Citation: Luan Tian, Quan Zheshan, Fang Yingquan, Yang Hongjing. Design, Synthesis and Antiproliferative Activity of Chrysin Derivatives Bearing Triazole Moieties[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 440-446. doi: 10.6023/cjoc201907012 shu

Design, Synthesis and Antiproliferative Activity of Chrysin Derivatives Bearing Triazole Moieties

a.
Department of Pharmacy, Chongqing Three Gorges Medical College, Chongqing 404120
b.
College of Pharmacy, Yanbian University, Yanji, Jilin 133002
c.
College of Pharmacy, Shenyang Medical College, Shenyang 110034

Corresponding author: Yang Hongjing, 40278667@qq.com
Received Date: 5 July 2019
Revised Date: 23 July 2019
Available Online: 12 February 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21662036)the National Natural Science Foundation of China 21662036

Figures(2)

Two series of novel chrysin derivatives were synthesized, and their antiproliferative activity was evaluated against six human cancer cell lines (MGC-803, BEL-7402, HepG2, HeLa, A549, and SGC-7901) using methyl thiazolyl tetrazolium (MTT) assay. Preliminary bioassay results indicated that 7-((1-(3-fluorophenyl)-1H-1, 2, 3-triazol-4-yl)methoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (1c) and 7-((1-(2-chlorophenyl)-1H-1, 2, 3-triazol-4-yl)methoxy)-5-hydroxy-2-phenyl-4H-chro-men-4-one (1g) exhibited significantly improved antiproliferative activities against the MGC-803 cell line when compared with the parent compound chrysin and the positive control drug 5-fluorouracil. It demonstrates that compounds 1c and 1g are potential agents for cancer therapy.
- chrysin,
- synthesis,
- triazole,
- derivatives,
- antiproliferation
1. [1]
  Chen, Y. H.; Yang, Z. S.; Wen, C. C.; Chang, Y. S.; Wang, B. C.; Hsiao, C. A.; Shih, T. L. Food Chem. 2012, 134, 717. doi: 10.1016/j.foodchem.2012.02.166
2. [2]
  Critchfield, J. W.; Butera, S. T.; Folks, T. M. AIDS Res. Hum. Retroviruses 1996, 12, 39. doi: 10.1089/aid.1996.12.39
3. [3]
  Du, Q.; Gu, X.; Cai, J.; Huang, M.; Su, M. Mol. Med. Rep. 2012, 6, 100.
4. [4]
  Gresa-Arribas, N.; Serratosa, J.; Saura, J.; Solã, C. J. Neurochem. 2010, 115, 526. doi: 10.1111/j.1471-4159.2010.06952.x
5. [5]
  Brown, E.; Hurd, N. S.; McCall, S.; Ceremuga, T. E. AANA J. 2007, 75, 333.
6. [6]
  Khoo, B. Y.; Chua, S. L.; Balaram, P. Int. J. Mol. Sci. 2010, 11, 2188. doi: 10.3390/ijms11052188
7. [7]
  Prabhakar, M. M.; Manoharan, S.; Baskaran, N.; Srinivasan, R.; Karthikeyan, S.; Wani, S. A. Int. J. Phram. Sci. 2012, 3, 89.
8. [8]
  Srinivasan, R.; Manoharan, S. J. Cell Tissue Res. 2011, 11, 2909.
9. [9]
  Yu, X. M.; Phan, T.; Patel, P. N.; Jaskula-Sztul, R.; Chen, H. Cancer 2013, 119, 774. doi: 10.1002/cncr.27742
10. [10]
  Tsuji, P. A.; Winn, R. N.; Walle, T. Chem. Biol. Interact. 2006, 164, 85. doi: 10.1016/j.cbi.2006.08.023
11. [11]
  Walle, U. K.; Galijatovic, A.; Walle, T. Biochem. Pharmacol. 1999, 58, 431. doi: 10.1016/S0006-2952(99)00133-1
12. [12]
  Dos Anjos, J. V.; Sinou, D.; De Melo, S. J.; Srivastava, R. M. Carbohydr. Res. 2007, 342, 2440. doi: 10.1016/j.carres.2007.07.011
13. [13]
  Luan, T.; Cao, L. H.; Deng, H.; Shen, Q. K.; Tian, Y. S.; Quan, Z. S. Molecules 2019, 24, 121.
14. [14]
  Liu, C. F.; Shen, Q. K.; Li, J. J.; Tian, Y. S.; Quan, Z. S. J. Enzym. Inhib. Med. Chem. 2017, 32, 1111. doi: 10.1080/14756366.2017.1344982
15. [15]
  Hu, K.; Wang, W.; Cheng, H.; Pan, S. S.; Ren, J. Med. Chem. Res. 2011, 20, 838. doi: 10.1007/s00044-010-9395-1
16. [16]
  Liu, J. W.; Taylor, S. F.; Dupart, P. S.; Arnold, C. L.; Sridhar, J.; Jiang, Q.; Wang, Y.; Skripnikova, E. V.; Zhao, M.; Foroozesh, M. J. Med. Chem. 2013, 56, 4082. doi: 10.1021/jm4003654
17. [17]
  Maingot, L.; Elbakali, J.; Dumont, J.; Bosc, D.; Cousaert, N.; Urban, A.; Deglane G.; Villoutreix, B.; Nagase, H.; Sperandio, O.; Leroux, F.; Deprez, B.; Deprez-Poulain, R. Eur. J. Med. Chem. 2013, 69, 244. doi: 10.1016/j.ejmech.2013.08.027
18. [18]
  Zou, X. Q.; Peng, S. M.; Hu, C. P.; Tan, L. F.; Yuan, Q.; Deng, H. W.; Li, Y. J. Bioorg. Med. Chem. 2010, 18, 3020. doi: 10.1016/j.bmc.2010.03.056
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1.
沈阳化工大学材料科学与工程学院沈阳 110142