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通过铁(III)催化的二苯硒醚与炔烃加成得到的双乙烯基硒化物:合成与镇痛活性。

Bis-vinyl selenides obtained via iron(III) catalyzed addition of PhSeSePh to alkynes: synthesis and antinociceptive activity.

机构信息

Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.

出版信息

Org Biomol Chem. 2013 Feb 21;11(7):1199-208. doi: 10.1039/c2ob27064a.

Abstract

In the present study the synthesis and antinociceptive activity of bis-vinyl selenides, prepared via FeCl(3) promoted reaction addition of diorganyl dichalcogenides to alkynes, is described. The pharmacological results demonstrated that bis-vinyl selenides 3a, 3d, 3h and 3t elicited antinociceptive effect in the mouse formalin test. The antinociceptive effects of bis-vinyl selenides are not sensitive to electronic effects of the substituents on the aromatic ring directly bonded to the selenium atom. Bis-vinyl selenides 3h and 3t were the most promising molecules for pharmacological purposes since these bis-vinyl selenides were effective in both phases of the formalin test and against edema. A single dose of bis-vinyl selenides 3a, 3d, 3h and 3t did not cause acute toxicity in mice.

摘要

在本研究中,描述了通过 FeCl(3) 促进的二芳基二硫化物与炔烃的反应加成合成双-乙烯基硒化物,并研究了其镇痛活性。药理结果表明,双-乙烯基硒化物 3a、3d、3h 和 3t 在小鼠福尔马林试验中表现出镇痛作用。双-乙烯基硒化物的镇痛作用对与硒原子直接键合的芳环上取代基的电子效应不敏感。双-乙烯基硒化物 3h 和 3t 是最有前途的药理学分子,因为这些双-乙烯基硒化物在福尔马林试验的两个阶段以及对抗水肿都有效。单剂量的双-乙烯基硒化物 3a、3d、3h 和 3t 不会引起小鼠急性毒性。

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