Highly potent inhibitors of TNF-alpha production. Part II: metabolic stabilization of a newly found chemical lead and conformational analysis of an active diastereoisomer

Bioorg Med Chem. 2002 Dec;10(12):3787-805. doi: 10.1016/s0968-0896(02)00380-2.

Abstract

Design and synthesis of metabolically stabilized inhibitors of TNF-alpha production, which could be new drug candidates, are reported. Conformational analysis of an active diastereoisomer was performed based on biological evaluations of the conformationally fixed indane derivatives 17 and 18. Structure-activity relationships (SARs) based on biological evaluations of the optically active derivatives are also discussed. Full details including chemistry are reported.

MeSH terms

  • Animals
  • Chemical and Drug Induced Liver Injury / drug therapy
  • Drug Stability
  • Indans / chemical synthesis*
  • Indans / chemistry
  • Indans / pharmacology*
  • Injections, Intravenous
  • Lipopolysaccharides / pharmacology
  • Maximum Tolerated Dose
  • Mice
  • Molecular Conformation
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / pharmacology
  • Rats
  • Shock, Septic / chemically induced
  • Shock, Septic / drug therapy
  • Stereoisomerism
  • Structure-Activity Relationship
  • Survival Rate
  • Tissue Distribution
  • Tumor Necrosis Factor-alpha / analysis
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Indans
  • Lipopolysaccharides
  • Organophosphorus Compounds
  • Tumor Necrosis Factor-alpha