Synthesis, cytotoxic activities and DNA binding properties of β-carboline derivatives

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 4740-4745

  Chen, Zhiyong ^a   Cao, Rihui ^a   Yu, Liang ^a   Shi, Buxi ^a   Sun, Jie ^b   Guo, Liang ^b   Ma, Qin ^b   Yi, Wei ^a   Song, Xiao ^a   Song, Huacan ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b Xinjiang Huashidan Pharmaceutical Co Ltd   (China)

Author keywords

Carboline; Cytotoxic; Intercalating; Synthesis; Tm

Indexed keywords

1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (2 DIETHYLAMINO)ETHYL]AMINOMETHYL 9 (3 PHENYL)PROPYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (2 DIETHYLAMINO)ETHYL]AMINOMETHYL 9 METHYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (2 DIETHYLAMINO)ETHYL]AMINOMETHYL 9 N BUTYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIETHYLAMINO)PROPYL]; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIETHYLAMINO)PROPYL]AMINOMETHYL 9 METHYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIETHYLAMINO)PROPYL]AMINOMETHYL 9 N BUTYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIMETHYLAMINO)PROPYL]; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 (3 PHENYL)PROPYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 METHYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (3 DIMETHYLAMINO)PROPYL]AMINOMETHYL 9 N BUTYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (4 DIETHYLAMINO)BUTYL]AMINOMETHYL 9 (3 PHENYL)PROPYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (4 DIETHYLAMINO)BUTYL]AMINOMETHYL 9 METHYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3 [N (4 DIETHYLAMINO)BUTYL]AMINOMETHYL 9 N BUTYL BETA CARBOLINE; 1 (3,4,5 TRIMETHOXY)PHENYL 3-[N (3 DIETHYLAMINO)PROPYL]AMINOMETHYL 9 (3 PHENYL)PROPYL BETA CARBOLINE; ALKYL ARYL ETHER; BETA CARBOLINE DERIVATIVE; CISPLATIN; PACLITAXEL; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG DNA BINDING; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; STRUCTURE ACTIVITY RELATION;

ANIMALS; CARBOLINES; CATTLE; DNA; SPECTROMETRY, FLUORESCENCE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77957833612     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.037     Document Type: Article

References (34)

