Acyclic analogues of glucosamidine, 1-deoxynojirimycin and N-(1,3-dihydroxyprop-2-yl) derivative of valiolamine as potential glucosidase inhibitors

The N-(beta-hydroxyethyl)acetamidine (4) was prepared. Mesylation of 8 gave the 1,3-di-O-benzyl-2-O-methanesulfonylglycerol (9). Nucleophilic displace ment of the mesyloxy group in 9 with ethanolamine and morpholine gave 11 an d 12, respectively. Their catalytic hydrogenation gave 2-deoxy-2-(1-hydroxy eth-2-yl)amino-glycerol (5) and 2-deoxy-2-(morpholin-4-yl)glycerol (13). Th e inhibition of the beta-D-glucosidase enzyme from sweet almond by 4, 5 and 13-16 has been studied. (C) 1999 Published by Elsevier Science Ltd. All ri ghts reserved.