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Synthesis and Antitumor Activity of C-3(R) Hydroxy Modified Betulinic Acid Derivatives

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Chemistry of Natural Compounds Aims and scope

Four novel betulinic acid (BA) derivatives modified at the C-3 position were prepared by the Mitsunobu reaction and subsequently evaluated for antitumor activity against four common cancer cell lines in vitro. The results from the MTT assay revealed that the four tested compounds showed remarkable cytotoxic activity against four cancer cell lines, much better than BA. Western blotting results indicated that the four compounds, especially compound 2c, caused a significant up-regulation expression of the caspase-12 in CT26 cell. Our results showed that configuration inversions of chiral C-3 of BA could also produce BA derivatives with potent antitumor activity.

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Acknowledgment

This work was supported by the National Key R&D Program of China (2016YFD0600805), the Jiangsu “333” project of cultivation of high-level talents, the 11th Six Talents Peak Project of Jiangsu Province, a Project Funded by the National First-class Disciplines (PNFD), a project funded by the priority academic program development of Jiangsu Higher Education Institutions (PAPD), and the Doctorate Fellowship Foundation of Nanjing Forestry University (163030748).

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Authors and Affiliations

  1. Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University, 159 Long Pan Road, 210037, Nanjing, P. R. China

    Pan Yu, Pan Yu, Dong-dong Li, Chao-jie Xia & Lin-guo Zhao

  2. College of Chemical Engineering, Nanjing Forestry University, 159 Long Pan Road, 210037, Nanjing, P. R. China

    Pan Yu, Dong-dong Li, Jun-jun Ni, Chao-jie Xia & Lin-guo Zhao

  3. Jiangsu Kanion Pharmaceutical Co., Ltd., 58 Haichang South Road, Lianyungang, 222001, Jiangsu Province, P. R. China

    Zhen-zhong Wang, Wei Xiao & Gang Ding

Authors
  1. Pan Yu
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  2. Dong-dong Li
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  3. Jun-jun Ni
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  4. Chao-jie Xia
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  5. Zhen-zhong Wang
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  6. Wei Xiao
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  7. Gang Ding
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  8. Lin-guo Zhao
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Corresponding authors

Correspondence to Wei Xiao or Lin-guo Zhao.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2019, pp. 930–933.

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Yu, P., Li, Dd., Ni, Jj. et al. Synthesis and Antitumor Activity of C-3(R) Hydroxy Modified Betulinic Acid Derivatives. Chem Nat Compd 55, 1080–1084 (2019). https://doi.org/10.1007/s10600-019-02899-x

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  • DOI: https://doi.org/10.1007/s10600-019-02899-x

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