Novel retinoidal tropolone derivatives. Bioisosteric relationship of tropolone ring with benzoic acid moiety in retinoid structure

Chem Pharm Bull (Tokyo). 2001 Apr;49(4):501-3. doi: 10.1248/cpb.49.501.


Several tropolone derivatives (4-7) were designed as novel retinoids on the assumption that the tropolone ring may mimic the benzoic acid moiety in retinoid structures, such as Am80 (2). Among the synthesized compounds, 5-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethynyl]tropolone (7a) showed moderate potency as a differentiation-inducer of HL-60 cells. The activities of the tropolones were greatly enhanced in the presence of HX630, an RXR agonist (retinoid synergist).

MeSH terms

  • Benzoates / chemistry*
  • Cell Differentiation / drug effects
  • Drug Synergism
  • HL-60 Cells
  • Humans
  • Isomerism
  • Receptors, Retinoic Acid / drug effects
  • Retinoid X Receptors
  • Retinoids / chemistry*
  • Transcription Factors / drug effects
  • Tropolone / chemistry*


  • Benzoates
  • Receptors, Retinoic Acid
  • Retinoid X Receptors
  • Retinoids
  • Transcription Factors
  • Tropolone