RESUMO
The aim of the present study was to evaluate the potential pharmacological and toxicological properties of (E)-1-(1-(methylthio)-1-(selenopheny) hept-1-en-2-yl) pyrrolidin-2-one (compound 1), an organoselenium compound. In vitro experiments showed that compound 1 presented a reduction in the lipid peroxidation induced by Fe²âº in thiobarbituric acid-reactive species (TBARS) production, and in the generation of reactive species caused by Fe²âº/malonate in DCFH-DA oxidation. The high dose (500 mg/kg) induced an increase on ALT but not on AST activity. Hepatic, but not cerebral, δ-ALA-D activity from mice treated with 500 mg/kg presented a significant inhibition. Brain catalase activity was significantly inhibited by 100 mg/kg whereas hepatic catalase activity showed a significant increase at all doses. Hepatic lipid peroxidation was diminished only at lowest dose (100 mg/kg) whereas for brain tissue, all doses induced a significant reduction in TBARS levels. Brain and liver ascorbic acid contents were increased only at highest dose of compound 1. Urea and creatinine levels were not significantly altered by treatments. This is a promising compound with antioxidant activity and low toxicity, suggesting the potential beneficial activity of compound 1 against oxidative damage in many parameters studied in rats and mice.
Assuntos
Antioxidantes/farmacologia , Compostos Organosselênicos/farmacologia , Alanina Transaminase/sangue , Análise de Variância , Animais , Antioxidantes/toxicidade , Ácido Ascórbico/metabolismo , Aspartato Aminotransferases/sangue , Encéfalo/efeitos dos fármacos , Encéfalo/enzimologia , Catalase/metabolismo , Creatinina/sangue , Compostos Ferrosos/farmacologia , Peroxidação de Lipídeos/efeitos dos fármacos , Fígado/efeitos dos fármacos , Fígado/enzimologia , Masculino , Camundongos , Compostos Organosselênicos/toxicidade , Oxidantes/farmacologia , Sintase do Porfobilinogênio/metabolismo , Ratos , Ratos Wistar , Espécies Reativas de Oxigênio/metabolismo , Substâncias Reativas com Ácido Tiobarbitúrico/metabolismo , Extratos de Tecidos , Ureia/sangueRESUMO
We present here carbon-nitrogen bond formation via a coupling reaction of 2-iodo-selenophene catalyzed by Cu(I) in the presence of a base and an inexpensive ligand, and establish the first route to obtaining 2-nitrogen-selenophene derivatives in good yields. We can anticipate that this reaction works well with oxazolidinones, lactams, and aliphatic and aromatic amides, as nitrogen sources, in the absence of any supplementary additives. In addition, the reaction proceeded cleanly under mild reaction conditions and was sensitive to the ratio of amide/2-iodo-selenophene, as well as the nature of the ligand, base, and solvent.
