Synthesis and PPAR-gamma ligand-binding activity of the new series of 2'-hydroxychalcone and thiazolidinedione derivatives

Chem Pharm Bull (Tokyo). 2006 Mar;54(3):368-71. doi: 10.1248/cpb.54.368.

Abstract

Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-gamma (PPAR-gamma) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-gamma transactivation potential, while the others showed antagonistic activity against PPAR-gamma transactivation. Among the chalcones, compound 5 was the most potent, and structure-activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4' or 5' in chalcone plays a key role in determining the potency of PPAR-gamma activation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chalcone / analogs & derivatives*
  • Chalcone / chemistry
  • Chalcone / metabolism
  • Chalcones
  • Indicators and Reagents
  • Ligands
  • Luciferases / chemistry
  • PPAR gamma / metabolism*
  • Reverse Transcriptase Polymerase Chain Reaction
  • Structure-Activity Relationship
  • Tetrazolium Salts
  • Thiazoles
  • Thiazolidinediones / chemistry*
  • Thiazolidinediones / metabolism*
  • Transfection

Substances

  • Chalcones
  • Indicators and Reagents
  • Ligands
  • PPAR gamma
  • Tetrazolium Salts
  • Thiazoles
  • Thiazolidinediones
  • Chalcone
  • Luciferases
  • thiazolyl blue
  • 2'-hydroxychalcone