Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs). Part I

Bioorg Med Chem. 2015 May 15;23(10):2568-78. doi: 10.1016/j.bmc.2015.03.032. Epub 2015 Mar 19.

Abstract

To develop effective drugs for hypogonadism, sarcopenia, and cachexia, we designed, synthesized, and evaluated selective androgen receptor modulators (SARMs) that exhibit not only anabolic effects on organs such as muscles and the central nervous system (CNS) but also neutral or antagonistic effects on the prostate. Based on the information obtained from a docking model with androgen receptor (AR), we modified a hit compound A identified through high-throughput screening. Among the prepared compounds, 1-(4-cyano-1-naphthyl)-2,3-disubstituted pyrrolidine derivatives 17h, 17m, and 17j had highly potent AR agonistic activities in vitro and good tissue selectivity in vivo. These derivatives increased the weight of the levator ani muscle without influencing the prostate and seminal vesicle. In addition, these compounds induced sexual behavior in castrated rats, indicating that the compounds could also act as agonists on the CNS.

Keywords: AR; Androgen receptor; Selective androgen receptor modulators (SARMs); Testosterone.

MeSH terms

  • Anabolic Agents / chemical synthesis*
  • Anabolic Agents / pharmacology
  • Androgens / chemical synthesis*
  • Androgens / pharmacology
  • Animals
  • Castration
  • Central Nervous System / drug effects
  • Central Nervous System / metabolism
  • Gene Expression
  • Humans
  • Male
  • Molecular Docking Simulation
  • Muscle, Skeletal / drug effects
  • Muscle, Skeletal / metabolism
  • Naphthols / chemical synthesis*
  • Naphthols / pharmacology
  • Prostate / drug effects
  • Prostate / metabolism
  • Protein Binding
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Androgen / genetics
  • Receptors, Androgen / metabolism*
  • Sexual Behavior, Animal / drug effects
  • Structure-Activity Relationship
  • Testosterone / pharmacology

Substances

  • Anabolic Agents
  • Androgens
  • Naphthols
  • Pyrrolidines
  • Receptors, Androgen
  • Testosterone