Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (−)-vibo-quercitol

In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-l-talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-l-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate α-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.

5-Amino-5-deoxy-1-O-methyl-l-talo-quercitol (5), an analogue of strong α-fucosidase inhibitor 5a-carba-fucopyranosylamine (3), was synthesized and shown to be a moderate α-fucosidase inhibitor.Figure optionsDownload as PowerPoint slide