Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
學年 99
學期 2
出版（發表）日期 2011-02-01
作品名稱 Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
作品名稱（其他語言）
著者 Shih, Tzenge-lien; Liang, Ming-tsung; Wu, Kuen-da; Lin, Chun-hung
單位 淡江大學化學學系
出版者 Oxford: Pergamon
著錄名稱、卷期、頁數 Carbohydrate Research 346(2), pp.183-190
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.
關鍵字 Azepane; d-(−)-Quinic acid; β-Galactosidase; Glycosidase inhibitor
語言 en
ISSN 0008-6215
期刊性質 國外
收錄於 EI SCI
產學合作
通訊作者 Shih, Tzenge-lien; Lin, Chun-hung
審稿制度
國別 GBR
公開徵稿
出版型式 紙本
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