Nitroxyl (HNO) has gained attention based on its distinctive biological properties, having use as a cardiovascular therapeutic agent that works by improving post-ischemic contractility. HNO dimerizes rapidly and irreversibly, necessitating the use of HNO-generating systems for its use in drug therapy. Acyl nitroso compounds are known donors of HNO, but are also unstable. We synthesized several acyl nitroso compounds with 9,10-dimethylanthracene cycloadducts structural motifs. It was expected that these cycloadducts would provide a stable form of the acyl nitroso compound that undergoes a Retro Diels-Alder reaction and generate HNO.  The synthesized compounds were characterized using Nuclear Magnetic Resonance spectroscopy. Two acyl nitroso-9,10-dimethylanthracene cycloadducts have been synthesized and characterized. The yields of their reactions are 31% and 19% respectively. Preliminary research has shown that these compounds do generate HNO. The production of HNO via Retro Diels-Alder reaction will allow for HNO to exist as a chemically reactive agent in biological systems.

Production of nitroxyl from acyl nitroso compounds via retro Diels-Alder reaction

245th National Meeting (2013)

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