title: Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita-Baylis-Hillman adducts.
abstract: 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.
authors.affiliation: Laboratório de Síntese Orgânica Medicinal da Paraíba, Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa PB 58059-900, Brazil.
authors.forename: Fábio P L
authors.initials: FP
authors.lastname: Silva
authors.forename: Priscilla A C
authors.initials: PA
authors.lastname: de Assis
authors.forename: Claudio G L
authors.initials: CG
authors.lastname: Junior
authors.forename: Natália G
authors.initials: NG
authors.lastname: de Andrade
authors.forename: Saraghina M D
authors.initials: SM
authors.lastname: da Cunha
authors.forename: Márcia R
authors.initials: MR
authors.lastname: Oliveira
authors.forename: Mário L A A
authors.initials: ML
authors.lastname: Vasconcellos
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002478:Cells, Cultured; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D008264:Macrophages / Q000469:parasitology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D013055:Spectrophotometry, Infrared
chemical_list: D000981:Antiprotozoal Agents