Synthesis of new α-glucosidase inhibitors based on oleanolic acid incorporating cinnamic amides

Chem Pharm Bull (Tokyo). 2011;59(8):1051-6. doi: 10.1248/cpb.59.1051.

Abstract

A series of α-glucosidase inhibitors with the oleanolic acid core and different cinnamic amide ligands were designed and synthesized. Their preliminary structure-activity relationships were analyzed. In general, the compounds with 3,28-disubstituted oleanolic acid exhibited stronger activity than those 28-monosubstituted analogues, and variation of cinnamic amide substitution significantly affected α-glucosidase inhibition activities. Most of the compounds showed potent inhibitory activity against α-glucosidase with much greater efficacy than a typical α-glucosidase inhibitor, acarbose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology
  • Cinnamates / chemistry*
  • Cinnamates / pharmacology*
  • Diabetes Mellitus, Type 2 / drug therapy
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Humans
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • Ligands
  • Oleanolic Acid / chemistry*
  • Oleanolic Acid / pharmacology*
  • Structure-Activity Relationship
  • alpha-Glucosidases / metabolism

Substances

  • Amides
  • Cinnamates
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Ligands
  • cinnamic acid
  • Oleanolic Acid
  • alpha-Glucosidases