Facile Synthesis and NO-Generating Property of 4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-Oxides.
4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxides (2) are conveniently prepared in high yields by the oxidative intramolecular cyclization of 6-amino-5-nitro-1H-pyrimidine-2,4-diones (1) employing iodosylbenzene diacetate as an oxidant in the presence of lithium hydride. The generation of nitric oxide (NO) and NO-related species from 2 occurs in the presence of thiols such as N-acetylcysteamine, cysteine, and glutathione under physiological conditions. The evidence for the NO generation derives from mechanistic interpretations for the reaction of 2 with thiols and other chemical observations.
Sako
Magoichi
M
Gifu Pharmaceutical University, 5-6-1, Mitahora-higashi, Gifu 502-8585, Japan.
Oda
Souichi
S
Ohara
Seiji
S
Hirota
Kosaku
K
Maki
Yoshifumi
Y