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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 9: 2236 - 2241

DOI: https://doi.org/10.6023/cjoc201602023

NOTE

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 Zemin ,
  • Huang Daorui ,
  • Ma Congming ,
  • Xu Xiaojuan ,
  • Liu Zuliang ,
  • Yao Qizheng
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  • 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 date: 2016-02-24

  Revised date: 2016-04-15

  Online published: 2016-05-06

Supported by

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

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Abstract

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

Cite this article

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

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