Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Antiproliferative Activities of 1-Substituted-3-(3-chloro-5-methoxyphenyl)-4-pyridinylpyrazole Derivatives Against Melanoma Cell Line

  • Choi, Won-Kyoung (Biomaterials Research Center, Korea Institute of Science and Technology) ;
  • Oh, Chang-Hyun (Biomaterials Research Center, Korea Institute of Science and Technology)
  • Published : 2009.09.20
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Abstract

The synthesis of a new series of diarylureas and amides having a 1-substituted-3-(3-chloro-5-methoxyphenyl)-4- pyridinylpyrazole scaffold is reported here. The in vitro antiproliferative activities of these diaryl derivatives against human melanoma cell line A375 were tested and the effect of substituents on the phenyl ring was investigated. Most of the newly synthesized compounds generally showed superior or similiar activity against A375 to Sorafenib. Among these compounds, IId, IIg and IIh showed excellent activity against A375 compared to Sorafenib.

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References

  1. Atallah, E.; Flaherty, L. Curr. Treat. Options Oncol. 2005, 6, 185 https://doi.org/10.1007/s11864-005-0002-5
  2. Barth, A.; Wanek, L. A.; Morton, D. L. J. Am. Coll. Surg. 1995, 181, 193
  3. Anderson, C. M.; Buzaid, A. C.; Legha, S. S. Oncol. (Williston Park) 1995, 9, 1149
  4. Gray-Schopfer, V.; Wellbrock, C.; Marais, R. Nature 2007, 445, 851 https://doi.org/10.1038/nature05661
  5. Garbe, C.; Eigentler, T. K. Melanoma Res. 2007, 17, 117 https://doi.org/10.1097/CMR.0b013e328042bb36
  6. Koon, H. B.; Atkins, M. B. Expert Rev. Anticancer Ther. 2007, 7, 79 https://doi.org/10.1586/14737140.7.1.79
  7. Wilhelm, S. M.; Carter, C.; Tang, L.; Wilkie, D.; Mcnabola, A.; Rong, H. Cancer Res. 2004, 64, 7099 https://doi.org/10.1158/0008-5472.CAN-04-1443
  8. Strumberg, D.; Richly, H.; Hilger, R. A.; Schleucher, N.; Korfee, S. J. Clin. Oncol. 2005, 23, 965 https://doi.org/10.1200/JCO.2005.06.124
  9. Clark, J. W.; Eder, J. P.; Ryan, D.; Lathia, C.; Lenz, H. J. Clin. Cancer Res. 2005, 11, 5472 https://doi.org/10.1158/1078-0432.CCR-04-2658
  10. Hirte, H. W.; Moore, M.; Siu, L.; Oza, A.; Hotte, S. J. Ann. Oncol. 2005, 16, 1688 https://doi.org/10.1093/annonc/mdi310
  11. Strumberg, D.; Voliotis, D.; Moller, J. G.; Hilger, R. A.; Richly, H.; Kredtke, S. Int. J. Clin. Pharmacol. Ther. 2002, 40, 580 https://doi.org/10.5414/CPP40580
  12. Richly, H.; Kupsh, P.; Passage, K.; Grubert, M.; Voigtmann, R.; Schwartz, B. Int. J. Clin. Pharmacol. Ther. 2004, 42, 650 https://doi.org/10.5414/CPP42650
  13. Smith, R. A.; Barbosa, J.; Blum, C. L.; Bobko, M. A.; Caringal, Y. V.; Dally, R. Bioorg. Med. Chem. Lett. 2001, 11, 2775 https://doi.org/10.1016/S0960-894X(01)00571-6
  14. Wood, J. E.; Wild, H; Rogers, D. H.; Lyons, J.; Katz, M. E.; Caringal, Y. V. PCT Pat. Appl. WO 98052559, May 23, 1997
  15. Bankston, D.; Dumas, J.; Natero, R.; Riedl, D. R.; Monahan, M.-K. Org. Proc. Res. Dev. 2002, 6, 777 https://doi.org/10.1021/op020205n
  16. Khire, U. R.; Bankston, D.; Barbosa, J.; Brittelli, D. R.; Caringal, Y.; Carlson, R. Bioorg. Med. Chem. Lett. 2004, 14, 783 https://doi.org/10.1016/j.bmcl.2003.11.041
  17. Wan, P. T. C.; Garnett, M. J.; Roe, S. M.; Lee, S.; Niculescudunaz, D. Cell 2004, 116, 855 https://doi.org/10.1016/S0092-8674(04)00215-6
  18. Eisen, T.; Ahmad, T.; Flaherty, K. T.; Gore, M.; Kaye, S.; Marais, R.; Gibbens, I.; Hackett, S.; James, M.; Schuchter, L. M.; Nathanson, K. L.; Xia, C.; Simantov, R.; Schwartz, B.; Poulin-Costello, M.; O'Dwyer, P. J.; Ratain, M. J. Br. J. Cancer 2006, 95, 581 https://doi.org/10.1038/sj.bjc.6603291

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