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

Zoltán Czakó; László Juhász; Agnes Kenéz; Katalin Czifrák; László Somsák; Tibor Docsa; Pál Gergely; Sándor Antus

doi:10.1016/j.bmc.2009.07.052

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

Bioorg Med Chem. 2009 Sep 15;17(18):6738-41. doi: 10.1016/j.bmc.2009.07.052. Epub 2009 Jul 25.

Authors

Zoltán Czakó¹, László Juhász, Agnes Kenéz, Katalin Czifrák, László Somsák, Tibor Docsa, Pál Gergely, Sándor Antus

Affiliation

¹ Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, PO Box 20, Hungary.

PMID: 19703777
DOI: 10.1016/j.bmc.2009.07.052

Abstract

A series of N-(beta-D-glucopyranosyl)amides 5d-i were synthesized by PMe(3) mediated Staudinger reaction of O-peracetylated beta-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.

Publication types

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

MeSH terms

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

Substances

Amides
Dioxanes
Glycogen Phosphorylase, Muscle Form