Synthesis and glycogen phosphorylase inhibitory activity of N-(β-d-glucopyranosyl)amides possessing 1,4-benzodioxane moiety

Zoltán Czakó, László Juhász, Ágnes Kenéz, Katalin Czifrák, László Somsák, Tibor Docsa, Pál Gergely, Sándor Antus

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Abstract

A series of N-(β-d-glucopyranosyl)amides 5d-i were synthesized by PMe3 mediated Staudinger reaction of O-peracetylated β-d-glucopyranosyl azide (1) followed by acylation with carboxylic acids 3d-i and subsequent Zemplén deacetylation. The new compounds were tested for their inhibitory activity against rabbit muscle glycogen phosphorylase and the structure-activity relationships of these compounds are also discussed in this paper.

Original languageEnglish
Pages (from-to)6738-6741
Number of pages4
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number18
DOIs
Publication statusPublished - Sep 15 2009

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Keywords

  • Benzodioxane
  • Glycogen phosphorylase
  • Inhibitor
  • N-(β-d-Glucopyranosyl)amide

ASJC Scopus subject areas

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

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