Discovery and Structure-Activity Relationship (SAR) of a Series of Ethanolamine-Based Direct-Acting Agonists of Sphingosine-1-phosphate (S1P1)

J Med Chem. 2016 Jul 14;59(13):6248-64. doi: 10.1021/acs.jmedchem.6b00373. Epub 2016 Jul 1.

Abstract

Sphingosine-1-phosphate (S1P) is a bioactive sphingolipid metabolite that regulates a multitude of physiological processes such as lymphocyte trafficking, cardiac function, vascular development, and inflammation. Because of the ability of S1P1 receptor agonists to suppress lymphocyte egress, they have great potential as therapeutic agents in a variety of autoimmune diseases. In this article, the discovery of selective, direct acting S1P1 agonists utilizing an ethanolamine scaffold containing a terminal carboxylic acid is described. Potent S1P1 agonists such as compounds 18a and 19a which have greater than 1000-fold selectivity over S1P3 are described. These compounds efficiently reduce blood lymphocyte counts in rats through 24 h after single doses of 1 and 0.3 mpk, respectively. Pharmacodynamic properties of both compounds are discussed. Compound 19a was further studied in two preclinical models of disease, exhibiting good efficacy in both the rat adjuvant arthritis model (AA) and the mouse experimental autoimmune encephalomyelitis model (EAE).

MeSH terms

  • Animals
  • Arthritis / drug therapy
  • Dogs
  • Encephalomyelitis, Autoimmune, Experimental / drug therapy
  • Ethanolamine / chemistry*
  • Ethanolamine / pharmacokinetics
  • Ethanolamine / pharmacology*
  • Ethanolamine / therapeutic use
  • Female
  • Haplorhini
  • Humans
  • Lymphocyte Count
  • Lymphocytes / cytology
  • Lymphocytes / drug effects*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Rats
  • Rats, Inbred Lew
  • Receptors, Lysosphingolipid / agonists*
  • Receptors, Lysosphingolipid / metabolism
  • Structure-Activity Relationship

Substances

  • Receptors, Lysosphingolipid
  • Ethanolamine