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).
Similar content being viewed by others
References
S. M. Kupchan, M. A. Eakin, and A. M. Thomas, J. Med. Chem., 14, 1147 (1971).
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).
G. S. Xu, X. Y. Chen, and D. Q. Yu, Acta Pharm. Sin., 23, 122 (1988).
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).
A. C. Schmidt, Drugs, 64, 2031 (2004).
A. Moscona, N. Engl. J. Med., 353, 1363 (2005).
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).
J. Zhao and H. A. Aisa, Bioorg. Med. Chem. Lett., 22, 2321 (2012).
M. Obul, X. Wang, J. Zhao, G. Li, H. A. Aisa, and G. Huang, Mol. Diversity, 23, 1 (2019).
G. Li, J. Y. Zhao, C. Niu, L. F. Nie, C. Z. Dong, and H. A. Aisa, Bioorg. Med. Chem. Lett., 27, 1484 (2017).
J. P. Yong and H. A. Aisa, Chem. Nat. Compd., 44, 311 (2008).
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).
L. Chen, M. Obul, K. Bozorov, and J. Zhao, Chem. Nat. Compd., 57, 854 (2021).
Z. Ruzi, K. Bozorov, L. Nie, J. Zhao, and H. A. Aisa, Biomed. Pharmacother., 156, 113948 (2022).
Z. Ruzi, K. Bozorov, L. Nie, J. Zhao, and H. Akber Aisa, Bioorg. Chem., 135, 106506 (2023).
Z. Ruzi, L. Nie, K. Bozorov, J. Zhao, and H. A. Aisa, Arch. Pharm., 354, 2000470 (2021).
Y. Zeng, L. Nie, K. Bozorov, Z. Ruzi, B. Song, J. Zhao, and H. A. Aisa, J. Heterocycl. Chem., 59, 555 (2022).
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).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 930–935.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-023-04205-2