Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist

Bioorg Med Chem Lett. 2004 Jun 7;14(11):2735-40. doi: 10.1016/j.bmcl.2004.03.076.

Abstract

A recently reported dual LPA1/LPA3 receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA1-selective (14b) and LPA3-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a Ki value of 18 nM at the LPA1 receptor and is significantly more potent than 1 at the LPA3 receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acylation
  • Cell Line
  • Cross-Linking Reagents / chemistry
  • Dose-Response Relationship, Drug
  • Ethanolamines / chemical synthesis
  • Ethanolamines / pharmacology
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Humans
  • Inhibitory Concentration 50
  • Ligands
  • Lipids / chemistry
  • Protein Binding
  • Receptors, Lysophosphatidic Acid / antagonists & inhibitors*
  • Receptors, Lysophosphatidic Acid / genetics
  • Structure-Activity Relationship
  • Transfection

Substances

  • Cross-Linking Reagents
  • Ethanolamines
  • Ligands
  • Lipids
  • Receptors, Lysophosphatidic Acid
  • Guanosine 5'-O-(3-Thiotriphosphate)
  • phosphorylethanolamine