Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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2,6-Dithienyl-4-arylpyridines: Synthesis, Topoisomerase I and II Inhibition and Structure-activity Relationship

  • Published : 2008.08.20
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References

  1. Wang, J. C. Annu. Rev. Biochem. 1996, 65, 635 https://doi.org/10.1146/annurev.bi.65.070196.003223
  2. Pommier, Y. Biochimie 1998, 80, 255 https://doi.org/10.1016/S0300-9084(98)80008-4
  3. Redinbo, M. R.; Stewart, L.; Kuhn, P.; Champoux, J. J.; Hol, W. G. Science 1998, 279, 504
  4. Chen, A. Y.; Liu, L. F. Annu. Rev. Pharmacol. Toxicol. 1994, 34, 191 https://doi.org/10.1146/annurev.pa.34.040194.001203
  5. Kellner, U.; Rudolph, P.; Parwaresch, R. Onkologie 2000, 23, 424 https://doi.org/10.1159/000027205
  6. Singh, S. K.; Ruchelman, A. L.; Li, T. K.; Liu, A.; Liu, L. F.; Lavoie, E. J. J. Med. Chem. 2003, 46, 2254 https://doi.org/10.1021/jm020498a
  7. Mukkala, V. M.; Helenius, M.; Hemmila, I.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 1361 https://doi.org/10.1002/hlca.19930760323
  8. Mukkala, V. M.; Kwiatkowski, M.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 893 https://doi.org/10.1002/hlca.19930760213
  9. Lowe, G.; Droz, A. S.; Park, J. J.; Weaver, G. W. Bioorg. Chemistry 1999, 27, 477 https://doi.org/10.1006/bioo.1999.1152
  10. Jennette, K.; Lippard, S. J.; Vassiliades, G.; Bauer, W. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 3839 https://doi.org/10.1073/pnas.71.10.3839
  11. Liu, H. Q.; Cheung, T. C.; Peng, S. M.; Che, C. M. J. Chem. Soc., Chem. Commun. 1995, 1787
  12. McCoubrey, A.; Latham, H. C.; Cook, P. R.; Rodger, A.; Lower, G. FEBS Letters 1996, 380, 73 https://doi.org/10.1016/0014-5793(95)01537-X
  13. Vliet, P. M. V.; Toekimin, M. S.; Haasnoot, J. G.; Reedijk, J.; Nováková, O.; Vrána, O.; Brabec, V. Inorg. Chim. Acta 1995, 231, 57 https://doi.org/10.1016/0020-1693(94)04320-U
  14. Carter, P. J.; Cheng, C. C.; Thorp, H. H. J. Am. Chem. Soc. 1998, 120, 632 https://doi.org/10.1021/ja9729589
  15. Lowe, G.; Droz, A. S.; Vilaivan, T.; Weaver, G. W.; Tweedale, L.; Pratt, J. M.; Rock, P.; Yardley, V.; Croft, S. L. J. Med. Chem. 1999, 42, 999 https://doi.org/10.1021/jm981074c
  16. Kim, D. S. H. L.; Ashendel, C. L.; Zhou, Q.; Chang, C.-T.; Lee, E. S.; Chang, C.-J. Bioorg. Med. Chem. Lett. 1998, 8, 2695 https://doi.org/10.1016/S0960-894X(98)00468-5
  17. Xu, W. C.; Zhou, Q.; Ashendel, C. L.; Chang, C.-T.; Chang, C.-J. Bioorg. Med. Chem. Lett. 1999, 9, 2279 https://doi.org/10.1016/S0960-894X(99)00375-3
  18. Zhao, L. X.; Kim, T. S.; Ahn, S. H.; Kim, T. H.; Kim, E.-k.; Cho, W. J.; Choi, H.; Lee, C. S.; Kim, J. A.; Jeong, T. C.; Chang, C.-j.; Lee, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 2659 https://doi.org/10.1016/S0960-894X(01)00531-5
  19. Zhao, L.-X.; Moon, Y. S.; Basnet, A.; Kim, E.-K.; Cho, W.-J.; 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 https://doi.org/10.1016/j.bmcl.2003.11.084
  20. 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 https://doi.org/10.1007/BF02969297
  21. Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, B.-S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. Bioorg. Med. Chem. 2007, 15, 4351 https://doi.org/10.1016/j.bmc.2007.04.047
  22. 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 https://doi.org/10.1016/j.ejmech.2007.05.002
  23. Fukuda, M.; Nishio, K.; Kanzawa, F.; Ogasawara, H.; Ishida, T.; Arioka, H.; Bojanowski, K.; Oka, M.; Saijo, N. Cancer Res. 1996, 56, 789
  24. Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94 690 https://doi.org/10.1002/cber.19610940317
  25. Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 698 https://doi.org/10.1002/cber.19610940318
  26. Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 707 https://doi.org/10.1002/cber.19610940319
  27. Krohnke, F. Angew. Chem. Int. Ed. 1963, 2, 380 https://doi.org/10.1002/anie.196303801
  28. Kröhnke, F. Synthesis 1976, 1

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