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

2011; Elsevier BV; Volume: 46; Issue: 9 Linguagem: Inglês

10.1016/j.ejmech.2011.06.036

1768-3254

Fábio P. L. Silva, Priscilla Anne Castro de Assis, Cláudio Gabriel Lima-Júnior, Natália G. de Andrade, Saraghina Maria Donato da Cunha, Márcia Rosa de Oliveira, Mário L. A. A. Vasconcellos,

Traditional and Medicinal Uses of Annonaceae

We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC50), cytotoxicity assays in macrophages (CC50), and selectivity index (SICC50/IC50) 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, IC50 = 7.52 μg/mL or 28.38 μM; CC50 = 35.77 μg/mL or 134.98 μM; SI = 4.75) and 2-[Hydroxy(2-nitrophenyl)hydroxyethyl] propanoate (9, IC50 = 5.48 μg/mL or 20.52 μM; CC50 = 29.81 μg/mL or 111.64c μM and, SI = 5.43) were the most effective and safe evaluated compounds.