Identification and biological evaluation of thiazole-based inverse agonists of RORγt

Bioorg Med Chem Lett. 2018 May 15;28(9):1446-1455. doi: 10.1016/j.bmcl.2018.03.093. Epub 2018 Apr 3.

Abstract

The nuclear receptor retinoic acid receptor-related orphan receptor gamma t (RORγt) is a transcription factor that drives Th17 cell differentiation and IL-17 production in both innate and adaptive immune cells. The IL-23/IL-17 pathway is implicated in major autoimmune and inflammatory diseases. RORγt lies at the core of this pathway and represents an attractive opportunity for intervention with a small molecule. Despite diverse chemical series having been reported, combining high potency and nuclear receptor selectivity with good physicochemical properties remains a challenging endeavor in the field of RORγt drug discovery. We describe the discovery and evaluation of a new class of potent and selective RORγt inverse agonists based on a thiazole core. Acid analog 1j demonstrated oral bioavailability in rats and was potent in a human whole blood assay, suggesting potential utility in treating autoimmune and inflammatory diseases such as psoriasis. X-ray crystallographic data helped to elucidate the molecular mechanism for RORγt inhibition with this series.

Keywords: Inverse agonist; RORc; RORγt; Retinoid-related orphan receptor gamma t; Thiazole.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Receptors, Retinoic Acid / agonists*
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Receptors, Retinoic Acid
  • Thiazoles