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Synthesis via the Mannich Reaction and Biological Activity of Novel Fluorinated Camptothecin Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Two series of fluorinated camptothecin derivatives had been designed and synthesized via the Mannich reaction. The hexacyclic fluorinated camptothecin derivatives were found to be more active. (9S,10S)-2-Cyclopropyl-9-ethyl-10-fluoro-9-hydroxy-2,3,9,10,12,15-hexahydro-1H,13H-[1,3]oxazino[5,6-f]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-13-one showed potent antitumor activity against A549 and T24 cell lines with effective topoisomerase I inhibitory activity.

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References

  1. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.

    Article  CAS  Google Scholar 

  2. Richardson, P. Expert Opin. Drug Discovery 2016, 11, 983.

    Article  CAS  Google Scholar 

  3. Yerien, D. E.; Bonesi, S.; Postigo, A. Org. Biomol. Chem. 2016, 14, 8398.

    Article  CAS  Google Scholar 

  4. Wang, B.-C.; Wang, L.-J.; Jiang, B.; Wang, S.-Y.; Wu, N.; Li, X.-Q.; Shi, D.-Y. Mini-Rev. Med. Chem. 2017, 17, 683.

    Article  CAS  Google Scholar 

  5. Mei, H.; Han, J.; Klika, K. D.; Izawa, K.; Sato, T.; Meanwell, N. A.; Soloshonok, V. A. Eur. J. Med. Chem. 2020, 186, 111826.

    Article  CAS  Google Scholar 

  6. Kuznecovs, J.; Baskevics, V.; Orlova, N.; Belyakov, S.; Domračeva, I.; Vorona, M.; Veinberg, G. Chem. Heterocycl. Compd. 2020, 56, 1297. [Khim. Geterotsikl. Soedin. 2020, 56, 1297.]

  7. Zhuang, C.; Wu, Y.; Zhang, W.; Miao, Z. In Natural Products in Clinical Trials; Atta-ur-Rahman; Anjum, S.; El-Seedi, H. R., Eds.; Bentham Science Publishers: Sharjah, 2020, Vol. 2, p. 123.

  8. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.

    Article  Google Scholar 

  9. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.

    Article  CAS  Google Scholar 

  10. Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.

    Article  CAS  Google Scholar 

  11. Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.

    Article  CAS  Google Scholar 

  12. Miao, Z.; Zhu, L.; Dong, G.; Zhuang, C.; Wu, Y.; Wang, S.; Guo, Z.; Liu, Y.; Wu, S.; Zhu, S.; Fang, K.; Yao, J.; Li, J.; Sheng, C.; Zhang, W. J. Med. Chem. 2013, 56, 7902.

    Article  CAS  Google Scholar 

  13. Wu, Y.; Zhu, L.; Sheng, C.; Yao, J.; Miao, Z.; Zhang, W.; Wei, Y.; Shi, R. J. Fluorine Chem. 2014, 157, 48.

    Article  CAS  Google Scholar 

  14. Ma, H.; Chen, B.; Wang, Y.; Wang, C.; Yao, J.; Zhang, W.; Miao, Z. Chem. Biodiversity 2020, 17, e2000068.

    Article  CAS  Google Scholar 

  15. Yang, C.-J.; Song, Z.-L.; Goto, M.; Hsu, P.-L.; Zhang, X.-S.; Yang, Q.-R.; Liu, Y.-Q.; Wang, M.-J.; Morris-Natschke, S. L.; Shang, X.-F.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2017, 27, 4694.

    Article  CAS  Google Scholar 

  16. Biersack, B.; Ahmed, K.; Padhye, S.; Schobert, R. Expert Opin. Drug Discovery 2018, 13, 39.

    Article  CAS  Google Scholar 

  17. Roman, G. Eur. J. Med. Chem. 2015, 89, 743.

    Article  CAS  Google Scholar 

  18. Lukashenko, A. V.; Osipov, D. V.; Osyanin, V. А.; Klimochkin, Yu. N. Chem. Heterocyclic Compd. 2020, 56, 529. [Khim. Geterotsikl. Soedin. 2020, 56, 529.]

  19. Xu, T.; Zheng, Z.; Guo, Y.; Bai, L.-P. Eur. J. Med. Chem. 2020, 205, 112663.

    Article  CAS  Google Scholar 

  20. Bracher, F.; Tremmel, T. Arch. Pharm. 2017, 350, e1600236.

    Article  Google Scholar 

  21. The PyMOL Molecular Graphics System, Version 2.5; Schrödinger, LLC. https://www.schrodinger.com/products/pymol

  22. AutoDock, Version 4.2.6; The Scripps Research Institute. http://autodock.scripps.edu/

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Authors and Affiliations

  1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, China

    Chuanhao Wang, Yazhao Zhu & Yuelin Wu

  2. School of Pharmacy, Ningxia Medical University, 1160 Shengli St, Yinchuan, 750004, Ningxia, China

    Yuan Wang & Haijun Ma

  3. School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai, 200433, China

    Yanming Zhang & Zhenyuan Miao

Authors
  1. Chuanhao Wang
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  2. Yuan Wang
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  3. Haijun Ma
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  4. Yazhao Zhu
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  5. Yanming Zhang
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  6. Zhenyuan Miao
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  7. Yuelin Wu
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Corresponding authors

Correspondence to Zhenyuan Miao or Yuelin Wu.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(6), 704–708

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Wang, C., Wang, Y., Ma, H. et al. Synthesis via the Mannich Reaction and Biological Activity of Novel Fluorinated Camptothecin Derivatives. Chem Heterocycl Comp 57, 704–708 (2021). https://doi.org/10.1007/s10593-021-02971-x

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  • DOI: https://doi.org/10.1007/s10593-021-02971-x

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