Efficient synthesis of a novel m-phenylene derivative as a selective EP4 agonist inducing follicular growth and maturation in the ovary

Bioorg Med Chem Lett. 2011 Dec 15;21(24):7505-8. doi: 10.1016/j.bmcl.2011.09.004. Epub 2011 Oct 1.

Abstract

An efficient and straightforward synthesis of a novel m-phenylene derivative has been developed. The optically pure dibromo compound was selected as a starting material. Through a protocol involving the Prins reaction and two steps of the Horner-Wadsworth-Emmons reaction, the basic skeleton was constructed with appropriate alpha and omega side chains. The compound proved to be a highly selective EP(4) agonist and a possible drug candidate for maturation of the uterine cervix.

MeSH terms

  • Animals
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Cervix Uteri / growth & development
  • Female
  • Guinea Pigs
  • Ovarian Follicle / drug effects*
  • Ovarian Follicle / growth & development
  • Rabbits
  • Receptors, Prostaglandin E, EP4 Subtype / agonists*
  • Receptors, Prostaglandin E, EP4 Subtype / metabolism

Substances

  • Benzofurans
  • Receptors, Prostaglandin E, EP4 Subtype