Structure-Based Approach To Identify 5-[4-Hydroxyphenyl]pyrrole-2-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

J Med Chem. 2017 Jul 27;60(14):6451-6457. doi: 10.1021/acs.jmedchem.7b00373. Epub 2017 Jul 11.

Abstract

In an effort to find new and safer treatments for osteoporosis and frailty, we describe a novel series of selective androgen receptor modulators (SARMs). Using a structure-based approach, we identified compound 7, a potent AR (ARE EC50 = 0.34 nM) and selective (N/C interaction EC50 = 1206 nM) modulator. In vivo data, an AR LBD X-ray structure of 7, and further insights from modeling studies of ligand receptor interactions are also presented.

MeSH terms

  • Anabolic Agents / chemical synthesis
  • Anabolic Agents / chemistry*
  • Anabolic Agents / pharmacokinetics
  • Anabolic Agents / pharmacology
  • Androgens / chemical synthesis
  • Androgens / chemistry*
  • Androgens / pharmacokinetics
  • Androgens / pharmacology
  • Animals
  • Crystallography, X-Ray
  • Hypothalamo-Hypophyseal System / drug effects
  • Male
  • Molecular Docking Simulation
  • Muscle, Skeletal / drug effects
  • Muscle, Skeletal / physiology
  • Nitriles / chemical synthesis
  • Nitriles / chemistry*
  • Nitriles / pharmacology
  • Organ Size / drug effects
  • Organ Specificity
  • Prostate / drug effects
  • Prostate / physiology
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Pyrroles / pharmacokinetics
  • Pyrroles / pharmacology
  • Rats
  • Receptors, Androgen / metabolism*
  • Seminal Vesicles / drug effects
  • Seminal Vesicles / physiology
  • Structure-Activity Relationship

Substances

  • 5-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrrole-2-carbonitrile
  • Anabolic Agents
  • Androgens
  • Nitriles
  • Pyrroles
  • Receptors, Androgen