Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt

Bioorg Med Chem Lett. 2014 Nov 15;24(22):5265-7. doi: 10.1016/j.bmcl.2014.09.053. Epub 2014 Sep 28.

Abstract

Retinoic acid receptor-related orphan nuclear receptor gamma t (RORγt) is a key transcription factor for the development of Th17 cells. Inhibiting RORγt activity is thought to be beneficial in targeting a variety of inflammatory and autoimmune disorders. Recently N-(5-(arylcarbonyl)thiazol-2-yl)amides were described as RORγt antagonists with in vivo efficacy in experimental autoimmune encephalomyelitis (EAE) and collagen-induced arthritis (CIA) via oral administration. So far no selective small molecule ligands have been revealed for RORβ. We show, that one compound of this class, namely N-[5-(2-chloro-benzoyl)-4-(3-chlorophenyl)-thiazol-2-yl]-2-(4-ethanesulfonyl-phenyl)-acetamide (4) is a potent dual inverse agonist towards RORγt and RORβ devoid of activity to 18 other human nuclear receptors and thus can serve as chemical probe to deepen our understanding about RORβ and its biology.

Keywords: 2-Aminothiazole; RORβ; RORγt; Retinoid-related orphan receptor beta; Retinoid-related orphan receptor gamma t.

MeSH terms

  • Benzeneacetamides / chemistry*
  • Benzeneacetamides / metabolism
  • Drug Inverse Agonism
  • Fluorescence Resonance Energy Transfer
  • Humans
  • Ligands
  • Nuclear Receptor Subfamily 1, Group F, Member 2 / agonists*
  • Nuclear Receptor Subfamily 1, Group F, Member 2 / metabolism
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / agonists*
  • Nuclear Receptor Subfamily 1, Group F, Member 3 / metabolism
  • Protein Binding
  • Th17 Cells / immunology
  • Th17 Cells / metabolism
  • Thiazoles / chemistry*
  • Thiazoles / metabolism
  • Tretinoin / chemistry*
  • Tretinoin / metabolism

Substances

  • Benzeneacetamides
  • Ligands
  • N-(5-(2-chlorobenzoyl)-4-(3-chlorophenyl)thiazol-2-yl)-2-(4-ethanesulfonylphenyl)acetamide
  • Nuclear Receptor Subfamily 1, Group F, Member 2
  • Nuclear Receptor Subfamily 1, Group F, Member 3
  • Thiazoles
  • Tretinoin