Convenient Aminative Ring-opening Reaction of 7-Amino-6-nitro-[1,2,5]oxadiazolo[3,4-b]pyridine-1-oxide and Antitumor Activity of Corresponding Products
2016
Reaction of 7-amino-6-nitro-[1,2,5]oxadiazolo[3,4-b]pyridine 1-oxide (1, namely pyridofuroxan) with ammonia or/and amines under mild conditions led to furoxan ring-opening, release of HNO and the formation of corresponding 5-nitro-3-nitroso-2,4-diaminopyridine 5a~5f. It is shown that the ring-opening reactivity of pyridofuroxan 1 was significantly affected by the 6-nitro substituent. The structures of all target compounds were identified by 1 H NMR, 13 C NMR and HRMS. The biological evaluation was performed on H522 (human lung cancer cell line) and U87 (glioma cell line) by 3-(4,5-dimethylthigal-2-yl)-2,5-(diphenyltetragalium) bromide (MTT) assay. The results suggested that all of the target compounds exhibited potent anti-tumor activities in vitro.
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