Release of nitrosating species in the course of reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides.
[reaction: see text] The reduction of benzo-1,2,3,4-tetrazine 1,3-dioxides (BTDOs) 1 with Na(2)S(2)O(4) or SnCl(2) is suggested to proceed via intermediate N-nitrosobenzotriazoles 3 to afford benzotriazoles 2. The (15)N-labeling experiments exhibit that the N-3 atom of the tetrazine ring is incorporated into the nitroso group of 3 that is ultimately released into solution. It is possible that the biological activity of BTDOs is due to their ability to release nitrosating species, i.e., N-nitrosotriazol 3 or HNO(2), in the course of reduction.
Ratnikov
Maxim O
MO
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation.
Lipilin
Dmitry L
DL
Churakov
Aleksandr M
AM
Strelenko
Yuri A
YA
Tartakovsky
Vladimir A
VA
D009569:Nitric Oxide / Q000378:metabolism; D010084:Oxidation-Reduction; D014230:Triazoles / Q000737:chemistry* / Q000378:metabolism*
D014230:Triazoles; D009569:Nitric Oxide