Citation: Meng Yanqiu, Cao Jia, Tang Yi, Lu Xueyu, Liu Liwei. Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1080-1087. doi: 10.6023/cjoc201510034 shu

Synthesis and Anti-tumor Activity of Derivatives of Ring A of Ursolic Acid

1.
Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Corresponding author: Meng Yanqiu, mengyanqiu@hotmail.com
Received Date: 28 October 2015
Revised Date: 16 December 2015

Fund Project: and the Science and Technology Project in Shenyang No.F16-230-6-00Project supported by the National Natural Science Foundation of China No.21372156the Education Department of Higher School Outstanding Talent Support Program in Liaoning Province No.LR2013017

Figures(4)

Ten derivatives were successfully synthesized by the introduction of nitrogen-and oxygen-containing heterocyclic compounds at ring A and the modification of the amidation at C(28) position in the natural product ursolic acid, which structures were characterized by ¹H NMR, ¹³C NMR, MS and elemental analysis. Their anti-tumor activities against KB and SGC7901 cells in vitro were evaluated by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. These results indicated that all of derivatives can inhibit cell proliferation of KB and SGC7901 cells better than ursolic acid (UA), and UA_4-1 (IC₅₀=0. 289 μmol/L) and UA_4-2 (IC₅₀=0. 04 μmol/L) were also found to have especially more potent inhibitory activity on SGC7901 tumor cells than that of the positive control drug gefitinib (IC₅₀=1. 03 μmol/L).
- pentacyclic trierpenoid,
- ursolic acid,
- anti-tumor activity
1. [1]
2. [2]
  Kazakova, O. B.; Giniyatullina, G. V.; Yamansarov, E. Y.; Tolstikov, G. A. Bioorg. Med. Chem. Lett. 2010, 20, 4088.
3. [3]
  Cunha, W. R.; de Matos, G. X.; Souza, M. G.; Tozatti, M. G.; Andrade, E.; Silva, M. L.; Martins, C. H.; da Silva, R.; Da Silva Filho, A. A. Pharm. Biol.2010, 48, 166.
4. [4]
  Jin, Y. R.; Jin, J. L.; Li, C. H.; Piao, X. X.; Jin, N. G. Pharm. Biol. 2012, 50, 523.
5. [5]
  Liu, W.; Tan, X.; Shu, L.; Sun, H.; Song, J.; Jin, P.; Yu, S.; Sun, M.; Jia, X. Molecules 2012, 17, 9104.
6. [6]
  Wang, J.; Liu, L.; Qiu, H.; Zhang, X.; Guo, W.; Chen, W.; Tian, Y.; Fu, L.; Shi, D.; Cheng, J.; Huang, W.; Deng, W. PLoS One 2013, 8, 63872.
7. [7]
  Leal, A. S.; Wang, R.; Salvador, J. A.; Jing, Y. Bioorg. Med. Chem. 2012, 20, 5774.
8. [8]
  Nobuchika, S.; Kouhei, T.; Nicole, H.; Kenji, D.; Reiko, T.; Shiro, M. J. Biol. Chem. 2009, 284, 5000.
9. [9]
  Meng, Y. Q.; Zhan, L. F. J. Asian Nat. Prod. Res. 2015, 11, 1.
10. [10]
  Fu, H. J.; Zhou, Y. R.; Bao, B. H.; Jia, M. X.; Zhao, Y.; Zhang, L.; Li, J. X.; He, H. L.; Zhou, X. M. J. Med. Chem. 2014, 57, 4692.
11. [11]
  Liu, D.; Meng, Y. Q.; Zhao, J. Chem. Res. Chin. Univ. 2008, 24, 42.
12. [12]
13. [13]
14. [14]
15. [15]
  Meng, Y. Q. Bioorg. Med. Chem. 2009, 17, 848.
16. [16]
  Chen, J.; Fu, H.; Wang, Z.; Yin, F.; Li, J.; Hua, Y. Cell. Phys. Biochem. 2014, 34, 724.
17. [17]
  Fu, H. J.; Yang, Z.; Zhou, Y. R.; Bao, B. H.; Yun, D.; Li, J. X. Eur. J. Pharm. Sci. 2015, 76, 33.
18. [18]
  Chen, J.; Liu, J.; Zhang, L. Y.; Wu, G. Z.; Hua, W. Y.; Wu, X. M.; Sun, H. B. Bioorg. Med. Chem. Lett. 2006, 16, 2915.
19. [19]
  Qiu, W. W.; Shen, Q.; Yang, F.; Wang, B.; Zou, H.; Li, J. Y.; Li, J.; Tang, J. Bioorg. Med. Chem. Lett. 2009, 19, 6618.
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沈阳化工大学材料科学与工程学院沈阳 110142