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Design, Synthesis, and Preliminary Cytotoxicity Evaluation of New Diarylureas and Diarylamides Possessing 1,3,4-Triarylpyrazole Scaffold

  • Received : 2012.03.15
  • Accepted : 2012.06.18
  • Published : 2012.09.20

Abstract

A series of new diarylureas and diarylamides possessing 1,3,4-triarylpyrazole scaffold was synthesized and their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-60 cell line panel were tested. Compounds 9, 11, 12, 14, and 17-21 showed superior potency against A375P to Sorafenib. Over the NCI-60 cancer cell line panel, compound 14 possessing a methoxy group, amide linker, and 4-chloro-3-(trifluoromethyl)phenyl terminal ring showed the highest potency and broad-spectrum anticancer activity. Compound 13 showed high selectivity towards leukemia subpanel over other cancer types.

Keywords

References

  1. WHO website: http://www.who.int/mediacentre/factsheets/fs297/ en/.
  2. Jung, M.-H.; Oh, C.-H. Bull. Korean Chem. Soc. 2008, 29, 2231. https://doi.org/10.5012/bkcs.2008.29.11.2231
  3. 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
  4. 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
  5. Song, D.-Q.; Du, N.-N.; Wang, Y.-M.; He, W.-Y.; Jiang, E.-Z.; Cheng, S.-X.; Wang, Y.-X.; Li, Y.-H.; Wang, Y.-P.; Li, X.; Jiang, J.-D. Bioorg. Med. Chem. 2009, 17, 3873. https://doi.org/10.1016/j.bmc.2009.04.022
  6. 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
  7. 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
  8. 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
  9. El-Deeb, I. M.; Lee, S. H. Bioorg. Med. Chem. 2010, 18, 3860. https://doi.org/10.1016/j.bmc.2010.04.037
  10. Yao, P.; Zhai, X.; Liu, D.; Qi, B. H.; Tan, H. L.; Jin, Y. C.; Gong, P. Arch. Pharm. Chem. Life Sci. 2010, 343, 17.
  11. 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
  12. 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
  13. El-Gamal, M. I.; Oh, C.-H. Bull. Korean Chem. Soc. 2012, 33, 1571. https://doi.org/10.5012/bkcs.2012.33.5.1571
  14. 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
  15. Wilhelm, S.; Carter, C.; Lynch, M.; Lowinger, T.; Dumas, J.; Smith, R. A.; Schwartz, B.; Simantov, R.; Kelley, S. Nat. Rev. Drug Discov. 2006, 5, 835. https://doi.org/10.1038/nrd2130
  16. DGNews website: http://www.pslgroup.com/news/content.nsf/ medicalnews/852571020057CCF685257384005A45B1?Open Document&id=&count=10.
  17. Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Disc. 2002, 1, 493. https://doi.org/10.1038/nrd839
  18. Dean, D. K.; Takle, A. K.; Wilson, D. M. WO 2003022832 A1.
  19. El-Gamal, M. I.; Oh, C.-H. Bull. Korean Chem. Soc. 2011, 32, 821. https://doi.org/10.5012/bkcs.2011.32.3.821
  20. NCI website: www.dtp.nci.nih.gov.

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