Synthesis and evaluation of anilinohexafluoroisopropanols as activators/modulators of LXRalpha and beta

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5231-7. doi: 10.1016/j.bmcl.2006.06.081. Epub 2006 Jul 31.

Abstract

A series of branched and unbranched anilinohexafluoroisopropanols related to the known sulfonamide T0901317 were prepared and evaluated as activators/modulators of both LXRalpha and LXRbeta. A structure-activity relationship was established and compounds with high potency on both the receptors were identified. Many compounds showed a tendency toward selectivity for LXRbeta versus LXRalpha. Several analogues were evaluated for effects on plasma lipoprotein levels in mice. A few of these significantly raised HDL-cholesterol levels in plasma but showed markedly different effects on liver triglyceride content, suggesting that this series may yield candidates with improved efficacy/safety profiles compared to existing molecules.

MeSH terms

  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / pharmacokinetics
  • Aniline Compounds / pharmacology
  • Animals
  • Atherosclerosis / drug therapy
  • Cholesterol, HDL / blood
  • DNA-Binding Proteins / drug effects*
  • Lipoproteins / blood
  • Liver
  • Liver X Receptors
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Orphan Nuclear Receptors
  • Propanols / chemical synthesis
  • Propanols / pharmacokinetics
  • Propanols / pharmacology
  • Receptors, Cytoplasmic and Nuclear / drug effects*
  • Structure-Activity Relationship
  • Transcriptional Activation / drug effects
  • Triglycerides / blood

Substances

  • Aniline Compounds
  • Cholesterol, HDL
  • DNA-Binding Proteins
  • Lipoproteins
  • Liver X Receptors
  • Nr1h3 protein, mouse
  • Orphan Nuclear Receptors
  • Propanols
  • Receptors, Cytoplasmic and Nuclear
  • Triglycerides