Syntheses and evaluation of naphthalenyl- and chromenyl-pyrrolyl-benzoic acids as potent and selective retinoic acid receptor alpha agonists

Bioorg Med Chem Lett. 2000 Apr 3;10(7):623-5. doi: 10.1016/s0960-894x(00)00067-6.

Abstract

Synthesis and structure activity relationships (SAR) of RAR alpha-selective agonists are discussed. 4-[5-(5,8-Dimethyl-2H-3-chromenyl)-1H-2-pyrrolyl]benzoic acid (12a), which possesses a flat structural moiety and an oxygen atom at the hydrophobic part, showed highly selective transactivation activity at the RAR alpha receptor.

MeSH terms

  • Benzoates / chemical synthesis*
  • Benzoates / pharmacology
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / pharmacology
  • Cell Differentiation / drug effects
  • HL-60 Cells
  • Humans
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / pharmacology
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology
  • Receptors, Retinoic Acid / agonists*
  • Retinoic Acid Receptor alpha
  • Structure-Activity Relationship

Substances

  • Benzoates
  • Benzopyrans
  • Naphthalenes
  • Pyrroles
  • RARA protein, human
  • Receptors, Retinoic Acid
  • Retinoic Acid Receptor alpha