Synthesis and characterization of several carbamoyl- and methylcarbamoyl-substituted EMPO derivatives

Bioorg Med Chem. 2009 Nov 1;17(21):7572-84. doi: 10.1016/j.bmc.2009.09.006. Epub 2009 Sep 6.

Abstract

The spin trapping behavior of four novel carbamoyl-substituted EMPO derivatives, namely 5-carbamoyl-3,5-dimethyl-pyrroline N-oxide (CADMPO), 3,5-dimethyl-5-methylcarbamoyl-pyrroline N-oxide (DMMCAPO), 5-carbamoyl-3-ethyl-5-methyl-pyrroline N-oxide (CAEMPO), and 3-ethyl-5-methyl-5-methylcarbamoyl-pyrroline N-oxide (EMMCAPO), towards different oxygen- and carbon-centered radicals is described, the half lives of the respective superoxide adducts ranging from about 10 to 20 min. The most characteristic adducts were, however, formed from methyl, hydroxymethyl, hydroxyethyl, and carbon dioxide anion radicals.

MeSH terms

  • Cyclic N-Oxides / chemical synthesis*
  • Cyclic N-Oxides / chemistry
  • Cyclic N-Oxides / pharmacology
  • Free Radicals / chemistry
  • Free Radicals / metabolism
  • Magnetic Resonance Spectroscopy
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Pyrroles / pharmacology
  • Spectrophotometry, Infrared
  • Spin Trapping
  • Superoxides / chemistry
  • Superoxides / metabolism

Substances

  • 2-ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide
  • Cyclic N-Oxides
  • Free Radicals
  • Pyrroles
  • Superoxides