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Synthesis and Cytotoxicity Evaluation of Tropinone Derivatives |
| Xiu-Juan Yin1,2, Chang-An Geng1,3, Xing-Long Chen1,2, Chang-Li Sun1, Tong-Hua Yang1,3, Tian-Ze Li1,3, Jun Zhou1, Xue-Mei Zhang1,3, Ji-Jun Chen1,3 |
1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. University of Chinese Academy of Sciences, Beijing 100049, China;
3. Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China |
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Abstract Sixteen tropinone derivatives were prepared,and their antitumor activities against five human cancer cells (HL- 60,A-549,SMMC-7721,MCF-7 and SW480) were evaluated with MTS[3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxy methoxyphenyl)-2-(4-sulfopheny)-2H-tetrazolium]assay.Most of the derivatives exhibited better activities compared with tropinone at the concentration of 40 lM.Particularly,derivative 6 showed significant activities with IC50 values of 3.39, 13.59,6.65,13.09 and 12.38 μM respectively against HL-60,A-549,SMMC-7721,MCF-7 and SW480 cells,which suggested more potent activities than that of cis-dichlorodiamineplatinum (DDP).
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| Fund:This work was supported by the Hundred Talents Program of the Chinese Academy of Sciences (CAS),the Youth Innovation Promotion Association,CAS and the Program of Yunling Scholarship. |
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Issue Date: 06 February 2018
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1. A. Silverstein, P. Mugenzi, J. Lule, A. Costas-Chavarri, J. Cancer Policy. 7, 1-3 (2016)
2. K. Strasser-Weippl, Y.C. Chavarri-Guerra, B.L. Bychkovsky, M. Debiasi, P.E. Liedke, E. Soto-Perez-de-Celis, D. Dizon, E. Cazap, G. de Lima Lopes, D. Touya, J.S. Nunes, J. Stlouis, C. Vail, A. Bukowski, P. Ramos-Elias, K. Unger-Saldana, D.F. Brandao, M.E. Ferreyra, S. Luciani, A. Nogueira-Rodrigues, A.F. de Carvalho Calabrich, M.G. Del Carmen, J.A. Rauh-Hain, K. Schmeler, R. Sala, P. E. Goss. Lancet. Oncol. 16, 1405-1438 (2015)
3. J.B. Gibbs, Science 287, 1969-1973 (2000)
4. H. Varmus, Science 312, 1162-1165 (2006)
5. W.G. Kaelin, J. Clin. Invest. 104, 1503-1506 (1999)
6. H. Varmus, H.S. Kumar. Sci. Transl. Med. 5, 175cm2 (2013)
7. M. Gadzikowska, G. Grynkiewicz, Acta Pol. Pharm. 58, 481-492 (2001)
8. L. Melzig, A. Gavryushin, P. Knochel, Org. Lett. 26, 5529-5532 (2007)
9. K.C. Schmitt, J. Zhen, P. Kharkar, M. Mishra, N. Chen, A.K. Dutta, M.E.A. Reith, J. Neurochem. 107, 928-940 (2008)
10. R.H. Kline, S. Izenwasser, J.L. Katz, D.B. Joseph, W.D. Bowen, A.H. Newman, J. Med. Chem. 40, 851-857 (1997)
11. J.L. Katz, G.E. Agoston, K.L. Alling, R.H. Kline, M.J. Forster, W.L. Woolverton, T.A. Kopajtic, A.H. Newman, Psychopharmacology 154, 362-374 (2001)
