Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita-Baylis-Hillman adducts.

Autor: Silva FP; Laboratório de Síntese Orgânica Medicinal da Paraíba, Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa PB 58059-900, Brazil., de Assis PA, Junior CG, de Andrade NG, da Cunha SM, Oliveira MR, Vasconcellos ML
Jazyk: angličtina
Zdroj: European journal of medicinal chemistry [Eur J Med Chem] 2011 Sep; Vol. 46 (9), pp. 4295-301. Date of Electronic Publication: 2011 Jul 05.
DOI: 10.1016/j.ejmech.2011.06.036
Abstrakt: We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC(50)), cytotoxicity assays in macrophages (CC(50)), and selectivity index (SICC(50)/IC(50)) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the "one pot" Morita-Baylis-Hillman Reaction between the aldehydes 29-36 and the acrylates 27 or 28 under DABCO as promoter. The MBHA 2-[Hydroxy(2-nitrophenyl)propyl] propanoate (1, IC(50) = 7.52 μg/mL or 28.38 μM; CC(50) = 35.77 μg/mL or 134.98 μM; SI = 4.75) and 2-[Hydroxy(2-nitrophenyl)hydroxyethyl] propanoate (9, IC(50) = 5.48 μg/mL or 20.52 μM; CC(50) = 29.81 μg/mL or 111.64c μM and, SI = 5.43) were the most effective and safe evaluated compounds.
(Copyright © 2011 Elsevier Masson SAS. All rights reserved.)
Databáze: MEDLINE
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