Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Antiproliferative Activity of New Aminoisoquinolinylurea Derivatives against Melanoma Cell Line

  • Cho, Hye Jung (Chemical Kinomics Research Center, Korea Institute of Science and Technology) ;
  • El-Gamal, Mohammed I. (Center for Biomaterials, Korea Institute of Science and Technology) ;
  • Oh, Chang-Hyun (Center for Biomaterials, Korea Institute of Science and Technology) ;
  • Lee, So Ha (Chemical Kinomics Research Center, Korea Institute of Science and Technology) ;
  • Kim, Garam (College of Pharmacy, Chosun University) ;
  • Hong, Jun Hee (College of Pharmacy, Chosun University) ;
  • Choi, Hong Seok (College of Pharmacy, Chosun University) ;
  • Yoo, Kyung Ho (Chemical Kinomics Research Center, Korea Institute of Science and Technology)
  • Received : 2012.07.28
  • Accepted : 2012.08.08
  • Published : 2012.11.20
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Abstract

A series of new diarylureas possessing aminoisoquinoline scaffold was synthesized, and their in vitro antiproliferative activity against A375P human melanoma cell line was tested. Compounds 1d, 1l, 1n, 1p, 1q, and 1t showed superior potency against A375P to Sorafenib. The highest potency was shown by compound 1p possessing 3,5-bis(trifluoromethyl)phenyl terminal ring with $IC_{50}$ value of $0.41{\mu}M$.

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References

  1. 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
  2. Balch, C. M.; Buzaid, A. C.; Soong, S. J.; Atkins, M. B.; Cascinelli, N.; Coit, D. G.; Fleming, I. D.; Gershenwald, J. E.; Houghton, A., Jr.; Kirkwood, J. M.; McMasters, K. M.; Mihm, M. F.; Morton, D. L.; Reintgen, D. S.; Ross, M. I.; Sober, A.; Thompson, J. A.; Thompson, J. F. J. Clin. Oncol. 2001, 19, 3635. https://doi.org/10.1200/JCO.2001.19.16.3635
  3. Lee, M. L.; Tomsu, K.; Von Eschen, K. B. Melanoma Res. 2000, 10, 81.
  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.; 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
  8. 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
  9. Jung, M.-H.; Kim, H.; Choi, W.-K.; El-Gamal, M. I.; Park, J.-H.; Yoo, K. H.; Sim, T. B.; Lee, S. H.; Baek, D.; Hah, J.-M.; Cho, J.- H.; Oh, C.-H. Bioorg. Med. Chem. Lett. 2009, 19, 6538. https://doi.org/10.1016/j.bmcl.2009.10.051
  10. Choi, W.-K.; Oh, C.-H. Bull. Korean Chem. Soc. 2009, 30, 2027. https://doi.org/10.5012/bkcs.2009.30.9.2027
  11. Kim, H. J.; Jung, M.-H.; Kim, H.; El-Gamal, M. I.; Sim, T. B.; Lee, S. H.; Hong, J. H.; Hah, J.-M.; Cho, J.-H.; Choi, J. H.; Yoo, K. H.; Oh, C.-H. Bioorg. Med. Chem. Lett. 2010, 20, 413. https://doi.org/10.1016/j.bmcl.2009.08.005
  12. Lee, J.; Kim, H.; Yu, H.; Chung, J. Y.; Oh, C.-H.; Yoo, K. H.; Sim, T.; Hah, J.-M. Bioorg. Med. Chem. Lett. 2010, 20, 1573. https://doi.org/10.1016/j.bmcl.2010.01.064
  13. Yu, H.; Jung, Y.; Kim, H.; Lee, J.; Oh, C.-H.; Yoo, K. H.; Sim, T.; Hah, J.-M. Bioorg. Med. Chem. Lett. 2010, 20, 3805. https://doi.org/10.1016/j.bmcl.2010.04.039
  14. 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
  15. El-Gamal, M. I.; Jung, M.-H.; Lee, W. S.; Sim, T.; Yoo, K. H.; Oh, C.-H. Eur. J. Med. Chem. 2011, 46, 3218. https://doi.org/10.1016/j.ejmech.2011.04.031
  16. Choi, W.-K.; El-Gamal, M. I.; Choi, H. S.; Baek, D.; Oh, C.-H. Eur. J. Med. Chem. 2011, 46, 5754.
  17. Kim, H. J.; Cho, H. J.; Kim, H.; El-Gamal, M. I.; Oh, C.-H.; Lee, S. H.; Sim, T.; Hah, J.-M.; Yoo, K. H. Bioorg. Med. Chem. Lett. 2012, 22, 3269. https://doi.org/10.1016/j.bmcl.2012.03.020
  18. Jung, M.-H.; El-Gamal, M. I.; Abdel-Maksoud, M. S.; Sim, T.; Yoo, K. H.; Oh, C.-H. Bioorg. Med. Chem. Lett. 2012, 22, 4362. https://doi.org/10.1016/j.bmcl.2012.05.004
  19. El-Gamal, M. I.; Oh, C.-H. Bull. Korean Chem. Soc. 2012, 33, 1571. https://doi.org/10.5012/bkcs.2012.33.5.1571
  20. Gamage, S. A.; Spicer, J. A.; Rewcastle, G. W.; Milton, J.; Sohal, S.; Dangerfield, W.; Mistry, P.; Vicker, N.; Charlton, P. A.; Denny, W. A. J. Med. Chem. 2002, 45, 740. https://doi.org/10.1021/jm010330+

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