Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

淡江大學機構典藏 > 理學院 > 化學學系暨研究所 > 期刊論文 > Item 987654321/61753

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題名:	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
貢獻者:	淡江大學化學學系
關鍵詞:	Azepane;d-(−)-Quinic acid;β-Galactosidase;Glycosidase inhibitor
日期:	2011-02
上傳時間:	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
顯示於類別:	[化學學系暨研究所] 期刊論文

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