Nonsteroidal androgen receptor agonists based on 4-(trifluoromethyl)-2H-pyrano[3,2-g]quinolin-2-one

Bioorg Med Chem Lett. 1999 Apr 5;9(7):1003-8. doi: 10.1016/s0960-894x(99)00118-3.


A series of 2H-pyrano[3,2-g]quinolin-2-ones was prepared and tested for the ability to modulate the transcriptional activity of the human androgen receptor (hAR). The parent compound, 4-(trifluoromethyl)-2H-pyrano[3,2-g]quinolin-2-one, displayed moderate interaction with hAR, but substituted analogues were potent hAR modulators in vitro as measured by an hAR cotransfection assay in CV-1 cells and bound to hAR with high affinity in a whole cell assay. Several analogues were able to activate hAR-mediated gene transcription more potently and efficaciously than dihydrotestosterone.

MeSH terms

  • Androgens*
  • Animals
  • Benzopyrans / chemistry*
  • Benzopyrans / pharmacology*
  • COS Cells
  • Cell Line
  • Humans
  • Quinolones / chemistry*
  • Quinolones / pharmacology*
  • Receptors, Androgen / genetics
  • Receptors, Androgen / metabolism
  • Structure-Activity Relationship
  • Transcription, Genetic / drug effects
  • Transfection


  • Androgens
  • Benzopyrans
  • Quinolones
  • Receptors, Androgen