Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase

Jun Chen; Jun Liu; Luyong Zhang; Guanzhong Wu; Weiyi Hua; Xiaoming Wu; Hongbin Sun

doi:10.1016/j.bmcl.2006.03.009

Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase

Bioorg Med Chem Lett. 2006 Jun 1;16(11):2915-9. doi: 10.1016/j.bmcl.2006.03.009. Epub 2006 Mar 20.

Authors

Jun Chen¹, Jun Liu, Luyong Zhang, Guanzhong Wu, Weiyi Hua, Xiaoming Wu, Hongbin Sun

Affiliation

¹ Center for Drug Discovery, College of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China.

PMID: 16546381
DOI: 10.1016/j.bmcl.2006.03.009

Abstract

Oleanolic acid and its synthetic derivatives have been identified as novel inhibitors of glycogen phosphorylase. Within this series of compounds, 4 (IC50 = 3.3 microM) is the most potent GPa inhibitor. Preliminary structure-activity relationships of the oleanolic acid derivatives are discussed.

Publication types

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

MeSH terms

Animals
Blood Glucose / metabolism
Cyclization
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / metabolism*
Glycogen Phosphorylase / antagonists & inhibitors*
Glycogen Phosphorylase / metabolism*
Hyperglycemia / blood
Mice
Molecular Structure
Muscles / drug effects
Muscles / enzymology
Oleanolic Acid / analogs & derivatives*
Oleanolic Acid / chemistry
Rabbits
Structure-Activity Relationship
Triterpenes / chemical synthesis
Triterpenes / chemistry*
Triterpenes / pharmacology*

Substances

Blood Glucose
Enzyme Inhibitors
Triterpenes
Oleanolic Acid
Glycogen Phosphorylase