Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Antiproliferative Activity of Pyridinylcarbonylpyrimidines Against Melanoma Cell Line

  • Ahn, Hye-Mi (Life/Health Division, Korea Institute of Science and Technology) ;
  • Lee, Jun-A (Life/Health Division, Korea Institute of Science and Technology) ;
  • Kim, Hwan (Life/Health Division, Korea Institute of Science and Technology) ;
  • Oh, Chang-Hyun (Life/Health Division, Korea Institute of Science and Technology) ;
  • Lee, So-Ha (Life/Health Division, Korea Institute of Science and Technology) ;
  • Sim, Tae-Bo (Life/Health Division, Korea Institute of Science and Technology) ;
  • Hah, Jung-Mi (Department of Pharmacy, College of Pharmacy, Hanyang University) ;
  • Kim, Dong-Jin (Life/Health Division, Korea Institute of Science and Technology) ;
  • Yoo, Kyung-Ho (Life/Health Division, Korea Institute of Science and Technology)
  • Received : 2011.01.03
  • Accepted : 2011.02.07
  • Published : 2011.04.20
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Abstract

The synthesis of the series of pyrimidinylamines 1a-d and pyrimidinylureas 1e-u bearing a novel pyridinylcarbonylpyrimidine scaffold and their antiproliferative activities against A375 human melanoma cell line were described. Among them, three compounds 1e, 1h, and 1o showed superior antiproliferative activities to Sorafenib ($IC_{50}=5.5{\mu}M$) as a reference compound. In our series, urea compound 1o having 4-chloro-3-trifluoromethyl moiety on the benzene nucleus exhibited very good antiproliferative activity with $IC_{50}$ value of $1.4{\mu}M$.

