Synthesis and study of 2-amino-7-bromofluorenes modified with nitroxides and their precursors as dual anti-amyloid and antioxidant active compounds

Eur J Med Chem. 2011 Apr;46(4):1348-55. doi: 10.1016/j.ejmech.2011.01.059. Epub 2011 Feb 3.

Abstract

A series of 2-aminofluorenes N-alkylated with nitroxides or their precursors were synthesized. The new compounds were tested on hydroxyl radical and peroxyl radical scavenging ability and inflammatory assay on the endothelial brain cells. In agreement with ROS scavenging ability the same compound 7-bromo-N -[(1-Oxyl-2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridine-4yl)methyl]-9H-fluoren-2-amine (3b) and its hydroxylamine salt (3b/OH/HCl) showed the anti-inflammatory property on the endothelial brain cells.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amyloid / chemistry*
  • Cell Line
  • Electron Spin Resonance Spectroscopy
  • Endothelial Cells / drug effects
  • Endothelial Cells / metabolism
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Fluorenes / pharmacology*
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • Humans
  • Hydroxyl Radical / chemistry
  • Lipolysis / drug effects
  • Nitrogen Oxides / chemistry*
  • Peroxides / chemistry
  • Protein Multimerization / drug effects*
  • Protein Structure, Secondary

Substances

  • Amyloid
  • Fluorenes
  • Free Radical Scavengers
  • Nitrogen Oxides
  • Peroxides
  • perhydroxyl radical
  • Hydroxyl Radical
  • nitroxyl