Synthesis of dihydroimidazole tethered imidazolinethiones and their activity as novel antagonists of the nuclear retinoic acid receptor-related orphan receptors (RORs)

Bioorg Med Chem Lett. 2017 Apr 1;27(7):1608-1610. doi: 10.1016/j.bmcl.2017.02.014. Epub 2017 Feb 10.

Abstract

Targeting the transcriptional activity of nuclear hormone receptors has proven an effective strategy to treat certain human diseases, and they have become a major focus point to develop novel therapies for the treatment of cancer, inflammation, autoimmune diseases, metabolic disorders, and others. One family of nuclear receptors that has attracted most interest in recent years is the retinoic acid receptor-related orphan receptors (RORs), in particular RORγ. RORγ is a critical regulator of the immune system and RORγ antagonists have shown activity in animal models of inflammatory autoimmune diseases. Here we present the synthesis and biological evaluation of dihydroimidazole tethered imidazolinethiones. We have identified several dual RORγ/α and pan-ROR antagonists with significant activity in cellular assays that could serve as starting points for future optimization efforts to generate potent and selective RORγ modulators.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Cricetulus
  • Imidazolines / chemical synthesis
  • Imidazolines / pharmacology*
  • Nuclear Receptor Subfamily 1, Group F, Member 1 / antagonists & inhibitors
  • Nuclear Receptor Subfamily 1, Group F, Member 2 / antagonists & inhibitors
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / antagonists & inhibitors
  • Orphan Nuclear Receptors / antagonists & inhibitors*
  • Thiones / chemical synthesis
  • Thiones / pharmacology*

Substances

  • Imidazolines
  • Nuclear Receptor Subfamily 1, Group F, Member 1
  • Nuclear Receptor Subfamily 1, Group F, Member 2
  • Nuclear Receptor Subfamily 1, Group F, Member 3
  • Orphan Nuclear Receptors
  • Thiones