Synthesis and glycosidase inhibitory activity of 1-amino-3,6-anhydro-1-deoxy-D-sorbitol derivatives

3,6-Anhydro-1-(aryl or alkylamino)-1-deoxy-D-sorbitol derivatives have been prepared in four steps from isosorbide, a by-product from the starch industry. The inhibitory activities of these new compounds have been evaluated towards 13 glycosidases. A first lead-compound was identified, which inhibited beta-N-acetylglucosaminidase from bovine kidney (82% inhibition at 1 mM). (C) 2009 Elsevier Inc. All rights reserved.