Synthesis and glycosidase inhibitory activity of some N-Substituted 6-Deoxy-5a-carba-β- - and -galactopyranosylamines

Chemical modification of 5a-carba-β- -fucopyranosylamine (3) generated six N-substituted derivatives 9a–f, among which N-octyl 9b, decyl 9c, and phenylbutyl ones 9f were found to be very strong β-galactosidase as well as β-glucosidase inhibitors. The inhibitory activity appeared attributable to -enantiomers from biological assays of prepared -enantiomers. Therefore, 6-deoxy-5a-carba-β- -galactopyranosylamine (D-3) might be a promising lead compound for further design of new carba sugar-type β-galactosidase inhibitors.