Synthesis, conformational study, glycosidase inhibitory activity and molecular docking studies of dihydroxylated 4-and 5-amino-iminosugars

An efficient methodology for the synthesis of new amino iminosugars 6a, 7a and 8, starting from D-glucose, is reported. The conformational study using H-1 NMR data showed that the amino iminosugar 6a exists in the C-2(5) while; the 7a and 8 exist in the C-5(2) conformation. The inhibition activities with different glycosidases showed that 6a and 7a are poor glycosidase inhibitors. However, amino iminosugar 8 showed selective inhibition against the beta-galactosidase (IC50 = 43 mu M, Ki = 153 mu M). These results are substantiated by the molecular docking studies. (C) 2015 Elsevier Ltd. All rights reserved.