Beta-C-glycosiduronic acids and beta-C-glycosyl compounds: new PTP1B inhibitors

Li Lin; Qiang Shen; Guo-Rong Chen; Juan Xie

doi:10.1016/j.bmcl.2008.10.091

Beta-C-glycosiduronic acids and beta-C-glycosyl compounds: new PTP1B inhibitors

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6348-51. doi: 10.1016/j.bmcl.2008.10.091. Epub 2008 Nov 1.

Authors

Li Lin¹, Qiang Shen, Guo-Rong Chen, Juan Xie

Affiliation

¹ PPSM, ENS Cachan, CNRS, UniverSud, 61 av President Wilson, F-94230 Cachan, France.

PMID: 18993066
DOI: 10.1016/j.bmcl.2008.10.091

Abstract

Beta-C-glycosiduronic acid quinones and beta-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl beta-C-glycosyl compounds (18, 22, 23 and 34) showed IC(50) values of 0.77-5.27 microM against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent.

MeSH terms

Carbohydrates / chemistry
Chemistry, Pharmaceutical / methods
Diabetes Mellitus / drug therapy
Drug Design
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / pharmacology*
Glycosides / chemistry*
Glycosides / pharmacology
Humans
Inhibitory Concentration 50
Models, Chemical
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
Quinones / chemistry*
Structure-Activity Relationship
Uronic Acids / chemistry

Substances

Carbohydrates
Enzyme Inhibitors
Glycosides
Quinones
Uronic Acids
Protein Tyrosine Phosphatase, Non-Receptor Type 1