Design, synthesis, and evaluation of potent, structurally novel peroxisome proliferator-activated receptor (PPAR) delta-selective agonists

Bioorg Med Chem. 2007 Aug 1;15(15):5177-90. doi: 10.1016/j.bmc.2007.05.023. Epub 2007 May 13.

Abstract

A series of 3-(4-alkoxyphenyl)propanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) delta-selective agonists, based on our previously discovered potent human PPARalpha/delta dual agonist TIPP-401 as a lead compound. Structure-activity relationship studies clearly indicated the importance of the chain length of the alkoxy group at the 4-position, and the n-butoxy compound exhibited the most potent PPARdelta transactivation activity and highest PPARdelta selectivity. The (S)-enantiomer of a representative compound exhibited extremely potent PPARdelta transactivation activity, comparable with or somewhat superior to that of the known PPARdelta-selective agonist, GW-501516. The representative compound regulated the expression of genes involved in lipid and glucose homeostasis, and should be useful not only as a chemical tool to study PPARdelta function, but also as a candidate drug for the treatment of metabolic syndrome.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Butyrates / chemistry
  • Butyrates / pharmacology*
  • Cell Line
  • Eicosapentaenoic Acid / pharmacology
  • Humans
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / pharmacology*
  • Male
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Mutagenicity Tests
  • PPAR delta / agonists*
  • Phenoxyacetates / pharmacology
  • Phenylurea Compounds / pharmacology
  • Thiazoles / pharmacology

Substances

  • 4-(3-(2-propyl-3-hydroxy-4-acetyl)phenoxy)propyloxyphenoxy acetic acid
  • Butyrates
  • GW 2433
  • GW 501516
  • Hydrocarbons, Fluorinated
  • KCL compound
  • PPAR delta
  • Phenoxyacetates
  • Phenylurea Compounds
  • TIPP-401
  • Thiazoles
  • Eicosapentaenoic Acid