Synthesis of 1-( d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors

Abstract

1-( d-Glucopyranosyl)-1,2,3-triazoles were prepared from per- O-acetylated α- and β- d-glucopyranosyl azides as well as per- O-benzoylated (β- d- gluco-hept-2-ulopyranosylazide)onamide and onic acid methylester by using azide-alkyne cycloaddition catalysed by in situ generated Cu(I) under aqueous conditions. The O-acyl protecting groups were removed by the Zemplén protocol. The test compounds were assayed against rabbit muscle glycogen phosphorylase b to show that the β- d-glucopyranosyl derivatives were superior inhibitors as compared to the two other series of triazoles.