(α-Azolylbenzyl)indoles.

The goal of the present study was to evaluate several azolyl-substituted indoles as new antileishmanial agents. Ten 3-(α-azolylbenzyl)indoles have been synthesized using Friedel-Crafts acylation as a key-step. All the target compounds were found to display high levels of activity when tested against Leishmania mexicana promastigotes in vitro . The most active compounds, showing an IC 50 <1 μM, were 5-bromo-1-ethyl-3-[(2,4-dichlorophenyl)(1 H -imidazol-1-yl)methyl]-1 H -indole 15 and its triazole analogue 17 . Four representative compounds 15 , 17 , 22 and, 23 were also tested against intracellular amastigotes of L. mexicana using ketoconazole and meglumine antimoniate as reference compounds, the results of which are discussed. [ABSTRACT FROM AUTHOR]