Reduction of nitroxides by anthralin and some of its derivatives.
In DMSO solution, anthralin and its C-10 monosubstituted derivatives reduce nitroxides to the corresponding hydroxylamine derivatives, which are not further transformed. The reaction rate depends on the solvent used, the nitroxide, and the structure of the reducer. It is faster in DMSO than in DMF, piperidine type of nitroxides are reduced faster than the pyrrolidine type, and the substitution on C-10 of anthralin has a significant influence on the reaction rate. Anthralin derivatives without protons at C-10 are not able to reduce nitroxides.
Pecar
S
S
Department of Pharmacy, Faculty of Natural Sciences and Technology, University of Ljubljana, Republic of Slovenia.
Schara
M
M
Müller
K
K
Wiegrebe
W
W
D000287:Administration, Topical; D000875:Anthralin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000378:metabolism; D004121:Dimethyl Sulfoxide; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D066298:In Vitro Techniques; D007700:Kinetics; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D012996:Solutions; D013329:Structure-Activity Relationship
D000893:Anti-Inflammatory Agents; D005609:Free Radicals; D009589:Nitrogen Oxides; D012996:Solutions; D000875:Anthralin; D004121:Dimethyl Sulfoxide