Synthesis and structure-activity relationship of cyclopentenone oximes as novel inhibitors of the production of tumor necrosis factor-α

Bioorg Med Chem Lett. 2014 Jul 1;24(13):2807-10. doi: 10.1016/j.bmcl.2014.04.115. Epub 2014 May 9.

Abstract

3-Alkyl-2-aryl-2-cyclopenten-1-one oxime derivatives (1) were studied as a novel class of inhibitors of tumor necrosis factor α (TNF-α) with regard to synthesis and in vitro SAR inhibition of TNF-α. The in vitro IC50 values of these compounds in rat and human peripheral blood mononuclear cells were at the sub-micromolar level.

Keywords: Cyclopentenone oximes; PBMCs; SAR; TNF-α.

MeSH terms

  • Animals
  • Cyclopentanes / chemistry*
  • Cyclopentanes / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Leukocytes, Mononuclear / chemistry
  • Leukocytes, Mononuclear / metabolism
  • Models, Molecular
  • Molecular Structure
  • Oximes / chemistry*
  • Oximes / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Cyclopentanes
  • Oximes
  • Tumor Necrosis Factor-alpha
  • cyclopentenone