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References

  1. Gruijl, F. R. Pigment Cell Res. 2003, 16, 591.
  2. Garbe C.; Hauschild, A.; Volkenandt, M.; Schadendorf, D.; Stolz, W.; Reinhold, U.; Kortmann, R. D.; Kettelhack, C.; Frerich, B.; Keilholz, U.; Dummer, R.; Sebastian, G.; Tilgen, W.; Schuler, G.; Mackensen, A.; Kaufmann, R. Melanoma Res. 2007, 17, 393. https://doi.org/10.1097/CMR.0b013e3282f05039
  3. Carlson, J. A.; Ross, J. S.; Slominski, A.; Linette, G.; Mysliborski, J.; Hill, J.; Mihm, M., Jr. J. Am. Acad. Dermatol. 2005, 52, 743. https://doi.org/10.1016/j.jaad.2004.08.034
  4. Buzaid, A. C.; Anderson, C. M. Curr. Oncol. Rep. 2000, 2, 322. https://doi.org/10.1007/s11912-000-0025-9
  5. Middleton, M. R.; Grob, J. J.; Aaronson, N.; Fierlbeck, G.; Tilgen, W.; Seiter, S.; Gore, M.; Aamdal, S.; Cebon, J.; Coates, A.; Dreno, B.; Henz, M.; Schadendorf, D.; Kapp, A.; Weiss, J.; Fraass, U.; Statkevich, P.; Muller, M.; Thatcher, N. J. Clin. Oncol. 2000, 18, 158.
  6. Bedikian, A. Y.; Millward, M.; Pehamberger, H.; Conry, R.; Gore, M.; Trefzer, U.; Pavlick, A. C.; DeConti, R.; Hersh, E. M.; Hersey, P.; Kirkwood, J. M.; Haluska, F. G. J. Clin. Oncol. 2006, 24, 4738. https://doi.org/10.1200/JCO.2006.06.0483
  7. Serrone, L.; Zeuli, M.; Sega, F. M.; Cognetti, F. J. Exp. Clin. Cancer Res. 2000, 19, 21.
  8. Fletcher, W. S.; Daniels, D. S.; Sondak, V. K.; Dana, B.; Townsend, R.; Hynes, H. E.; Hutchins, L. F.; Pancoast, J. R. Am. J. Clin. Oncol. 1993, 16, 359. https://doi.org/10.1097/00000421-199308000-00018
  9. Anderson, C. M.; Buzaid, A. C.; Legha, S. S. Oncology (Williston Park) 1995, 9, 1149.
  10. Grossman, D.; Altieri, D. C. Cancer Metastasis Rev. 2001, 20, 3. https://doi.org/10.1023/A:1013123532723
  11. Hayes, M. T.; Bartley, J.; Parsons, P. G.; Eaglesham, G. K.; Prakash, A. S. Biochemistry 1997, 36, 10646. https://doi.org/10.1021/bi970791q
  12. Franciosi, V.; Cocconi, G.; Michiara, M.; Di Costanzo, F.; Fosser, V.; Tonato, M.; Carlini, P.; Boni, C.; Di Sarra, S. Cancer 1999, 85, 1599. https://doi.org/10.1002/(SICI)1097-0142(19990401)85:7<1599::AID-CNCR23>3.0.CO;2-#
  13. Middleton, M. R.; Lorigan, P.; Owen, J.; Ashcroft, L.; Lee, S. M.; Harper, P.; Thatcher, N. Br. J. Cancer 2000, 82, 1158. https://doi.org/10.1054/bjoc.1999.1056
  14. Gray-Schopfer, V.; Wellbrock, C.; Marais, R. Nature 2007, 445, 851. https://doi.org/10.1038/nature05661
  15. Eton, O.; Legha, S. S.; Bedikian, A. Y.; Lee, J. J.; Buzaid, A. C.; Hodges, C.; Ring, S. E.; Papadopoulos, N. E.; Plager, C.; East, M. J.; Zhan, F.; Benjamin, R. S. J. Clin. Oncol. 2002, 20, 2045. https://doi.org/10.1200/JCO.2002.07.044
  16. Nam, B. S.; Kim, H.; Oh, C.-H.; Lee, S. H.; Cho, S. J.; Sim, T. B.; Hah, J.-M.; Kim, D. J.; Choi, J. H.; Yoo, K. H. Bioorg. Med. Chem. Lett. 2009, 19, 3517. https://doi.org/10.1016/j.bmcl.2009.05.007
  17. Lee, J.; Nam, B. S.; Kim, H.; Oh, C.-H.; Lee, S. H.; Cho, S. J.; Sim, T. B.; Hah, J.-M.; Kim, D. J.; Tae, J.; Yoo, K. H. Bioorg. Med. Chem. Lett. 2010, 20, 5722. https://doi.org/10.1016/j.bmcl.2010.08.010
  18. Li, H.-F.; Lu, T.; Zhu, T.; Jiang, Y.-J.; Rao, S.-S.; Hu, L.-Y.; Xin, B.-T.; Chen, Y.-D. Eur. J. Med. Chem. 2009, 44, 1240. https://doi.org/10.1016/j.ejmech.2008.09.016
  19. Aquila, B.; Cook, D. J.; Johnstone, C.; Lee, S.; Lyne, P.; Rudge, D. A.; Vasbinder, M.; Wang, H. WO 2008/020203; WO 2008/068507.
  20. Wilhelm, S. M.; Adnane, L.; Newell, P.; Villanueva, A.; Llovet, J. M.; Lynch, M. Mol. Cancer Ther. 2008, 7, 3129. https://doi.org/10.1158/1535-7163.MCT-08-0013
  21. Remuinan, M.; Gonzalez, J. J.; Del Pozo, C.; Francesch, A.; Cuevas, C.; Munt, S.; Manzanares, I. WO 2003/006457.
  22. Johns, B. A.; Gudmundsson, K. S.; Turner, E. M.; Allen, S. H.; Samano, V. A.; Ray, J. A.; Freeman, G. A.; Boyd, F. L.; Sexton, C. J.; Selleseth, D. W.; Creech, K. L.; Moniri, K. R. Bioorg. Med. Chem. 2005, 13, 2397. https://doi.org/10.1016/j.bmc.2005.01.044
  23. Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652. https://doi.org/10.1021/jo060847z
  24. Nagata, T.; Masuda, K.; Maeno, S.; Miura, I. Pest Manag. Sci. 2004, 60, 399. https://doi.org/10.1002/ps.828
  25. Van Rossom, W.; Maes, W.; Kishore, L.; Ovaere, M.; Van Meervelt, L.; Dehaen, W. Org. Lett. 2008, 10, 585. https://doi.org/10.1021/ol702864y

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