Liver X receptor agonists with selectivity for LXRbeta; N-aryl-3,3,3-trifluoro-2-hydroxy-2-methylpropionamides

Bioorg Med Chem Lett. 2009 Apr 1;19(7):2009-12. doi: 10.1016/j.bmcl.2009.02.039. Epub 2009 Feb 13.

Abstract

The synthesis and SAR of a new series of LXR agonist is reported. The N-Aryl-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide hits were found in a limited screen of the AstraZeneca compound collection. The effort to optimize these hits into LXRbeta selectivity is described. Compound 20 displayed desirable pharmacokinetic profile and up regulation of ABCA1 and ABCG1 mRNA in the brain were achieved when evaluated in vivo in mice.

MeSH terms

  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters / metabolism
  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / pharmacology*
  • Animals
  • Brain / metabolism
  • Cell Line
  • Computer Simulation
  • DNA-Binding Proteins / agonists*
  • DNA-Binding Proteins / metabolism
  • Genes, Reporter
  • Humans
  • Lactates / chemical synthesis
  • Lactates / chemistry
  • Lactates / pharmacology*
  • Liver X Receptors
  • Mice
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • Up-Regulation

Substances

  • ABCA1 protein, human
  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters
  • Amides
  • DNA-Binding Proteins
  • Lactates
  • Liver X Receptors
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear
  • Sulfonamides