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

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.

Graphical abstract2-Aminofluorenes N-alkylated with nitroxides were synthesized and three compounds have beneficial effects on inflammatory processes of endothelial brain cells.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► A new series of 7-bromo-2-aminofluorene compounds modified with nitroxides and their precursors were synthesized as dual (anti-amyloid and antioxidant) active compounds. ► Fluorene modified with six-membered nitroxide produced both ROS scavenge property and antiinflammatory property on the endothelial brain cells. ► The additions of the anti-oxidant and anti-inflammatory activities to fluorenes provide a novel approach for treating AD.