Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands

J Med Chem. 2009 Mar 26;52(6):1540-5. doi: 10.1021/jm801532e.

Abstract

We recently discovered the isoform selective RAR beta 2 ligand 4'-octyl-4-biphenylcarboxylic acid (3, AC-55649). Although 3 is highly potent at RAR beta 2 and displays excellent selectivity, solubility issues make it unsuitable for drug development. Herein we describe the exploration of the SAR in a biphenyl and a phenylthiazole series of analogues of 3. This ultimately led to the design of 28, a novel, orally available ligand with excellent isoform selectivity for the RAR beta 2.

MeSH terms

  • Cell Line, Tumor
  • Drug Design*
  • Humans
  • Ligands
  • Receptors, Retinoic Acid / drug effects*
  • Receptors, Retinoic Acid / metabolism
  • Structure-Activity Relationship

Substances

  • Ligands
  • Receptors, Retinoic Acid
  • retinoic acid receptor beta