title: Synthesis and antidepressant-like activity of selenophenes obtained via iron(III)-PhSeSePh-mediated cyclization of Z-selenoenynes.
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.
authors: Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria-Rio Grande do Sul, Brasil.
authors: Bibiana M
authors: BM
authors: Gai
authors: André L
authors: AL
authors: Stein
authors: Juliano A
authors: JA
authors: Roehrs
authors: Filipe N
authors: FN
authors: Bilheri
authors: Cristina W
authors: CW
authors: Nogueira
authors: Gilson
authors: G
authors: Zeni
mesh_terms: D000818:Animals; D000928:Antidepressive Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013550:Swimming
chemical_list: D000928:Antidepressive Agents; D005290:Ferric Compounds; D016566:Organoselenium Compounds