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

Research output: Contribution to journalArticle

62 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1171-1180
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number3
DOIs
Publication statusPublished - Feb 1 2010

Fingerprint

Glycogen Phosphorylase
Triazoles
Azides
Phosphorylase b
Alkynes
Cycloaddition
Cycloaddition Reaction
Muscle
Rabbits
Derivatives
Muscles
Acids

Keywords

  • 1-(d-Glucopyranosyl)-1,2,3-triazole
  • Azide-alkyne cycloaddition
  • Glycogen phosphorylase
  • Inhibitor

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

@article{6a7204dfd1d54d6193cc8feb385e1aba,
title = "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 Zempl{\'e}n 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.",
keywords = "1-(d-Glucopyranosyl)-1,2,3-triazole, Azide-alkyne cycloaddition, Glycogen phosphorylase, Inhibitor",
author = "{\'E}va Bokor and T. Docsa and P. Gergely and L. Soms{\'a}k",
year = "2010",
month = "2",
day = "1",
doi = "10.1016/j.bmc.2009.12.043",
language = "English",
volume = "18",
pages = "1171--1180",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "3",

}

TY - JOUR

T1 - Synthesis of 1-(d-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors

AU - Bokor, Éva

AU - Docsa, T.

AU - Gergely, P.

AU - Somsák, L.

PY - 2010/2/1

Y1 - 2010/2/1

N2 - 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.

AB - 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.

KW - 1-(d-Glucopyranosyl)-1,2,3-triazole

KW - Azide-alkyne cycloaddition

KW - Glycogen phosphorylase

KW - Inhibitor

UR - http://www.scopus.com/inward/record.url?scp=75449087225&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=75449087225&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2009.12.043

DO - 10.1016/j.bmc.2009.12.043

M3 - Article

C2 - 20080412

AN - SCOPUS:75449087225

VL - 18

SP - 1171

EP - 1180

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 3

ER -