Synthesis and antidepressant-like activity of selenophenes obtained via iron(III)-PhSeSePh-mediated cyclization of Z-selenoenynes |
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Authors: | Gai Bibiana M Stein André L Roehrs Juliano A Bilheri Filipe N Nogueira Cristina W Zeni Gilson |
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Affiliation: | Laboratório de Síntese, Reatividade, Avalia??o Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria-Rio Grande do Sul, Brasil. |
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Abstract: | We present here the synthesis and antidepressant-like action of a series of 2,5-disubstituted-3-(organoseleno)-selenophenes prepared by a novel synthetic route, the FeCl(3)-diorganyl dichalcogenide-mediated intramolecular cyclization of (Z)-chalcogenoenynes. The cyclized products were obtained in good yields. The results showed that 2c, 2d, 2e and 2o, evaluated in the mouse forced-swimming test, elicited an antidepressant-like activity. The studies clearly show that the phenyl group at the 2-position and an organoselenium group at the 3-position of the selenophene ring are essential for the antidepressant-like activity of selenophenes. A close inspection of the results also revealed that the fluorophenyl portion in the organoselenium group is fundamental for the antidepressant-like action of this class of organochalcogens. |
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