蒽醌-多胺缀合物的合成及生理活性研究
收稿日期: 2013-09-16
修回日期: 2013-10-24
网络出版日期: 2013-11-20
基金资助
国家自然科学基金（No. 21272056）；河南省科技厅（Nos. 112300413224，132300410228）资助项目.
Synthesis and Biological Activity of Anthraquinone-polyamine Derivatives
Received date: 2013-09-16
Revised date: 2013-10-24
Online published: 2013-11-20
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272056) and the Key Scientific and Technological Projects of Henan Province (Nos. 112300413224, 132300410228).
甘莹 , 何利华 , 张亚宏 , 王建红 , 赵瑾 . 蒽醌-多胺缀合物的合成及生理活性研究[J]. 有机化学, 2014 , 34(3) : 589 -595 . DOI: 10.6023/cjoc201309010
Seven anthraquinone-polyamine derivatives were designed and synthesized. The structures of the synthesized compounds were confirmed by 1H NMR, APCI-MS and elemental analysis. Prelimilary antitumor activity was invesitgated on K562, HepG2, MB231, Hela and HCT-116 cell lines by MTT (thiazolyl blue) assay. The results indicated that the target compounds obviously exhibited antitumor activity against the tested cell lines. Compounds 11b and 14c can intercalate to DNA with intensively fluorescence quenching in herring sperm DNA-EB system.
[1] Liang, Z. J.; Ai, J.; Ding, X.; Peng, X.; Zhang, D. Y.; Zhang, R. H.; Wang, Y.; Liu, F.; Zheng, M. Y.; Jiang, H. L.; Liu, H.; Geng, M. Y.; Luo, C. Med. Chem. Lett., 2013, 4, 408.
[2] Carroll, A. R.; Nash, B. D.; Duffy, S.; Avery, V. M. J. Nat. Prod. 2012, 75, 1206.
[3] Yang, K. L.; Wei, M. Y.; Shao, C. L.; Fu, X. M.; Guo, Z. Y.; Xu, R. F.; Zheng, C. J.; She, Z. G.; Lin, Y. C.; Wang, C. Y. J. Nat. Prod. 2012, 75, 935.
[4] Yan, Y. Y.; Zheng, L. S.; Zhang, X.; Chen, L. K.; Singh, S.; Wang, F.; Zhang, J. Y.; Liang, Y. J.; Dai, C. L.; Gu, L. Q.; Zeng, M. S.; Talele, T. T.; Chen, Z. S.; Fu, L. W. Mol. Pharm. 2011, 8, 1687.
[5] Igarashi, Y.; Trujillo, M. E.; Martínez-Molina, E.; Yanase, S.; Miyanaga, S.; Obata, T.; Sakurai, H.; Saiki, I.; Fujita, T.; Furumai, T. Bioorg. Med. Chem. Lett. 2007, 17, 3702.
[6] Cherng, J. M.; Chiang, W.; Wang, J. H.; Lin, C. M.; Lee, C. Y.; Shih, C. M.; Chiang, L. C. Food. Chem. 2008, 107, 1576.
[7] Rachel, E.; Airley, M.; Jane, E. Pharm. J. 2000, 264, 666.
[8] Karapcho, A. P.; Maresch, M. J.; Hacker, M. P.; Hazelhurst, L.; Menta, E.; Oliva, A.; Spinelli, S.; Beggiolin, G.; Giuliani, F. C.; Pezzoni, G.; Tognella, S. Curr. Med. Chem. 1995, 2, 803.
[9] de Isabella, P.; Palumbo, M.; Sissi, C.; Carenini, N.; Capranico, G.; Menta, E.; Oliva, A.; Spinelli, S.; Krapcho, A. P.; Giuliani, F. C.; Zunino, F. Biochem. Pharmacol. 1997, 53, 161.
[10] Krapcho, A. P.; Menta, E.; Oliva, A.; Domenico, R. D.; Fiocchi, L.; Maresch, M. E.; Gallagher, C. E.; Hacker, M. P.; Beggiolin, G.; Giuliani, F. C.; Pezzoni, G.; Spinelli, S. J. Med. Chem. 1998, 41, 5429.
[11] Sissi, C.; Moro, S.; Richter, S.; Gatto, B.; Menta, E.; Spinelli, S.; Krapcho, A. P.; Zunino, F.; Palumbo, M. Mol. Pharmacol. 2000, 59, 96.
[12] Hsin, L. W.; Wang, H. P.; Kao, P. H.; Lee, O.; Chen, W. R.; Chen, H. W.; Guh, J. H.; Chan, Y. L.; His, C. P.; Yang, M. S.; Li, T. K.; Lee, C. H. Bioorg. Med. Chem. 2008, 16, 1006.
[13] Adnan, N.; Buck, D. P.; Evison, B. J.; Cutts, S. M.; Phillips, D. R.; Collins, J. G. Org. Biomol. Chem. 2010, 8, 5359.
[14] Raschi, E.; Vasina, V.; Ursino, M. G.; Boriani, G.; Martoni, A.; De Ponti, F. Pharmacol. Ther. 2010, 125, 196.
[15] Cavalletti, E.; Crippa, L.; Mainardi, P.; Oggioni, N.; Cavagnoli, R.; Bellini, O.; Sala, F. Invest. New. Drugs 2007, 25, 187.
[16] Ruiz, J.; Vicente, C.; de Haro, C.; Espinosa, A. Inorg. Chem. 2011, 50, 2151.
[17] Gore, P. H.; Rahim, A.; Waters, D. N. J. Chem. Soc. B 1971, 202.
[18] Tam, M. N.; Nam, N. H.; Jin, G. Z.; Song, G. Y.; Ahn, B. Z. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 189.
[19] Cardia, M. C.; Begala, M.; DeLogu, A.; Maccioni, E. Farmaco 2001, 56, 549.
[20] Kuang, Y.-Q.; Zhang, S.-Y.; Wei, L.-L. Chem. Reag. 2001, 23, 359 (in Chinese).
(匡永清, 张生勇, 蔚琳琳, 化学试剂, 2001, 23, 359.)
[21] Jasys, V. J.; Kelbaugh, P. R.; Nason, D. M.; Phillips, D.; Rosnack, K. J.; Saccomano, N. A.; Stroh, J. G.; Volkmann, R. A.; Forman, J. T. J. Org. Chem. 1992, 57, 1814.
[22] Chong, H. S.; Torti, S. V.; Ma, R.; Torti, F. M.; Brechbiel, M. W. J. Med. Chem. 2004, 47, 5230.
[23] Hay, M. P.; Wilson, W. R.; Moselen, J. W.; Palmer, B. D.; Denny, W. A. J. Med. Chem. 1994, 37, 381.
[24] Tan, J. H.; Zhang, Q. X.; Huang, Z. S.; Chen, Y.; Wang, X. D.; Gu, L. Q.; Wu, J. Y. Eur. J. Med. Chem. 2006, 41, 1041.
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