Chinese Journal of Organic Chemistry >
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).
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.
Gan Ying , He Lihua , Zhang Yahong , Wang Jianhong , Zhao Jin . Synthesis and Biological Activity of Anthraquinone-polyamine Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 589 -595 . DOI: 10.6023/cjoc201309010
[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.
/
| 〈 |
|
〉 |
