Design, Synthesis and Antiproliferative Activities of Diaryl Thiourea Derivatives as Anticancer Agents
Jianwen Yao
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Search for more papers by this authorZuopeng He
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorJing Chen
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorDaquan Chen
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorWei Sun
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Search for more papers by this authorCorresponding Author
Wenfang Xu
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China, Tel.: 0086-531-88382264; Fax: 0086-531-88382264Search for more papers by this authorJianwen Yao
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Search for more papers by this authorZuopeng He
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorJing Chen
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorDaquan Chen
Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai, Shandong 264005, China
Search for more papers by this authorWei Sun
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Search for more papers by this authorCorresponding Author
Wenfang Xu
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China, Tel.: 0086-531-88382264; Fax: 0086-531-88382264Search for more papers by this authorAbstract
Two new series of diaryl thiourea containing sorafenib derivatives 9a–9t were designed and synthesized, and their antiproliferative activities against PC-3, HCT116 and MDA-MB-231 cell lines were evaluated. All compounds generally showed antiproliferative activity to PC-3 cells, most of the analogs exhibited potent antiproliferative activity to HCT116 cells, and compounds 9e, 9f, 9o and 9p demonstrated inhibitory activities against all three cell lines. The structures of all the newly synthesized compounds were determined by 1H NMR, 13C NMR and HRMS.
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REFERENCES
- 1 Liu, W.; Wang, S.; Yin, X.. Prog. Pharm. Sci., 2011, 35, 49 (in Chinese).
- 2 Petrelli, A.; Giordano, S.. Curr. Med. Chem., 2008, 15, 422.
- 3 Hanahan, D.; Weinberg, R. A.. Cell, 2000, 100, 57.
- 4 Adnane, L.; Trail, P. A.; Taylor, I.; Wilhelm, S. M.. Methods Enzymol., 2006, 407, 597.
- 5 Liu, L.; Cao, Y.; Chen, C.; Zhang, X.; McNabola, A.; Wilkie, D.; Wilhelm, S.; Lynch, M.; Carter, C.. Cancer Res., 2006, 66, 11851.
- 6 Wilhelm, S.; Carter, C.; Lynch, M.; Lowinger, T.; Dumas, J.; Smith, R. A.; Schwartz, B.; Simantov, R.; Kelley, S.. Nat. Rev. Drug Discov., 2006, 5, 835.
- 7 Guida, T.; Anaganti, S.; Provitera, L.; Gedrich, R.; Sullivan, E.; Wilhelm, S. M.; Santoro, M.; Carlomagno, F.. Clin. Cancer Res., 2007, 13, 3363.
- 8 Wilhelm, S. M.; Adnane, L.; Newell, P.; Villanueva, A.; Llovet, J. M.; Lynch, M.. Mol. Cancer Ther., 2008, 7, 3129.
- 9 Li, W.; Zhai, X.; Zhong, Z.; Li, G.; Pu, Y.; Gong, P.. Arch. Pharm., 2011, 344, 349.
- 10 Sun, M.; Wu, X.; Chen, J.; Cai, J.; Cao, M.; Ji, M.. Eur. J. Med. Chem., 2010, 45, 2299.
- 11 Dai, Y.; Hartandi, K.; Ji, Z.; Ahmed, A. A.; Albert, D. H.; Bauch, J. L.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Glaser, K. B.; Harris, C. M.; Hickman, D.; Guo, J.; Li, J.; Marcotte, P. A.; Marsh, K. C.; Moskey, M. D.; Martin, R. L.; Olson, A. M.; Osterling, D. J.; Pease, L. J.; Soni, N. B.; Stewart, K. D.; Stoll, V. S.; Tapang, P.; Reuter, D. R.; Davidsen, S. K.; Michaelides, M. R.. J. Med. Chem., 2007, 50, 1584.
- 12 Ménard, D.; Niculescu-Duvaz, I.; Dijkstra, H. P.; Niculescu-Duvaz, D.; Suijkerbuijk, B. M.; Zambon, A.; Nourry, A.; Roman, E.; Davies, L.; Manne, H. A.; Friedlos, F.; Kirk, R.; Whittaker, S.; Gill, A.; Taylor, R. D.; Marais, R.; Springer, C. J.. J. Med. Chem., 2009, 52, 3881.
- 13 Ramurthy, S.; Subramanian, S.; Aikawa, M.; Amiri, P.; Costales, A.; Dove, J.; Fong, S.; Jansen, J. M.; Levine, B.; Ma, S.; McBride, C. M.; Michaelian, J.; Pick, T.; Poon, D. J.; Girish, S.; Shafer, C. M.; Stuart, D.; Sung, L.; Renhowe, P. A.. J. Med. Chem., 2008, 51, 7049.
- 14 Potashman, M. H.; Bready, J.; Coxon, A.; DeMelfi, T. M., Jr.; DiPietro, L.; Doerr, N.; Elbaum, D.; Estrada, J.; Gallant, P.; Germain, J.; Gu, Y.; Harmange, J.-C.; Kaufman, S. A.; Kendall, R.; Kim, J. L.; Kumar, G. N.; Long, A. M.; Neervannan, S.; Patel, V. F.; Polverino, A.; Rose, P.; Van der Plas, S.; Whittington, D.; Zanon, R.; Zhao, H.. J. Med. Chem., 2007, 50, 4351.
- 15 Yang, Z.; Fang, Z.; Wang, Z.; Wei, P.. Acta Pharm. Sin., 2011, 46, 1093 (in Chinese).
- 16 Peng, W.; Zhang, X.; Zhang, C.; Wang, F.; You, Q.. Chin. J. New Drug, 2012, 21, 890 (in Chinese).
- 17 Zhang, J. M.; Yang, P. L.; Gray, N. S.. Nat. Rev. Cancer, 2009, 9, 28.
- 18 Yao, J.; Chen, J.; He, Z.; Sun, W.; Xu, W.. Bioorg. Med. Chem., 2012, 20, 2923.
