Citation: Zhang Pingzhu, Wei Xiao, Liu Huan, Wang Qiwei, Ma Chen, Rong Ruixue, Li Xiaoliu. Synthesis and Cytotoxicity of Azasugar Modified Anthraquinone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1921-1925. doi: 10.6023/cjoc201602012 shu

Synthesis and Cytotoxicity of Azasugar Modified Anthraquinone Derivatives

1.
Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Li Xiaoliu, lixl@hbu.cn
Received Date: 16 February 2016
Revised Date: 26 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China Nos. 21172051, 21372059

Figures(2)

In order to develop the anti-tumor agents with high efficiency and low toxicity, a series of novel azasugar modified anthraquinone derivatives have been designed and synthesized by the ammonolysis of N-alkylamino azasugar with rhine and microwave assisted Ullmann coupling reaction of N-alkylamino azasugar with 1-amino-4-bromoanthraquinone-2-sulfonic acid. Their cytotoxic activities against Hela, A549, MCF-7 and MGC-803 cells were preliminarily evaluated.
- anthraquinone,
- rhein,
- azasugar,
- Ullmann coupling,
- cytotoxicity
1. [1]
  Monneret, C. Eur. J. Med. Chem. 2001, 36, 483.
2. [2]
  Buzdar, A. U.; Marcus, C.; Smith, T. L.; Blumenschein, G. R. Cancer 1985, 55, 2761.
3. [3]
  Bolger, T. A.; Yao, T. P. J. Neurosci. 2005, 25, 9544.
4. [4]
  Duraipandiyan, V.; Baskar, A. A.; Ignacimuthu, S.; Muthukumar, C. Al-Harbi, N. A. Asian Pac. J. Trop. Dis. 2012, 517.
5. [5]
  Huang, Q.; Lu, G.; Shen, H. M.; Cbung, M. C. M.; Ong, C. N. Med. Res. Rev. 2007, 27, 609.
6. [6]
  Panigrahi, G. K.; Yadav, A.; Srivastava, A.; Tripathi, A.; Raisuddin, S.; Das, M. Chem. Res. Toxicol. 2015, 28, 1133.
7. [7]
  Lin, Y. J.; Zhen, Y. S. Anti-cancer Drugs 2009, 20, 65.
8. [8]
  Yang, X.; Sun, G.; Yang, C.; Wang, B. H. ChemMedChem 2011, 6, 2294.
9. [9]
  Yao, G. Y.; Ye, M. Y.; Huang, R. Z.; Li, Y. J.; Pan, Y. M.; Xu, Q.; Liao, Z. X.; Wang, H. S. Bioorg. Med. Chem. Lett. 2014, 24, 501.
10. [10]
  Zhang, Z. H.; Yamashita, H.; Toyama, T.; Sugiura, H.; Omoto, Y.; Ando, Y.; Mita, K.; Hamaguchi, M.; Hayashi, S. I.; Iwase, H. Clin. Cancer Res. 2004, 10, 6962;
11. [11]
  Aldana-Masangkay, G. I.; Sakamoto, K. M. J. Biomed. Biotechnol. 2010, 2011.
12. [12]
  Glänzel, M.; Bültmann, R.; Starke, K.; Frahm, A. W. Eur. J. Med. Chem.2003, 38, 303.
13. [13]
  Glänzel, M.; Bültmann, R.; Starke, K.; Frahm, A. W. Eur. J. Med. Chem. 2005, 40, 1262.
14. [14]
  Baqi, Y.; Atzler, K.; Köse, M.; Glänzel, M.; Müller, C. E. J. Med. Chem. 2009, 52, 3784.
15. [15]
  Baqi, Y.; Lee, S. Y.; Iqbal, J.; Ripphausen, P.; Lehr, A.; Scheiff, A. B.; Zimmermann, H.; Bajorath, J.; Müller, C. E. J. Med. Chem. 2010, 53, 2076.
16. [16]
  Sears, P.; Wong, C. H. Angew. Chem., Int. Ed. 1999, 38, 2300.
17. [17]
  Compain, P.; Martin, O. R. Iminosugars: from Synthesis to Therapeutic Applications, John Wiley and Sons, Ltd., Chichester, 2007, p. 87.
18. [18]
  Zhang, P. Z.; Yang, H. L.; Li, C. C.; Xia, Z. C.; Wang, X. M.; Wei, H.; Rong, R. X.; Cao, Z. R.; Wang, K. R.; Chen, H.; Li, X. L. Chin. Chem. Lett. 2014, 25, 1057.
19. [19]
  Baqi, Y.; Muller, C. E. Org. Lett. 2007, 9, 1271.
20. [20]
  Mosmann, T. J. Immunol. Methods 1983, 65, 55.
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沈阳化工大学材料科学与工程学院沈阳 110142