RESUMO
Structure-activity relationship studies on oleanolic acid (1) have resulted in facile syntheses of its new C-28 esters 2-7 by way of one-pot reaction of 1 with a variety of alkylating agents. Oleanolic acid and its new esters were studied for their in vitro antiproliferative effect on healthy human peripheral blood mononuclear cell isolated phytohemagglutinin activated T cells. Results showed that compounds 1, 3, and 5 exhibited significant inhibitory activity on T-cell proliferation. Compound 5 was found to be the most potent, with an IC50 value of 4.249 µg/mL, among all tested compounds, and its activity could be attributed to the presence of bromine atom in the molecule.
Assuntos
Proliferação de Células/efeitos dos fármacos , Citostáticos/síntese química , Ésteres/síntese química , Ácido Oleanólico/análogos & derivados , Linfócitos T/efeitos dos fármacos , Células Cultivadas , Citostáticos/farmacologia , Ésteres/farmacologia , Humanos , Concentração Inibidora 50 , Linfócitos T/fisiologiaRESUMO
Eleven oxazolone derivatives were synthesized and characterized by (1)H NMR, EI, IR and UV spectroscopic and CHN analysis. Three compounds, 4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one (11), 4-[(E)-(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one (12) and 4-[(E)-(4-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) were screened for phagocyte chemiluminescence, neutrophil chemotaxis, T-cell proliferation, cytokine production from mononuclear cells and cytotoxicity. 4-[(E)-(4-Nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) was found to be the most potent immunomodulator in the series.
