Novel design principle validated: glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent

László Somsák; Veronika Nagy; Sébastien Vidal; Katalin Czifrák; Eszter Berzsényi; Jean-Pierre Praly

doi:10.1016/j.bmcl.2008.08.052

Novel design principle validated: glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent

Bioorg Med Chem Lett. 2008 Oct 15;18(20):5680-3. doi: 10.1016/j.bmcl.2008.08.052. Epub 2008 Aug 22.

Authors

László Somsák¹, Veronika Nagy, Sébastien Vidal, Katalin Czifrák, Eszter Berzsényi, Jean-Pierre Praly

Affiliation

¹ Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary. somsak@tigris.unideb.hu

PMID: 18793852
DOI: 10.1016/j.bmcl.2008.08.052

Abstract

2-Naphthyl-substituted glucopyranosylidene-spiro-oxathiazole prepared following a novel design principle was found to be the best known glucose analogue inhibitor of rabbit muscle glycogen phosphorylase b (K(i) 160 nM).

Publication types

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

MeSH terms

Animals
Chemistry, Pharmaceutical / methods*
Drug Design
Glucose / analogs & derivatives*
Glucose / chemical synthesis
Glucose / chemistry*
Glucose / pharmacology
Glycogen / chemistry
Glycogen Phosphorylase / antagonists & inhibitors*
Glycogen Phosphorylase / chemistry
Hypoglycemic Agents / chemical synthesis*
Hypoglycemic Agents / pharmacology
Kinetics
Models, Chemical
Rabbits
Spiro Compounds / chemical synthesis*
Spiro Compounds / pharmacology
Thiazoles / chemical synthesis*
Thiazoles / pharmacology

Substances

Hypoglycemic Agents
Spiro Compounds
Thiazoles
glucopyranosylidene-spiro-oxathiazole
Glycogen
Glycogen Phosphorylase
Glucose