General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)
General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-α-C-glycosides)
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DOI：
10.1016/j.bmc.2004.12.043
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发表时间：
2005-03-15
影响因子：
3.5
通讯作者：
Asano, N
中科院分区：
文献类型：
--
作者：
Goujon, JY;Gueyrard, D;Asano, N
描述了通过氮丙啶与各种杂原子亲核试剂（包括硫醇、胺、醇、羧酸盐和磷酸盐）的开环反应来合成荞麦碱的α-1-C-取代衍生物（2-脱氧野尻霉素-α-C-糖苷）的一般方法。以三-O-苄基-D-葡萄糖醛为起始原料，经九步反应，总收率为14-28%。报道了荞麦碱的α-1-C-取代衍生物、α-高野尻霉素的2-脱氧类似物19及其1，N-脱水衍生物22作为糖苷酶抑制剂的生物学评价。发现糖基磷酸模拟物15 k对糖原磷酸化酶B和磷酸葡萄糖变位酶没有抑制活性。(c)2005爱思唯尔有限公司保留所有权利。
A general synthesis of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is described. The nine-step reaction sequence proceeded in an overall yield of 14-28% from tri-O-benzyl-D-glucal. Biological evaluation of alpha-1-C-substituted derivatives of fagomine, of the 2-deoxy analog of alpha-homonojirimycin 19 and its 1,N-anhydro derivative 22 as glycosidase inhibitors is reported. The glycosyl phosphate mimetic 15k was found to display no inhibitory activity towards glycogen phosphorylase b and phosphoglucomutase. (c) 2005 Elsevier Ltd. All rights reserved.