SAR studies of 3-arylpropionic acids as potent and selective agonists of sphingosine-1-phosphate receptor-1 (S1P1) with enhanced pharmacokinetic properties

Bioorg Med Chem Lett. 2007 Feb 1;17(3):828-31. doi: 10.1016/j.bmcl.2006.10.057. Epub 2006 Oct 25.

Abstract

Structure-activity relationship (SAR) studies of 3-arylpropionic acids-a class of novel S1P(1) selective agonists-by introducing substitution to the propionic acid chain and replacing the adjacent phenyl ring with pyridine led to a series of modified 3-arylpropionic acids with enhanced half-life in rat. These analogs (e.g., cyclopropanecarboxylic acids) exhibited longer half-life in rat than did unmodified 3-arylpropionic acids. This result suggests that metabolic oxidation at the propionic acid chain, particularly at the C3 benzylic position of 3-arylpropionic acids, is probably responsible for their short half-life in rodent.

MeSH terms

  • Animals
  • Biological Availability
  • CHO Cells
  • Cricetinae
  • Cricetulus
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Half-Life
  • Lymphocyte Count
  • Lymphocytes / drug effects
  • Lymphocytes / metabolism
  • Male
  • Mice
  • Propionates / chemical synthesis*
  • Propionates / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Lysosphingolipid / agonists*
  • Structure-Activity Relationship

Substances

  • Propionates
  • Receptors, Lysosphingolipid
  • Guanosine 5'-O-(3-Thiotriphosphate)