New vadimezan hydrazones were synthesized as E/Z isomers and characterized by IR, 1H NMR, MS, and HRMS techniques; the ratio of isomers was analyzed by NOESY spectra. All compounds were evaluated for their cytotoxic activities against endometrial Ishikawa, lung A549 and NCI-460, chorion Bewo, cervical HeLa and Siha, breast MCF-7, leukemia HL-60, liver BEL-7402, and stomach BGC-823 cancer cell lines in vitro by standard MTT assay. The preliminary pharmacological results indicated that compound 5c exhibited most promising cytotoxic activity against NCI-460 cell line with IC50 value of 7.01 ± 0.53 μM.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Y. Na, J. Pharm. Pharmacol., 61, 707 – 712 (2009).
N. Pouli, P. Marakos, Anti-Cancer Agents Med. Chem., 9, 77 – 98 (2009).
M. M. M. Pinto, M. E. Sousa, and M. S. J. Nascimento, Curr. Med. Chem., 12, 2517 – 2538 (2005).
W. J. Liu, D. S. Mei, and W. H. Duan, Chinese Chem. Lett., 24, 515 – 517 (2013).
A. Isakovic, T. Jankovic, L. Harhaji, et al., Bioorg. Med. Chem., 16, 5683 – 5694 (2008).
K. Matsumoto, Y. Akao, E. Kobayashi, et al., J. Nat. Prod., 66, 1124 – 1127 (2003).
K. Matsumoto, Y. Akao, H. Yi, et al., Bioorg. Med. Chem., 12, 5799 – 5806 (2004).
Y. Kwok, Q. Zeng, and L. H. Hurley, Proc. Natl. Acad. Sci. USA, 95, 13531 – 13536 (1998).
M. Hansen, S.-J. Lee, J. M. Cassady, et al., J. Am. Chem. Soc., 118, 5553 – 5561 (1996).
H. R. El-Seedi, M. A. El-Barbary, D. M. H. El-Ghorab, et al., Curr. Med. Chem., 17, 854 – 901 (2010).
S. Boutefnouchet, N. T. Minh, R. Putrus, et al., Eur. J. Med. Chem., 45, 581 – 587 (2010).
S. Boutefnouchet, N. Gaboriaud-Kolar, N. T. Minh, et al., J. Med. Chem., 51, 7287 – 7297 (2008).
M. Y. Kim, Y. Na, H. Vankayalapati, et al., J. Med. Chem., 46, 2958 – 2972 (2003).
B. C. Baguley, The Lancet Oncol., 4, 141 – 148 (2003).
G. M. Tozer, C. Kanthou, and B. C. Baguley, Nature Rev., 5, 423 – 435 (2005).
J. W. Lippert, Bioorg. Med. Chem., 15, 605 – 615 (2007).
B. D. Palmer, K. Henare, S. T. Woon, et al., J. Med. Chem., 50, 3757 – 3764 (2007).
S. Gobbi, F. Belluti, A. Bisi, et al., Bioorg. Med. Chem., 14, 4101 – 4109 (2006).
H. Marona, E. Pekala, L. Antkiewicz-Michaluk, et al., Bioorg. Med. Chem., 16, 7234 – 7244 (2008).
S. J. Zhang, Z. S. Ding, F. S. Jiang, et al., Med. Chem. Commun., 5, 512 – 520 (2014).
C. M. Buchanan, J. H. Shih, J. W. Astin, et al., Clin. Sci., 122, 449 – 457 (2012).
J. W. Paxton, P. Kestell, D. Chiang, et al., Clin. Exp. Pharmacol. Physiol., 32, 633 – 639 (2005).
R. Giri, J. R. Goodell, C. Xing, et al., Bioorg. Med. Chem., 18, 1456 – 1463 (2010).
K. Gaukroger, J. A. Hadfield, L. A. Hepworth, et al., J. Org. Chem., 66, 8135 – 8138 (2001).
A. Aliabadi, A. Mohammadi-Frarni, M. Azizi, et al., Pham. Chem. J., 10, 694 – 699 (2016).
N. Campbell, S. R. McCallum, and D. J. Mackenzie, J. Chem. Soc., 1922 – 1924 (1957).
Acknowledgments
The work was supported by the Research Fund from Zhejiang Chinese Medical University (2011ZY26).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhang, SJ., Xu, F., Ge, QF. et al. Synthesis, Structural Characterization and Cancer Cell Cytotoxic Activity of Vadimezan Hydrazones. Pharm Chem J 50, 377–381 (2016). https://doi.org/10.1007/s11094-016-1455-5
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-016-1455-5