Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of rigid analogues of 2,4,6-trisubstituted pyridine containing 5,6-dihydrobenzo[h]quinoline moiety

Bulletin of the Korean Chemical Society

Volumn 32, Issue 1, 2011, Pages 303-306

  Jeong, Byeong Seon ^a   Choi, Hoyoung ^a   Thapa, Pritam ^a   Karki, Radha ^a   Lee, Eunyoung ^b   Nam, Jung Min ^b   Na, Younghwa ^c   Ha, Eun Mi ^c   Kwon, Youngjoo ^a   Lee, Eung Seok ^a  

^a Yeungnam University   (South Korea)

^b Ewha Womans University   (South Korea)

^c Catholic University of Daegu   (South Korea)

Author keywords

2,4,6 Trisubstituted pyridine; 5,6 Dihydrobenzo h quinoline; Cytotoxicity; Rigid analog; Topoisomerase inhibitor

Indexed keywords

EID: 78951477341     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.1.303     Document Type: Article

References (24)

1. Wang, J. C. Annu. Rev. Biochem. 1996, 65, 635.
2. Nitiss, J. L. Biochim. Biophys. Acta 1998, 1400, 63.
3. Holden, J. A. Curr. Med. Chem.-Anticancer Agent 2001, 1, 1.
4. Topcu, Z. J. Clin. Pharm. Ther. 2001, 26, 405.
5. (a) Zhao, L. X.; Kim, T. S.; Ahn, S. H.; Kim, T. H.; Kim, E. K.; Cho, W. J.; Choi, H. S.; Lee, C. S.; Kim, J. A.; Jeong, T. C.; Chang, C.-J.; Lee, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 2659.
6. (b) Zhao, L. X.; Moon, Y. S.; Basnet, A.; Kim, E. K.; Jahng, Y.; Park, J. G.; Jeong, T. C.; Cho, W. J.; Choi, S. U.; Lee, C. O.; Lee, S. Y.; Lee, C. S.; Lee, E. S. Bioorg. Med. Chem. Lett. 2004, 14, 1333.
7. (c) Zhao, L. X.; Sherchan, J.; Park, J. K.; Jahng, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. Arch. Pharm. Res. 2006, 29, 1091.
8. (d) Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. Bioorgan. Med. Chem. 2007, 15, 4351.
9. (e) Son, J. K.; Zhao, L. X.; Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, T. C.; Jeong, B. S.; Lee, C. S.; Lee, E. S. Eur. J. Med. Chem. 2008, 43, 675.
10. (f) Thapa, P.; Karki, R.; Basnet, A.; Thapa, U.; Choi, H. Y.; Na, Y.; Jahng, Y., Lee, C. S.; Kwon, Y.; Jeong, B. S.; Lee, E. S. Bull. Korean Chem. Soc. 2008, 29, 1605.
11. (g) Basnet, A.; Thapa, P.; Karki, R.; Choi, H. Y.; Choi, J. H.; Yun, M.; Jeong, B. S.; Jahng, Y.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, C. S.; Lee, E.-S. Bioorg. Med. Chem. Lett. 2010, 20, 42.
12. (h) Thapa, P.; Karki, R.; Thapa, U.; Jahng, Y.; Jung, M. J.; Nam, J. M.; Na, Y.; Kwon, Y.; Lee, E.-S. Bioorg. Med. Chem. 2010, 18, 377.
13. (i) Thapa, P.; Karki, R.; Choi, H. Y.; Choi, J. H.; Yun, M.; Jeong, B. S.; Jung, M. J.; Nam, J. M.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, E.-S. Bioorg. Med. Chem. 2010, 18, 2245.
14. (j) Karki, R.; Thapa, P.; Kang, M. J.; Jeong, T. C.; Nam, J. M.; Kim, H.-L.; Na, Y.; Cho, W. J.; Kwon, Y.; Lee, E.-S. Bioorg. Med. Chem. 2010, 18, 3066.
15. (k) Karki, R.; Thapa, P.; Kwon, Y.; Lee, E.-S. Bull. Korean Chem. Soc. 2010, 31, 1747.
16. Andaloussi, M.; Moreau, E.; Masurier, N.; Lacroix, J.; Gaudreault, R. C.; Chezal, J. M.; Laghdach, A. E.; Canitrot, D.; Debiton, E.; Teulade, J. C.; Chavignon, O. Eur. J. Med. Chem. 2008, 43, 2505.
17. Chackal, S.; Houssin, R.; Pommery, N.; Henischart, J. P. J. Enzym. Inhib. Med. Chem. 2003, 18, 95.
18. El-Gazzar, A. B. A.; Aly, A. S.; Zaki, M. E. A.; Hafez, H. N. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2119.
19. Fukuda, M.; Nishio, K.; Kanzawa, F.; Ogasawara, H.; Ishida, T.; Arioka, H.; Bonjanowski, K.; Oka, M.; Saijo, N. Cancer Res. 1996, 56, 789.
20. Kang, D. H.; Kim, J. S.; Jung, M. J.; Lee, E. S.; Jahng, Y.; Kwon, Y.; Na, Y. Bioorg. Med. Chem. Lett. 2008, 18, 1520.
21. Jahng, Y.; Zhao, L. X.; Moon, Y. S.; Basnet, A.; Kim, E. K.; Chang, H. W.; Ju, H. K.; Jeong, T. C.; Lee, E. S. Bioorg. Med. Chem. Lett. 2004, 14, 2559.
22. Kröhnke, F. Synthesis 1976, 1.
23. Kröhnke, F. Angew. Chem. Int. Ed. 1963, 2, 380.
24. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3.