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Facile Synthesis and NO-Generating Property of 4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-Oxides.

The Journal of organic chemistry (2001-10-24)
Magoichi Sako, Souichi Oda, Seiji Ohara, Kosaku Hirota, Yoshifumi Maki
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N-Acetylcysteamine, 95%

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