Nitroxyl (HNO) release from new functionalized N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts

Bioorg Med Chem Lett. 2004 Nov 15;14(22):5565-8. doi: 10.1016/j.bmcl.2004.08.062.

Abstract

A thermal retro-Diels-Alder decomposition of N-hydroxyurea-derived acyl nitroso compounds and 9,10-dimethylanthracene cycloadducts followed by acyl nitroso compound hydrolysis produces nitrous oxide, evidence for the formation of nitroxyl, the one-electron reduced form of nitric oxide that has drawn considerable attention for its potential roles in biological systems. EPR and NMR spectroscopy provide further evidence for nitroxyl formation and kinetic information, respectively. Such compounds may prove to be useful alternative nitroxyl donors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anthracenes / chemistry*
  • Cyclization
  • Hydrolysis
  • Hydroxyurea / chemistry
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis*
  • Nitroso Compounds / chemical synthesis*
  • Nitroso Compounds / chemistry

Substances

  • Anthracenes
  • Nitrogen Oxides
  • Nitroso Compounds
  • 9,10-dimethylanthracene
  • nitroxyl
  • Hydroxyurea