Estrogen receptor dependent inhibitors of NF-kappaB transcriptional activation-1 synthesis and biological evaluation of substituted 2-cyanopropanoic acid derivatives: pathway selective inhibitors of NF-kappaB, a potential treatment for rheumatoid arthritis

J Med Chem. 2007 Nov 1;50(22):5245-8. doi: 10.1021/jm701013k. Epub 2007 Sep 29.

Abstract

Pathway selective ligands of the estrogen receptor inhibit transcriptional activation of proinflammatory genes mediated by NF-kappaB. Substituted 2-cyanopropanoic acid derivatives were developed leading to the discovery of WAY-204688, an orally active, pathway selective, estrogen receptor dependent anti-inflammatory agent. This propanamide was shown to be orally active in preclinical models of inflammatory diseases, such as rheumatoid arthritis, without the proliferative effect associated with traditional estrogens.

MeSH terms

  • Administration, Oral
  • Animals
  • Animals, Genetically Modified
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Antirheumatic Agents / chemical synthesis*
  • Antirheumatic Agents / chemistry
  • Antirheumatic Agents / pharmacology
  • Arthritis, Experimental / drug therapy
  • Arthritis, Experimental / pathology
  • Cell Line
  • Creatine Kinase / metabolism
  • Crystallography, X-Ray
  • Estrogen Receptor alpha / genetics
  • Estrogen Receptor alpha / physiology*
  • Estrogen Receptor beta / genetics
  • Estrogen Receptor beta / physiology*
  • Humans
  • Inflammatory Bowel Diseases / drug therapy
  • Luciferases / genetics
  • Mice
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / biosynthesis
  • NF-kappa B / genetics
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Propionates / pharmacology
  • Rats
  • Rats, Inbred Lew
  • Rats, Sprague-Dawley
  • Stereoisomerism
  • Structure-Activity Relationship
  • Transcriptional Activation

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic Agents
  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • NF-kappa B
  • Nitriles
  • Propionates
  • Luciferases
  • Creatine Kinase