Discovery of a novel class of 1,3-dioxane-2-carboxylic acid derivatives as subtype-selective peroxisome proliferator-activated receptor alpha (PPARalpha) agonists

Bioorg Med Chem Lett. 2008 Mar 15;18(6):2128-32. doi: 10.1016/j.bmcl.2008.01.086. Epub 2008 Jan 30.

Abstract

A new series of 1,3-dioxane-2-carboxylic acid derivatives was synthesized and evaluated for agonist activity at human peroxisome proliferator-activated receptor (PPAR) subtypes. Structure-activity relationship studies led to the identification of 2-methyl-c-5-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)butyl]-1,3-dioxane-r-2-carboxylic acid 4b as a potent PPARalpha agonist with high subtype selectivity at human receptor subtypes. This compound exhibited a substantial hypolipidemic effect in type 2 diabetic KK-A(y) mice.

MeSH terms

  • Animals
  • Blood Glucose / metabolism
  • Diabetes Mellitus, Type 2 / drug therapy*
  • Dioxanes / chemical synthesis*
  • Dioxanes / pharmacology*
  • Disease Models, Animal
  • Humans
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / pharmacology
  • Hypolipidemic Agents / chemical synthesis
  • Hypolipidemic Agents / pharmacology
  • Lipoproteins / blood
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mice, Inbred Strains
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / pharmacology*
  • PPAR alpha / agonists*
  • Structure-Activity Relationship
  • Triglycerides / blood

Substances

  • 2-methyl-c-5-(4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)butyl)-1,3-dioxane-r-2-carboxylic acid
  • Blood Glucose
  • Dioxanes
  • Hypoglycemic Agents
  • Hypolipidemic Agents
  • Lipoproteins
  • Oxazoles
  • PPAR alpha
  • Triglycerides