Synthesis and structure-activity relationships of 3-phenyl-2-propenamides as inhibitors of glycogen phosphorylase a

Bioorg Med Chem Lett. 2006 Nov 15;16(22):5892-6. doi: 10.1016/j.bmcl.2006.08.055. Epub 2006 Aug 30.

Abstract

A series of 3-phenyl-2-propenamides discovered from a high-throughput screening campaign as novel, potent, glucose-sensitive inhibitors of human liver glycogen phosphorylase a is described. A solid-phase synthesis on DMHB resin was also developed which provided efficient access not only to certain analogues that could not be cleanly made using more traditional means, but also to a variety of additional analogues. The SAR scope and synthetic strategy are presented herein.

MeSH terms

  • Acrylamides / chemical synthesis*
  • Acrylamides / pharmacology*
  • Combinatorial Chemistry Techniques
  • Drug Design
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Glycogen Phosphorylase / antagonists & inhibitors*
  • Humans
  • Liver / enzymology
  • Resins, Synthetic / chemistry
  • Structure-Activity Relationship

Substances

  • Acrylamides
  • Enzyme Inhibitors
  • Resins, Synthetic
  • Glycogen Phosphorylase