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有机硒化合物:化学及其在有机合成中的应用

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis.

作者信息

Sonego Juan M, de Diego Sheila I, Szajnman Sergio H, Gallo-Rodriguez Carola, Rodriguez Juan B

机构信息

Departamento de Química Orgánica Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, C1428EHA, Buenos Aires, Argentina.

CONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica (UMYMFOR), C1428EHA, Buenos Aires, Argentina.

出版信息

Chemistry. 2023 Sep 15;29(52):e202300030. doi: 10.1002/chem.202300030. Epub 2023 Aug 10.

Abstract

Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium-containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium-containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

摘要

硒最初被描述为一种毒素,后来却被证明是生命中至关重要的微量元素,它以硒代半胱氨酸及其二聚体硒代胱氨酸的形式存在。从药物研发的角度来看,含硒药物是硫和氧的电子等排体,其优势在于硒原子的存在赋予了抗氧化性能和高亲脂性,这会增加细胞膜通透性,从而带来更好的口服生物利用度。在本文中,我们重点关注了硒原子的相关特性,尤其是获取各种有机硒分子的相应合成方法以及所提出的反应机理。还将探讨硒糖的制备及其生物学特性,包括硒糖苷、硒核苷、硒肽和其他含硒化合物。我们试图将硒化学最重要的方面和有趣的例子浓缩在一篇文章中。

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