Efficient synthesis of 16 aromatic Morita–Baylis–Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi |
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Authors: | Cl udio G.L. Junior, Priscila A.C. de Assis, F bio P.L. Silva, Suervy C.O. Sousa, Nat lia G. de Andrade, Ticiano P. Barbosa, Patrí cia L.N. Nerí s, Luiz V.G. Segundo, Í talo C. Anjos, Gabriel A.U. Carvalho, Gerd B. Rocha, M rcia R. Oliveira,M rio L.A.A. Vasconcellos |
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Affiliation: | a Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil;b Departamento de Biologia Molecular, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil |
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Abstract: | Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA) 1–16 were efficiently synthesized in a one step Morita–Baylis–Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81–100% yields) without the formation of side products on DABCO catalysis and at low temperature (0 °C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC50 values of 6.88 μg mL−1 and 11.06 μg mL−1 respectively on L. amazonensis; 9.58 μg mL−1 and 14.34 μg mL−1 respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds. |
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Keywords: | Leishmania Morita– Baylis– Hillman adducts Temperature effect Drugs Structure– activity-relationship |
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