Design, synthesis, and evaluation of a series of novel phenylpropanoic acid derivatives agonists for the FFA1

Chem Biol Drug Des. 2019 May;93(5):900-909. doi: 10.1111/cbdd.13480. Epub 2019 Jan 29.

Abstract

Free fatty acid 1 (FFA1/GPR40) has attracted extensive attention as a novel target for the treatment of type 2 diabetes for its role in the enhancement of insulin secretion with glucose dependency. Aiming to develop novel potent FFA1 agonists, a new series of phenylpropionic acid derivatives were designed and synthesized on the basis of the modification of chemical cement of TAK-875, AMG-837, and LY2881835. Among them, most promising compounds 7, 14, and 15 were obtained with EC50 values of 82, 79, and 88 nM, exhibiting a powerful agonistic activity compared to TAK-875 (95.1 nM). During Oral glucose tolerance test in normal mice, compound 7, 14, and 15 had significant glucose-lowering effect at the dose of 50 mg/kg. Furthermore, compound 15 (50 mg/kg) also significantly improved in glucose tolerance in type 2 diabetic mice. Herein, we reported the discovery and optimization of a series of potent FFA1 agonists. The discovery supported further exploration surrounding this scaffold.

Keywords: FFA1; agonistic activity; synthesis; type 2 diabetes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood Glucose / analysis
  • Diabetes Mellitus, Experimental / drug therapy
  • Drug Design*
  • Glucose Tolerance Test
  • Humans
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / therapeutic use
  • Ligands
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Mice, Inbred ICR
  • Propionates / chemistry*
  • Propionates / therapeutic use
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, G-Protein-Coupled / genetics
  • Receptors, G-Protein-Coupled / metabolism

Substances

  • Blood Glucose
  • FFAR1 protein, human
  • Hypoglycemic Agents
  • Ligands
  • Propionates
  • Receptors, G-Protein-Coupled