Synthesis and Reduction Kinetics of Five Ibuprofen-Nitroxides for Ascorbic Acid and Methyl Radicals

Chem Pharm Bull (Tokyo). 2016;64(10):1509-1513. doi: 10.1248/cpb.c16-00347.

Abstract

The hybrid compounds 1-5 comprised of five nitroxides with ibuprofen were synthesized and their reduction rate for ascorbic acid (AsA) and methyl radicals were measured in comparison with 3-hydroxy-tetramethylpyrrolidine-1-oxyl (PROXYL) 6. The rate constants in reduction reaction with 200-fold excess of AsA were determined in following order: 1 (0.42±0.06), 3 (0.17±0.06), 2 (0.10±0.05), and 6 (0.09±0.02 M-1s-1). The remaining two sterically shielded nitroxides 4 and 5 scarcely reacted with AsA. In the reaction with the more reactive methyl radicals, produced by 200-fold excess of Fenton's reagent, the reduction rates of 2, 4, and 5 were in the following decreasing order: 2 (1.1±0.2), 4 (0.76±0.09), and 5 (0.31±0.03 M-1s-1).

MeSH terms

  • Ascorbic Acid / chemical synthesis*
  • Ascorbic Acid / chemistry
  • Free Radicals / chemical synthesis
  • Free Radicals / chemistry
  • Ibuprofen / chemistry*
  • Kinetics
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis
  • Nitrogen Oxides / chemistry*
  • Oxidation-Reduction

Substances

  • Free Radicals
  • Nitrogen Oxides
  • Ascorbic Acid
  • Ibuprofen