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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 4: 788 - 796

DOI: https://doi.org/10.6023/cjoc201309031

Articles

Synthesis and Anticancer Activities of C-13 Etheral Gibberellin Derivatives

  • Chen Jingbo ,
  • Sun Zhuxian ,
  • Zhang Yanli ,
  • Chen Jingchao ,
  • Li Penghui ,
  • Zeng Xianghui ,
  • Yin Benlin ,
  • Xie Yan ,
  • Qing Chen ,
  • Zhang Hongbin
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  • a Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091;
    b Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650031

Received date: 2013-09-23

  Revised date: 2013-12-05

  Online published: 2013-12-13

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21062029, 20925205), the Natural Science Foundation of Yunan Province (Nos. 2009CD007, 2010GA014) and the National Basic Research Program of China (973 Program, No. 2009CB522300).

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Abstract

C-13 ethereal gibberellin derivatives bearing two α,β-unsaturated ketones in A and D rings have been designed and synthesized. In vitro studies demonstrated that a number of the C-13 ethereal gibberellin derivatives showed strong anticancer activities in thiazolylblue (MTT) assay towards four human cancer cell lines including HT29, A-549, HepG2 and MKN28. Compound 27 was found to be the most potent compound (IC50=0.21 μmol·L-1 against MKN28) and more active than the positive control (DDP).

Key words： gibberellin; ether; α,β-unsaturated ketone; anticancer

Cite this article

Chen Jingbo , Sun Zhuxian , Zhang Yanli , Chen Jingchao , Li Penghui , Zeng Xianghui , Yin Benlin , Xie Yan , Qing Chen , Zhang Hongbin . Synthesis and Anticancer Activities of C-13 Etheral Gibberellin Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(4) : 788 -796 . DOI: 10.6023/cjoc201309031

References

[1] (a) Mander, L. N. Chem. Rev. 1992, 92, 573. (b) Mander, L. N. Nat. Prod. Rep. 2003, 20, 49.
[2] (a) MacMillan, J. Nat. Prod. Rep. 1997, 14, 221. (b) Hanson, J. R. Nat. Prod. Rep. 2006, 23, 875. (c) Keyzers, R. A.; Peter, T. N.; Davies-Coleman, M. T. Nat. Prod. Rep. 2006, 23, 321. (d) Hanson, J. R. Nat. Prod. Rep. 2007, 24, 1332.
[3] Sun, H.-D.; Huang, S.-X.; Han, Q.-B. Nat. Prod. Rep. 2006, 23, 673.
[4] (a) Zhao, Y.; Niu, X.-M; Qian, L.-P.; Liu, Z.-Y.; Zhao, Q.-S.; Sun, H.-D. Eur. J. Med. Chem. 2007, 42, 494. (b) He, F.; Xiao, W.; Pu, J.; Wu, Y.; Zhang, H.; Li, X; Zhao, Y.; Yang, L.; Chen, G.; Sun, H. Phytochemistry 2009, 70, 1462. (c) Aquila, S.; Weng, Z.-Y.; Zeng, Y.-Q.; Sun, H.-D.; Luis Rios, J. J. Nat. Prod. 2009, 72, 1269. (d) Mao, Z.; Li, Y.; Chen, J.; Wang, Y.; Zhang, H. Bioorg. Med. Chem. Lett. 2010, 20, 4116.
[5] (a) Ikezoe, T.; Yang, Y.; Bandobashi, K.; Saito, T.; Takemoto, S.; Machida, H.; Togitani, K.; Koeffler, H. P.; Taguchi, H. Mol. Cancer Ther. 2005, 4, 578. (b) Wang, L.; Zhao, W.-L.; Yan, J.-S.; Liu, P.; Sun, H.-P.; Zhou, G.-B.; Weng, Z.-Y.; Wu, W.-L.; Weng, X.-Q.; Sun, X.-J.; Chen, J.; Sun, H.-D.; Chen, S.-J. Cell Death Differ. 2007, 14, 306. (c) Zhang, Y.-W.; Jiang, X.-X.; Chen, Q.-S.; Shi, W.-Y.; Wang, L.; Sun, H.-D.; Shen, Z.-X.; Chen, Z.; Chen, S.-J.; Zhao, W.-L. Exp. Hematol. 2010, 38, 191.
[6] Chen, J.; Sun, Z.; Zhang, Y.; Zeng, X.; Qing, C.; Liu, J.; Li, L.; Zhang, H. Bioorg. Med. Chem. Lett. 2009, 19, 5496.
[7] (a) MacMillan, J.; Wills, C. L. J. Chem. Soc., Perkin Trans. 1 1986, 309. (b) Lombardo, L.; Mander, L. N.; Turner, J. V. Aust. J. Chem. 1981, 34, 745.
[8] Bhaskar, K. V.; Mander, L. N. Tetrahedron Lett. 1996, 37, 719.
[9] Dolan, S. C.; MacMillan, J. J. Chem. Soc., Perkin Trans. 1 1985, 2741.
[10] Liu, J.-P.; Zhang, H.-B.; Huang, S.-X.; Pu, J.-X.; Xiao, W.-L.; Zhang, X.-P.; Xiao, W.-D.; Lei, C.; Sun, H.-D. J. Heterocycl. Chem. 2012, 49, 571. (a) Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589. (b) Zhou, J.-J.; Yue, X.-F.; Han, J.-X.; Yang, W.-Y. Chin. J. Pharm. 1993, 24, 455.
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