Bioorganic & Medicinal Chemistry 2011-07-15

Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: a molecular hybridization approach.

Ticiano P Barbosa, Suervy C O Sousa, Francianne M Amorim, Yara K S Rodrigues, Priscilla A C de Assis, John P A Caldas, Márcia R Oliveira, Mário L A A Vasconcellos

文献索引：Bioorg. Med. Chem. 19 , 4250-6, (2011)

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摘要

The chalcone-like series 1a-1g was efficiently synthesized from Morita-Baylis-Hillman reaction (52-74% yields). Compounds 1a-1g were designed by molecular hybridization based on the anti-inflammatory drug methyl salicylate (3) and the antileishmanial moiety of the Morita-Baylis-Hillman adducts 2a-2g. The 1a-1g compounds were much more actives than precursor series 2a-2g, for example, IC(50)=7.65 μM on Leishmania amazonensis and 10.14 μM on Leishmania chagasi (compound 1c) when compared to IC(50)=50.08 μM on L. amazonensis and 82.29 μM on L. chagasi (compound 2c). The IC(50) values of compound 3 (228.49 μM on L. amazonensis and 261.45 μM on L. chagasi) and acryloyl salicylate 4 (108.50 μM on L. amazonensis and 118.83 μM on L. chagasi) were determined here, by the first time, on Leishmania.Copyright © 2011 Elsevier Ltd. All rights reserved.