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Synthesis and Cytotoxic Activity of a New Derivative of Rupestonic Acid

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Chemistry of Natural Compounds Aims and scope

Twenty new amide derivatives of rupestonic acid were synthesized. Their cytotoxic activities against four human cancer cell lines (HeLa, HT-29, A549, and HepG2) were established. Compound 2p was active against A549 (IC50 = 10.31 μM) and HepG2 cell lines (IC50 = 5.44 μM). Derivative 2q showed better cytotoxic activity against HeLa (IC50 = 7.95 μM) and HT-29 cancer cells (IC50 = 2.49 μM).

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References

  1. S. M. Kupchan, M. A. Eakin, and A. M. Thomas, J. Med. Chem., 14, 1147 (1971).

    Article  CAS  PubMed  Google Scholar 

  2. S. M. Kupchan, T. J. Giacobbe, I. S. Krull, S. M. Thomas, M. A. Eakin, and D. C. Fessler, J. Org. Chem., 35, 3539 (1970).

    Article  CAS  Google Scholar 

  3. G. S. Xu, X. Y. Chen, and D. Q. Yu, Acta Pharm. Sin., 23, 122 (1988).

    CAS  Google Scholar 

  4. C. U. Kim, W. Lew, M. A. Williams, H. Wu, L. Zhang, X. Chen, P. A. Escarpe, D. B. Mendel, W. G. Laver, and R. C. Stevens, J. Med. Chem., 41, 2451 (1998).

    Article  CAS  PubMed  Google Scholar 

  5. A. C. Schmidt, Drugs, 64, 2031 (2004).

    Article  CAS  PubMed  Google Scholar 

  6. A. Moscona, N. Engl. J. Med., 353, 1363 (2005).

    CAS  Google Scholar 

  7. R. J. Russell, L. F. Haire, D. J. Stevens, P. J. Collins, Y. P. Lin, G. M. Blackburn, A. J. Hay, S. J. Gamblin, and J. J. Skehel, Nature, 443, 45 (2006).

    Article  CAS  PubMed  Google Scholar 

  8. J. Zhao and H. A. Aisa, Bioorg. Med. Chem. Lett., 22, 2321 (2012).

    Article  CAS  PubMed  Google Scholar 

  9. M. Obul, X. Wang, J. Zhao, G. Li, H. A. Aisa, and G. Huang, Mol. Diversity, 23, 1 (2019).

    Article  CAS  Google Scholar 

  10. G. Li, J. Y. Zhao, C. Niu, L. F. Nie, C. Z. Dong, and H. A. Aisa, Bioorg. Med. Chem. Lett., 27, 1484 (2017).

    Article  CAS  PubMed  Google Scholar 

  11. J. P. Yong and H. A. Aisa, Chem. Nat. Compd., 44, 311 (2008).

    Article  CAS  Google Scholar 

  12. Y. W. He, C. Z. Dong, J. Y. Zhao, L. L. Ma, Y. H. Li, and H. A. Aisa, Eur. J. Med. Chem., 76, 245 (2014).

    Article  CAS  PubMed  Google Scholar 

  13. L. Chen, M. Obul, K. Bozorov, and J. Zhao, Chem. Nat. Compd., 57, 854 (2021).

    Article  CAS  Google Scholar 

  14. Z. Ruzi, K. Bozorov, L. Nie, J. Zhao, and H. A. Aisa, Biomed. Pharmacother., 156, 113948 (2022).

    Article  CAS  PubMed  Google Scholar 

  15. Z. Ruzi, K. Bozorov, L. Nie, J. Zhao, and H. Akber Aisa, Bioorg. Chem., 135, 106506 (2023).

  16. Z. Ruzi, L. Nie, K. Bozorov, J. Zhao, and H. A. Aisa, Arch. Pharm., 354, 2000470 (2021).

    Article  CAS  Google Scholar 

  17. Y. Zeng, L. Nie, K. Bozorov, Z. Ruzi, B. Song, J. Zhao, and H. A. Aisa, J. Heterocycl. Chem., 59, 555 (2022).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The work was financially supported by the West Light Foundation, Chinese Academy of Sciences (Grant No. 2020-XBQNXZ-007) and the National Program of Key Research and Development of China (Grant No. 2020YFE0205600).

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Correspondence to J. Zhao.

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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 930–935.

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Aibibula, P., Aisa, H.A., Bozorov, K. et al. Synthesis and Cytotoxic Activity of a New Derivative of Rupestonic Acid. Chem Nat Compd 59, 1102–1108 (2023). https://doi.org/10.1007/s10600-023-04205-2

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  • DOI: https://doi.org/10.1007/s10600-023-04205-2

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