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

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.

Figure optionsDownload as PowerPoint slide