Potent, nonsteroidal selective androgen receptor modulators (SARMs) based on 8H-[1,4]oxazino[2,3-f]quinolin-8-ones

Bioorg Med Chem Lett. 2007 Oct 1;17(19):5442-6. doi: 10.1016/j.bmcl.2007.07.034. Epub 2007 Jul 25.

Abstract

A series of androgen receptor modulators based on 8H-[1,4]oxazino[2,3-f]quinolin-8-ones was synthesized and evaluated in an androgen receptor transcriptional activation assay. The most potent analogues from the series exhibited single-digit nanomolar potency in vitro. Compound 18h demonstrated full efficacy in the maintenance of muscle weight, at 10 mg/kg, with reduced activity in prostate weight in an in vivo model of androgen action.

MeSH terms

  • Animals
  • Cell Line
  • Dose-Response Relationship, Drug
  • Humans
  • Indicators and Reagents
  • Male
  • Models, Molecular
  • Orchiectomy
  • Oxazines / chemical synthesis*
  • Oxazines / pharmacology*
  • Quinolones / chemical synthesis*
  • Quinolones / pharmacology*
  • Rats
  • Receptors, Androgen / chemistry
  • Receptors, Androgen / drug effects*
  • Receptors, Progesterone / chemistry
  • Receptors, Progesterone / drug effects
  • Receptors, Somatotropin / chemistry
  • Receptors, Somatotropin / drug effects
  • Structure-Activity Relationship
  • Testosterone / blood

Substances

  • Indicators and Reagents
  • Oxazines
  • Quinolones
  • Receptors, Androgen
  • Receptors, Progesterone
  • Receptors, Somatotropin
  • Testosterone