Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase

Journal of Natural Products
2008.0

Abstract

Bredemolic acid (3) is a naturally occurring 2β,3α-isomer of maslinic acid (1) that is an allosteric site inhibitor of glycogen phosphorylase (GP). A practical synthesis of 3 was accomplished (18% yield) in five steps starting from the readily available 2β,3β-diol 6a. In a similar fashion, 2β,3α-dihydroxyurs-12-en-28-oic acid (4) was synthesized as a natural 2β,3α-isomer of corosolic acid (2). Compounds 3 and 4 exhibited significant inhibitory activity against rabbit muscle GPa with IC(50) values of 6.25 and 1.1 μM, respectively.

Knowledge Graph

Similar Paper

Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase
Journal of Natural Products 2008.0
Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases
Bioorganic & Medicinal Chemistry Letters 2005.0
Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors
Bioorganic & Medicinal Chemistry Letters 2006.0
Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases
Bioorganic & Medicinal Chemistry Letters 2007.0
Synthesis of 3-Deoxypentacyclic Triterpene Derivatives as Inhibitors of Glycogen Phosphorylase
Journal of Natural Products 2009.0
Terpenoids. III: Synthesis and biological evaluation of 23-hydroxybetulinic acid derivatives as novel inhibitors of glycogen phosphorylase
Bioorganic & Medicinal Chemistry Letters 2009.0
Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase
Bioorganic & Medicinal Chemistry Letters 2006.0
Naturally Occurring Pentacyclic Triterpenes as Inhibitors of Glycogen Phosphorylase: Synthesis, Structure−Activity Relationships, and X-ray Crystallographic Studies
Journal of Medicinal Chemistry 2008.0
Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 2008.0
Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases
Bioorganic & Medicinal Chemistry 2008.0