Efficient Synthesis of a Multi-Substituted Diphenylmethane Skeleton as a Steroid Mimetic

Bioorg Med Chem Lett. 2017 Jun 1;27(11):2590-2593. doi: 10.1016/j.bmcl.2017.03.066. Epub 2017 Mar 24.

Abstract

Steroids are important components of cell membranes and are involved in several physiological functions. A diphenylmethane (DPM) skeleton has recently been suggested to act as a mimetic of the steroid skeleton. However, difficulties are associated with efficiently introducing different substituents between two phenyl rings of the DPM skeleton, and, thus, further structural development based on the DPM skeleton has been limited. We herein developed an efficient synthetic method for introducing different substituents into two phenyl rings of the DPM skeleton. We also synthesized DPM-based estrogen receptor (ER) modulators using our synthetic method and evaluated their ER transcriptional activities.

Keywords: Anti-estrogenic activity; Diphenylmethane skeleton; Multi-substituted.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzhydryl Compounds / chemical synthesis
  • Benzhydryl Compounds / chemistry*
  • Benzhydryl Compounds / metabolism
  • Estrogen Receptor alpha / antagonists & inhibitors
  • Estrogen Receptor alpha / metabolism
  • HEK293 Cells
  • Humans
  • Inhibitory Concentration 50
  • Receptors, Estrogen / antagonists & inhibitors
  • Receptors, Estrogen / metabolism*
  • Selective Estrogen Receptor Modulators / chemical synthesis
  • Selective Estrogen Receptor Modulators / chemistry
  • Selective Estrogen Receptor Modulators / metabolism
  • Steroids / chemical synthesis
  • Steroids / chemistry*
  • Steroids / metabolism
  • Structure-Activity Relationship

Substances

  • Benzhydryl Compounds
  • Estrogen Receptor alpha
  • Receptors, Estrogen
  • Selective Estrogen Receptor Modulators
  • Steroids
  • diphenylmethane