2-Aryl-N-acyl indole derivatives as liver X receptor (LXR) agonists

Bioorg Med Chem Lett. 2007 Aug 15;17(16):4442-6. doi: 10.1016/j.bmcl.2007.06.017. Epub 2007 Jun 10.

Abstract

Structure-activity relationship studies on a series of Boc-indole derivatives as LXR agonists are described. Compound 1 was identified as an LXR agonist through structure-based virtual screening followed by high-throughput gene profiling. Replacement of the indan linker portion in 1 with an open-chain linker resulted in compounds with similar or improved in vitro potency and cellular functional activity. The Boc group at the N-1 position of the indole moiety can be replaced with a benzoyl group. The SAR studies led to the identification of compound 8, a potent LXRbeta agonist with an EC50 of 12 nM in the cofactor recruitment assay.

MeSH terms

  • Binding Sites
  • Cell Line
  • DNA-Binding Proteins / agonists*
  • Hepatocytes / drug effects
  • Hepatocytes / metabolism
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Liver X Receptors
  • Models, Molecular
  • Molecular Structure
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Sterol Regulatory Element Binding Protein 1 / genetics
  • Sterol Regulatory Element Binding Protein 1 / metabolism
  • Structure-Activity Relationship
  • Up-Regulation

Substances

  • DNA-Binding Proteins
  • Indoles
  • Liver X Receptors
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear
  • Sterol Regulatory Element Binding Protein 1