jo980732y_si_001.pdf (434.36 kB)
Download fileFacile Synthesis and NO-Generating Property of 4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-Oxides
journal contribution
posted on 05.09.1998, 00:00 authored by Magoichi Sako, Souichi Oda, Seiji Ohara, Kosaku Hirota, Yoshifumi Maki4H-[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.