Short synthesis of new salacinol analogues and their evaluation as glycosidase inhibitors

被引:34
作者
Gallienne, E
Benazza, M
Demailly, G
Bolte, J
Lemaire, M
机构
[1] Univ Clermont Ferrand, Lab SEESIB, UMR 6504, F-63177 Clermont Ferrand, France
[2] Univ Picardie, Lab Glucides, FRE 2779, F-80039 Amiens, France
关键词
salacinol; glycosidsase inhibitors; cyclic sulfate; thiaanhydroalditol; zwitterion; sulfonium sulfate inner salt;
D O I
10.1016/j.tet.2005.03.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Versatile synthesis of some analogues of the naturally-occurring alpha-glucosidase inhibitor salacinol (1), involving thioanhydro alditol moieties with erythro, D,L-threo, xylo, ribo, D-arabino and D-manno configurations is described. Nucleophilic attack at the least-hindered carbon atom of an L- or D-protected erythritol cyclic sulfate by the thioanhydro alditol sulfur atom yielded the desired zwitterionic compounds. In addition, the preparation of the cyclic sulfates of 2,4-O-benzylidene-D-erythritol and 2,4-Ow-isopropylidene-L-erythritol was improved. Enzyme inhibition tests showed that most of the new compounds were weak but specific inhibitors, while good inhibitory activity was found for a six-membered ring analogue (beta-glucosidase: K-i = 16 mu M). (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4557 / 4568
页数:12
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