Novel 2-aryl-3,4,5-trihydroxypiperidines:Synthesis and glycosidase inhibition  

作　　者：Hui Zhao Wu-Bao Wang Shinpei Nakagawa Yue-Mei Jia Xiang-Guo Hu George W.J.Fleet Francis X.Wilson Robert J.Nash Atsushi Kato Chu-Yi Yu 

机构地区：[1]Beijing National Laboratory for Molecular Science (BNLMS),CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sciences [2]Department of Hospital Pharmacy,University of Toyama,2630 Sugitani,Toyama 930-0194,Japan [3]Chemistry Research Laboratory,Department of Chemistry,University of Oxford [4]Summit PLC,91,Milton Park,Abingdon,Oxon OX14 4RY,UK [5]Phytoquest Limited,IBERS,Plas Gogerddan,Ceredigion,Aberystwyth SY23 3EB,Wales,UK

出　　处：《Chinese Chemical Letters》2013年第12期1059-1063,共5页中国化学快报（英文版）

基　　金：Financial support from National Basic Research Program of China (Nos. 2012CB822101 and 2011CB808603);the Natural Science Foundation of China (Nos. 21272240 and 21102149)

摘　　要：Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines （6-8 and their enantiomers）, the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six- membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition （IC50 1080 μmol/L） against β-galactosidase from rat intestinal lactases.Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines （6-8 and their enantiomers）, the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six- membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition （IC50 1080 μmol/L） against β-galactosidase from rat intestinal lactases.

关 键 词：2-Aryl polyhydroxylated piperidine lminosugars Radicamine mimics Glycosidase inhibitors 

分 类 号：O621.3[理学—有机化学]