Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2236-2241.DOI: 10.6023/cjoc201602023 Previous Articles     Next Articles



李泽民a, 黄道锐a, 马丛明b, 许晓娟c, 刘祖亮b, 姚其正a   

  1. a 中国药科大学药学院 南京 210009;
    b 南京理工大学化工学院 南京 210094;
    c 盐城师范学院化学化工学院 盐城 224002
  • 收稿日期:2016-02-24 修回日期:2016-04-15 发布日期:2016-05-06
  • 通讯作者: 姚其正
  • 基金资助:


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

Li Zemina, Huang Daoruia, Ma Congmingb, Xu Xiaojuanc, Liu Zuliangb, Yao Qizhenga   

  1. 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
  • Received:2016-02-24 Revised:2016-04-15 Published:2016-05-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21102125).

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.

Key words: pyridofuroxans, aminative ring-opening reaction, 3-nitrosopyridine, tautomer, anticancer activity