Synthesis and biological evaluation of GPR40/FFAR1 agonists containing 3,5-dimethylisoxazole

Eur J Med Chem. 2016 Jun 30:116:46-58. doi: 10.1016/j.ejmech.2016.03.054. Epub 2016 Mar 25.

Abstract

GPR40 is an attractive target due to its glucose-stimulated insulin secretion effect with low risk of causing hypoglycemia, which also can be seen from the clinical studies using TAK-875 (fasiglifam). In the present studies, we discovered a series of analogues containing 3,5-dimethylisoxazole as potent GPR40 agonists, especially compound 11k with an EC50 value of 15.9 nM. Moreover, compound 11k reduced glucose excursion to 23.1% in ICR mice and 29.5% in type 2 diabetic C57BL/6 mice at 30 mg/kg. It also exhibited satisfactory PK profile. Docking studies were conducted to explain the interaction mode of this series. In summary, compound 11k with robust efficacy in vitro and in vivo is a promising drug candidate for further investigation.

Keywords: 3,5-Dimethylisoxazole; Diabetes; GPR40 agonist; Oral glucose tolerance test.

MeSH terms

  • Animals
  • Chemistry Techniques, Synthetic
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / metabolism
  • Hypoglycemic Agents / pharmacokinetics
  • Hypoglycemic Agents / pharmacology*
  • Male
  • Mice
  • Molecular Docking Simulation
  • Oxazoles / chemical synthesis*
  • Oxazoles / metabolism
  • Oxazoles / pharmacokinetics
  • Oxazoles / pharmacology*
  • Protein Conformation
  • Rats
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, G-Protein-Coupled / chemistry
  • Receptors, G-Protein-Coupled / metabolism
  • Structure-Activity Relationship

Substances

  • Ffar1 protein, mouse
  • Hypoglycemic Agents
  • Oxazoles
  • Receptors, G-Protein-Coupled