Citation: Li Zemin, Huang Daorui, Ma Congming, Xu Xiaojuan, Liu Zuliang, Yao Qizheng. 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[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2236-2241. doi: 10.6023/cjoc201602023 shu

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

a.
School of Pharmacy, China Pharmaceutical University, Nanjing 210009
b.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094
c.
Department of Chemistry, Yancheng Teachers University, Yancheng 224002

Corresponding author: Yao Qizheng, qz_yao@163.com
Received Date: 24 February 2016
Revised Date: 15 April 2016

Fund Project: National Natural Science Foundation of China 21102125

Figures(4)

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 let to the 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 ¹H NMR, ¹³C NMR and HRMS. The biological evaluation was performed on human lung cancer cell line (H522) and glioma cell line (U87) 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.
- pyridofuroxans,
- aminative ring-opening reaction,
- 3-nitrosopyridine,
- tautomer,
- anticancer activity
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