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

Eva Bokor; Tibor Docsa; Pál Gergely; László Somsák

doi:10.1016/j.bmc.2009.12.043

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

Bioorg Med Chem. 2010 Feb;18(3):1171-80. doi: 10.1016/j.bmc.2009.12.043. Epub 2009 Dec 22.

Authors

Eva Bokor¹, Tibor Docsa, Pál Gergely, László Somsák

Affiliation

¹ Department of Organic Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.

PMID: 20080412
DOI: 10.1016/j.bmc.2009.12.043

Abstract

1-(D-Glucopyranosyl)-1,2,3-triazoles were prepared from per-O-acetylated alpha- and beta-D-glucopyranosyl azides as well as per-O-benzoylated (beta-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 beta-D-glucopyranosyl derivatives were superior inhibitors as compared to the two other series of triazoles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Glucosides / chemical synthesis
Glucosides / chemistry*
Glucosides / pharmacology*
Glycogen Phosphorylase, Muscle Form / antagonists & inhibitors*
Glycogen Phosphorylase, Muscle Form / metabolism*
Molecular Conformation
Rabbits
Structure-Activity Relationship
Triazoles / chemical synthesis
Triazoles / chemistry*
Triazoles / pharmacology*

Substances

Glucosides
Triazoles
Glycogen Phosphorylase, Muscle Form