Sugar hydrazide imides: a new family of glycosidase inhibitors

Abstract

The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3S,4S,5R,6R)-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-imino-1-(methylamino)piperidine acetate presented here behave as inhibitors of α/β-glucosidases in the low micromolar concentration range. The former inhibitor displays a pH-dependent inhibition of β-glucosidase. The N-methylated counterpart behaves as an anomer-selective competitive micromolar inhibitor of α-glucosidase.