1. R. Cao, W. Peng, Z. Wang, and A. Xu Curr. Med. Chem. 14 2007 479 500
2. S.P. Hollinshead, M.L. Trudell, P. Skolnick, and J.M. Cook J. Med. Chem. 33 1990 1062 1069
3. M.S. Allen, A.J. LaLoggia, L.J. Dorn, M.J. Martin, G. Costantino, T.J. Hagen, K.F. Koehler, P. Skolnick, and J.M. Cook J. Med. Chem. 35 1992 4001 4010
4. E.D. Cox, H. Diaz-Arauzo, Q. Huang, M.S. Reddy, C. Ma, B. Harris, R. McKernan, P. Skolnick, and J.M. Cook J. Med. Chem. 41 1998 2537 2552
5. R.A. Glennon, M. Dukat, B. Grella, S.S. Hong, L. Costantino, M. Teitler, C. Smith, C. Egan, K. Davis, and M.V. Mattson Drug. Alcohol. Depend. 60 2000 121 132
6. B. Grella, M. Teitler, C. Smith, K. Herrick-Davis, and R.A. Glennon Bioorg. Med. Chem. Lett. 13 2003 4421 4425
7. A.F.M. Abdel-Fattah, K. Matsumoto, H.A.F. Gammaz, and H. Watanabe Pharmacol. Biochem. Behav. 52 1995 421 426
8. S.M. Husbands, R.A. Glennon, S. Gorgerat, R. Gough, R. Tyacke, J. Crosby, D.J. Nutt, J.W. Lewis, and A.L. Hudson Drug. Alcohol. Depend. 64 2001 203 208
9. R.A. Glennon, B. Grella, R.J. Tyacke, A. Lau, J. Westaway, and A. Hudson Bioorg. Med. Chem. Lett. 14 2004 999 1002
10. A. Miralles, S. Esteban, A. Sastre-Coll, D. Moranta, V.J. Asensio, and J.A. Garcia-Sevilla Eur. J. Pharmacol. 518 2005 234 242
11. J. Ishida, H.K. Wang, K.F. Bastow, C.Q. Hu, and K.H. Lee Bioorg. Med. Chem. Lett. 9 1999 3319 3324
12. S. Xiao, W. Lin, C. Wang, and M. Yang Bioorg. Med. Chem. Lett. 11 2001 437 441
13. Y.C. Shen, C.Y. Chen, P.W. Hsieh, C.Y. Duh, Y.M. Lin, and C.L. Ko Chem. Pharm. Bull. 53 2005 32 36
14. A.M. Deveau, M.A. Labroli, C.M. Dieckhaus, M.T. Barthen, K.S. Smith, and T.L. Macdonald Bioorg. Med. Chem. Lett. 11 2001 1251 1255
15. M. Zhao, L. Bi, W. Wang, C. Wang, M. Baudy-Floc'h, J. Ju, and S. Peng Bioorg. Med. Chem. 14 2006 6998 7010
16. A.S.N. Formagio, L.T.D. Dusman, M.A. Foglio, C. Madjarof, J.E. Carvalho, W.F. Costa, F.P. Cardoso, and M.H. Sarragiotto Bioorg. Med. Chem. 16 2008 9660 9667
17. J. Wu, M. Zhao, K. Qian, K.-H. Lee, S. Morris-Natschke, and S. Peng Eur. J. Med. Chem. 44 2009 4153 4161
18. Y. Boursereau, and I. Coldham Bioorg. Med. Chem. Lett. 14 2004 5841 5844
19. K. Hayashi, M. Nagao, and T. Sugimura Nucleic. Acids. Res. 4 1977 3679 3685
20. Y. Song, J. Wang, S.F. Teng, D. Kesuma, Y. Deng, J. Duan, J.H. Wang, R.Z. Qi, and M.M. Sim Bioorg. Med. Chem. Lett. 12 2002 1129 1132
21. Y. Song, D. Kesuma, J. Wang, Y. Deng, J. Duan, J.H. Wang, and R.Z. Qi Biochem. Biophys. Res. Commun. 317 2004 128 132
22. Y. Li, F. Liang, W. Jiang, F. Yu, R. Cao, Q. Ma, X. Dai, J. Jiang, Y. Wang, and S. Si Cancer. Biol. Ther. 6 2007 1193 1199
23. A.C. Castro, L.C. Dang, F. Soucy, L. Grenier, H. Mazdiyasni, M. Hottelet, L. Parent, C. Pien, V. Palombella, and J. Adams Bioorg. Med. Chem. Lett. 13 2003 2419 2422
24. J.I. Trujillo, M.J. Meyers, D.R. Anderson, S. Hegde, M.W. Mahoney, W.F. Vernier, I.P. Buchler, K.K. Wu, S. Yang, S.J. Hartmann, and D.B. Reitz Bioorg. Med. Chem. Lett. 17 2007 4657 4663
25. P.A. Barsanti, W. Wang, Z. Ni, D. Duhl, N. Brammeier, and E. Martin Bioorg. Med. Chem. Lett. 20 2010 157 160
26. R. Cao, W. Peng, H. Chen, Y. Ma, X. Liu, X. Hou, H. Guan, and A. Xu Biochem. Biophys. Res. Commun. 338 2005 1557 1563
27. H. Guan, X. Liu, W. Peng, R. Cao, Y. Ma, H. Chen, and A. Xu Biochem. Biophys. Res. Commun. 342 2006 894 901
28. Q. Chen, R. Chao, H. Chen, X. Hou, H. Yan, S. Zhou, W. Peng, and A. Xu Int. J. Cancer. 114 2004 675 682
29. R. Cao, Q. Chen, X. Hou, H. Chen, H. Guan, Y. Ma, W. Peng, and A. Xu Bioorg. Med. Chem. 12 2004 4613 4623
30. R. Cao, W. Peng, H. Chen, X. Hou, H. Guan, Q. Chen, Y. Ma, and A. Xu Eur. J. Med. Chem. 40 2005 249 257
31. R. Cao, H. Chen, W. Peng, Y. Ma, X. Hou, H. Guan, X. Liu, and A. Xu Eur. J. Med. Chem. 40 2005 991 1001
32. H. Guan, H. Chen, W. Peng, Y. Ma, R. Cao, X. Liu, and A. Xu Eur. J. Med. Chem. 41 2006 1167 1179
33. R. Cao, W. Yi, Q. Wu, X. Guan, M. Feng, C. Ma, Z. Chen, H. Song, and W. Peng Bioorg. Med. Chem. Lett. 18 2008 6558 6561
34. Q. Wu, R. Cao, M. Feng, X. Guan, C. Ma, J. Liu, H. Song, and W. Peng Eur. J. Med. Chem. 44 2009 533 540