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    题名: Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
    作者: Shih, Tzenge-lien;Liang, Ming-tsung;Wu, Kuen-da;Lin, Chun-hung
    贡献者: 淡江大學化學學系
    关键词: Azepane;d-(−)-Quinic acid;β-Galactosidase;Glycosidase inhibitor
    日期: 2011-02
    上传时间: 2011-10-15 23:37:02 (UTC+8)
    出版者: Oxford: Pergamon
    摘要: An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from d-(−)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against β-galactosidase (IC50 = 3 μM). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities.
    關聯: Carbohydrate Research 346(2), pp.183-190
    DOI: 10.1016/j.carres.2010.11.014
    显示于类别:[化學學系暨研究所] 期刊論文


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