l-Isofucoselenofagomine and derivatives: dual activities as antioxidants and as glycosidase inhibitors

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• 作者：Pené ; lope Merino-Montiel ; Ó ; scar Ló ; pez ; ^{osc-lopez@us.es} ; José ; G. Ferná ; ndez-Bolañ ; os
• 关键词：Selenosugars ; Antioxidants ; Glycosidase inhibitors ; Glutathione peroxidase mimic ; Non-bonded interactions
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：6 May, 2012
• 卷：68
• 期：18
• 页码：3591-3595
• 文件大小：580 K

摘要

The synthesis of a series of l-fuco-configured selenosugars, isosters of the potent glycosidase inhibitor isofucofagomine has been accomplished by a double nucleophilic displacement of a dimesylated derivative with selenide anion generated in situ. Se-Alkylation and oxidation of the corresponding selenane afforded a selenonium and a selenoxide, respectively. The biological activities of such compounds have been evaluated, finding a dual activity caused by the presence of the selenium atom: the selenane exerted a good glutathione peroxidase mimicry by efficiently scavenging H₂O₂ in the presence of thiols, whereas the stable selenoxide derivative was found to be the first example of a selenosugar acting as a good 伪-l-fucosidase inhibitor.