Synthesis and Leishmanicidal Activity of Molecular Hybrids 1,2,3-Triazole-Chalcones

Abstract

Leishmaniasis is a largely neglected infection caused by Leishmania spp. parasites. The first-line treatment, antimoniate meglumine, has a large number of adverse effects, high cost and is resistance development, hence the necessity of new alternatives. We report the synthesis of (2E)-1-[1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-3-arylprop-2-en-1-one derivatives and the in-vitro evaluation of their leishmanicidal activities. A series of 16 compounds were synthesized in three steps starting from p-anisidine with moderate to good yields and their biological activities were evaluated in-vitro against Leishmania mexicana promastigotes and RAW 264.7 cells. The synthesis of 1,2,3-triazol and chalcone moieties were made using a cycloaddition with acetylacetone followed by a Claisen-Schmidt condensation using different substituted benzaldehydes. Nine compounds were active against L. mexicana with IC50 between 1.0-29.2 µM.

Evaluation of the Anti-Leishmania mexicana and -Trypanosoma brucei Activity and Mode of Action of 4,4′-(Arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)

“…The leishmanicidal activity against promastigotes from L. mexicana was evaluated by measuring parasites’ mitochondrial activity using the MTT (Thiazolyl Blue Tetrazolium Bromide) colorimetric assay as described previously [ 26 , 36 , 37 ]. Promastigotes were cultured at 25 °C in Schneider’s Drosophila Medium (Gibco) supplemented with 10% fetal bovine serum (Eurobio).…”