Synthesis and evaluation of γ-lactam analogs of PGE₂ as EP4 and EP2/EP4 agonists

Bioorg Med Chem. 2012 Jun 1;20(11):3502-22. doi: 10.1016/j.bmc.2012.04.008. Epub 2012 Apr 11.

Abstract

To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl ω-chain moiety of the γ-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented.

MeSH terms

  • Administration, Topical
  • Animals
  • Blood Pressure / drug effects
  • CHO Cells
  • Cricetinae
  • Delayed-Action Preparations / administration & dosage
  • Delayed-Action Preparations / chemistry
  • Dinoprostone / chemistry
  • Drug Evaluation, Preclinical / methods
  • Fracture Healing / drug effects
  • Heart Rate / drug effects
  • Lactams / administration & dosage
  • Lactams / chemical synthesis*
  • Lactams / pharmacology*
  • Male
  • Mice
  • Microspheres
  • Molecular Structure
  • Polyglactin 910 / administration & dosage
  • Polyglactin 910 / chemistry
  • Prostaglandins E, Synthetic / chemical synthesis*
  • Prostaglandins E, Synthetic / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Prostaglandin E, EP2 Subtype / agonists*
  • Receptors, Prostaglandin E, EP4 Subtype / agonists*
  • Structure-Activity Relationship
  • Thiazolidines / chemistry

Substances

  • 2-mercaptothiazole-4-carboxylic acid
  • Delayed-Action Preparations
  • Lactams
  • Prostaglandins E, Synthetic
  • Receptors, Prostaglandin E, EP2 Subtype
  • Receptors, Prostaglandin E, EP4 Subtype
  • Thiazolidines
  • Polyglactin 910
  • Dinoprostone