Small-molecule androgen receptor downregulators as an approach to treatment of advanced prostate cancer

Bioorg Med Chem Lett. 2011 Sep 15;21(18):5442-5. doi: 10.1016/j.bmcl.2011.06.122. Epub 2011 Jul 2.

Abstract

Chemical starting points were investigated for downregulation of the androgen receptor as an approach to treatment of advanced prostate cancer. Although prototypic steroidal downregulators such as 6a designed for intramuscular administration showed insufficient cellular potency, a medicinal chemistry program derived from a novel androgen receptor ligand 8a led to 6-[4-(4-cyanobenzyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (10b), for which high plasma levels following oral administration in a preclinical model compensate for moderate cellular potency.

MeSH terms

  • Dose-Response Relationship, Drug
  • Down-Regulation / drug effects
  • Humans
  • Ligands
  • Male
  • Models, Molecular
  • Molecular Structure
  • Molecular Weight
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / metabolism
  • Pyridazines / chemical synthesis
  • Pyridazines / chemistry
  • Pyridazines / pharmacology*
  • Receptors, Androgen / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Ligands
  • Pyridazines
  • Receptors, Androgen
  • pyridazine