12. G. Maksay, P. Nemes, Z. Vincze, T. Bíró, Bioorg. Med. Chem. 16, 2086-2092 (2008)
13. R.L. Papke, H.C. Schiff, B.A. Jack, N.A. Horenstein, Neurosci. Lett. 378, 140-144 (2005)
14. K. Sun, Z.D. Guo, Int. J. Pharm. Res. 35, 87-91 (2008)
15. D.I. Lainé, H.B. Xie, N. Buffet, J.J. Foley, P. Buckley, E.F. Webb, K.L. Widdowson, M.R. Palovich, K.E. Belmonte. Bioorg. Med. Chem. Lett. 17, 6066-6069 (2007)
16. R. De Simone, L. Margarucci, V. De Feo, Pharmacologyonline. 1, 70-89 (2008)
17. J.W. Medley, M. Movassaghi, Chem. Commun. 49, 10775-10777 (2013)
18. Y.L. Hsu, P.L. Kuo, W.S. Tzeng, C.C. Lin, Food Chem. Toxicol. 44, 704-713 (2006)
19. D.K. Mahapatra, S.K. Bharti, V. Asati, Eur. J. Med. Chem. 98, 69-114 (2015)
20. A. Modzelewska, C. Pettit, G. Achanta, N.E. Davidson, P. Huang, S.R. Khan, Bioorgan. Med. Chem. 14, 3491-3495 (2006)
21. K.V. Sashidhara, A. Kumar, M. Kumar, J. Sarkar, S. Sinha, Bioorg. Med. Chem. 20, 7205-7211 (2010)
22. C.F. Jin, Y.J. Liang, H.W. He, L.W. Fu, Biomed. Pharmacother. 67, 215-217 (2013)
23. H.J. Zhang, Y. Qian, D.D. Zhu, X.G. Yang, H.L. Zhu, Eur. J. Med. Chem. 46, 4702-4708 (2011)
24. A. Kamal, G. Ramakrishna, P. Raju, A. Viswanath, M.J. Ramaiah, G. Balakishan, M. Pal-Bhadra, Bioorg. Med. Chem. Lett. 20, 4865-4869 (2010)
25. U. Das, J. Alcorn, A. Shrivastav, R.K. Sharma, E. De Clercq, J. Balzarini, J.R. Dimmock, Euro. J. Med. Chem. 42, 71-80 (2007)
26. A. Anantharaman, H. Hemachandran, S. Mohan, D.M. Ayyathan, T. Kumar, D, G.P. Doss C, R. Siva. J. Funct. Foods. 20, 346-357 (2016)
27. A. Anantharaman, B. Subramanian, R. Chandrasekaran, R. Seenivasan, R. Siva, Ind. Crop. Prod. 53, 167-186 (2014)
28. H.P. Chen, Z.Z. Zhao, Z.H. Li, Z.J. Dong, K. Wei, X. Bai, L. Zhang, C.N. Wen, T. Feng, J.K. Liu, ChemistryOpen. 5, 142-149 (2016)
29. L.D. Shao, Y.N. Wu, J. Xu, J. He, Y. Zhao, L.Y. Peng, Y. Li, Y.R. Yang, C.F. Xia, Q.S. Zhao, Nat. Prod. Bioprospect. 4, 181-188 (2014)
30. R. Chu, L.S. Wan, X.R. Peng, M.Y. Yu, Z.R. Zhang, L. Zhou, Z.R. Li, M.H. Qiu, Nat. Prod. Bioprospect. 6, 217-223 (2016)
31. G.R. Zheng, L.P. Dwoskin, A.G. Deaciuc, P.A. Crooks, Bioorg. Med. Chem. Lett. 15, 4463-4466 (2005)
32. D.I. Jung, C.S. Park, Y.H. Kim, D.H. Lee, Y.G. Lee, M. Park, S.K. Choi, Synth. Commun. 31, 3255-3263 (2001)
33. H.N. Pati, U. Das, S. Das, B. Bandy, E. De Clercq, J. Balzarini, M. Kawase, H. Sakagami, J.W. Quail, J.P. Stables, J.R. Dimmock, Eur. J. Med. Chem. 44, 54-62 (2009)
34. M. Suffness, J. Douros. Part A, in:V.T. De Vita Jr., H. Busch (Eds.), Methods in Cancer Research (Academic Press, New York, 1979) vol. 16, p. 84
35. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, J. Natl Cancer Inst. 83, 757-766 (1991)
36. L.J. Reed, H. Muench, Am. J. Hyg. 27, 493-497 (1938) |
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