DOI QR코드

DOI QR Code

Synthesis and Preliminary Cytotoxicity Evaluation of New Diarylamides and Diarylureas Possessing 2,3-Dihydropyrrolo[3,2-b]quinoline Scaffold

  • Kim, Hyun-Jin (Center for Biomaterials, Korea Institute of Science and Technology) ;
  • El-Gamal, Mohammed I. (Center for Biomaterials, Korea Institute of Science and Technology) ;
  • Lee, Yong Sup (Department of Pharmaceutical Science, College of Pharmacy & Department of Life and Nanopharmaceutical Science, Kyung Hee University) ;
  • Oh, Chang-Hyun (Center for Biomaterials, Korea Institute of Science and Technology)
  • Received : 2013.05.08
  • Accepted : 2013.05.31
  • Published : 2013.08.20

Abstract

A new series of diarylamides and diarylureas having 2,3-dihydropyrrolo[3,2-b]quinoline scaffold was synthesized. Their in vitro antiproliferative activities were tested over NCI-60 cancer cell lines of nine different cancer types. Some target compounds showed good inhibition percentages over different cell lines. Among all the target compounds, compound 1f possessing 6,7-dimethoxy-2,3-dihydropyrrolo[3,2-b]quinoline nucleus, amide linker, and 4-chloro-3-(trifluoromethyl)phenyl terminal ring showed high selectivity against MCF7 and MDA-MB-468 breast cancer cell lines more than the other tested cell lines. Its inhibition percentages at $10{\mu}M$ concentration over those two cell lines were 84.97% and 87.13%, respectively.

Keywords

References

  1. http://www.cancer.org/acs/groups/content/@epidemiologysurveilance/documents/document/acspc- 031941.pdf
  2. http://www.who.int/mediacentre/factsheets/fs297/en/
  3. Jung, M.-H.; Oh, C.-H. Bull. Korean Chem. Soc. 2008, 29, 2231. https://doi.org/10.5012/bkcs.2008.29.11.2231
  4. 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
  5. 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
  6. 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
  7. Choi, W.-K.; Oh, C.-H. Bull. Korean Chem. Soc. 2009, 30, 2027. https://doi.org/10.5012/bkcs.2009.30.9.2027
  8. 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
  9. 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
  10. 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
  11. 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.
  12. 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
  13. Choi, W.-K.; El-Gamal, M. I.; Choi, H. S.; Baek, D.; Oh, C.-H. Eur. J. Med. Chem. 2011, 46, 5754. https://doi.org/10.1016/j.ejmech.2011.08.013
  14. 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
  15. El-Gamal, M. I.; Oh, C.-H. Bull. Korean Chem. Soc. 2012, 33, 1571. https://doi.org/10.5012/bkcs.2012.33.5.1571
  16. 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
  17. Choi, W.-K.; El-Gamal, M. I.; Choi, H. S.; Hong, J. H.; Baek, D.; Choi, K.; Oh, C.-H. Bull. Korean Chem. Soc. 2012, 33, 2991. https://doi.org/10.5012/bkcs.2012.33.9.2991
  18. Cho, H. J.; El-Gamal, M. I.; Oh, C.-H.; Kim, G.; Hong, J. H.; Choi, H. S.; Yoo; K. H. Bull. Korean Chem. Soc. 2012, 33, 3635. https://doi.org/10.5012/bkcs.2012.33.11.3635
  19. 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
  20. DGNews website: http://www.pslgroup.com/news/content.nsf/ medicalnews/852571020057CCF685257384005A45B1?Open Document&id=&count=10.
  21. Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Discov. 2002, 1, 493. https://doi.org/10.1038/nrd839
  22. Kubo, K.; Ohyama, S.-I.; Shimizu, T.; Takami, A.; Murooka, H.; Nishitoba, T.; Kato, S.; Yagi, M.; Kobayashi, Y.; Iinuma, N.; Isoe, T.; Nakamura, K.; Iijima, H.; Osawa, T.; Izawa, T. Bioorg. Med. Chem. 2003, 11, 5117. https://doi.org/10.1016/j.bmc.2003.08.020
  23. Pannala, M.; Kher, S.; Wilson, N.; Gaudette, J.; Sircar, I.; Zhang, S.-H.; Bakhirev, A.; Yang, G.; Yuen, P.; Gorcsan, F.; Sakurai, N.; Barbosa, M.; Cheng, J.-F. Bioorg. Med. Chem. Lett. 2007, 17, 5978. https://doi.org/10.1016/j.bmcl.2007.07.071
  24. Wang, Y. D.; Boschelli, D. H.; Johnson, S.; Honores, E. Tetrahedron 2004, 60, 2937. https://doi.org/10.1016/j.tet.2004.02.012
  25. NCI website: www.dtp.nci.nih.gov.
  26. Jin, Y.; Li, H.-Y.; Lin, L.-P.; Tan, J.; Ding, J.; Luo, X.; Long, Y.-Q. Bioorg. Med. Chem. 2005, 13, 5613. https://doi.org/10.1016/j.bmc.2005.05.045
  27. Nautiyal, J.; Yu, Y.; Aboukameel, A.; Kanwar, S. S.; Das, D. J.; Du, J.; Patel, B. B.; Sarkar, F. H.; Rishi, A. K.; Mohammad, R. M.; Majumdar, A. P. N. Mol. Cancer Ther. 2010, 9, 1503. https://doi.org/10.1158/1535-7163.MCT-10-0019
  28. Fasih, A.; Fonge, H.; Cai, Z.; Leyton, J. V.; Tikhomirov, I.; Done, S. J.; Reilly, R. M. Breast Cancer Res. Treat. 2012, 135, 189. https://doi.org/10.1007/s10549-012-2137-y
  29. Lan, K.-H.; Shih, Y.-S.; Chang, C. A.; Yen, S.-H.; Lan, K.-L. Biochem. Biophys. Res. Commun. 2012, 428, 292. https://doi.org/10.1016/j.bbrc.2012.10.050
  30. http://www.dtp.nci.nih.gov/branches/btb/ivclsp.html

Cited by

  1. Hydrogenation of (N,N-disubstituted aminomethyl)nitrobenzenes to (N,N-disubstituted aminomethyl)anilines catalyzed by palladium–nickel bimetallic nanoparticles vol.5, pp.58, 2015, https://doi.org/10.1039/C5RA07208E
  2. ChemInform Abstract: Synthesis and Preliminary Cytotoxicity Evaluation of New Diarylamides and Diarylureas Possessing 2,3‐Dihydropyrrolo[3,2‐b]quinoline Scaffold. vol.44, pp.52, 2013, https://doi.org/10.1002/chin.201352164