Organic Chemistry of Nitric Oxide for the Understanding of Its Physiological Roles

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Despite its simple structure, nitric oxide (NO) has been found to play diverse roles in biological systems. Accompanied by the positive physiological roles, NO causes extensive damage to the body in the case that NO is released at relatively higher concentration. In these circumstances, NO is activated by the reaction with various active oxygens to afford more reactive nitrogen oxides, and the ultimate reactive species included in the processes has been an important target for toxicological studies.For the understanding of reactive species of nitrogen oxides toward organic molecules, we have recently been studying the reaction of nitric oxide with nitrogen compounds in the presence and absence of oxygen, and found that oxygen plays two type of roles in this system, that is, one in which oxygen is consumed according to a stoichiometry, and the other where oxygen functions in a catalytic manner. With these results in hand, we next applied the reaction system to development of a new methodology of nitric oxide quenching, and found that N-aminoazaaromatics reacted rapidly with NO in the presence of various amounts of oxygen to afford corresponding deaminated products in quantitative yields. NO or higher nitrogen oxides was transformed stoichiometrically to nitrous oxide NィイD22ィエD2O. In addition, N-aminoazole derivatives were also found to quench superoxide anion, which is a precursor of peroxynitrite and other active oxygen species.