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Vol. 26 No. 21 (2014): Vol 26 Issue 21

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Synthesis, Crystal Structure and Antitumor Activity of Novel 2-Cyano-N-(quinolin-3-yl)acetamide

https://doi.org/10.14233/ajchem.2014.17050
Mostafa M. Ghorab
Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia
Mansour S. Alsaid
Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia
Hazem A. Ghabour
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Hoong-Kun Fun
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia

Corresponding Author(s) : Mostafa M. Ghorab

mmsghorab@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21

Abstract

Cancer has been ranked second after cardiovascular diseases. The plant-derived molecules have played an important role for the treatment of cancer. On the account of the reported anticancer activity of quinoline containing biologically active cyanoacetamide moiety, a novel 2-cyano-N-(quinolin-3-yl)acetamide (2) was synthesized using 3-aminoquinoline (1) as strategic starting materials. The corresponding 2-cyano-N-(quinoline-3-yl)-acetamide (2) was obtained in good yield via reaction of 3-aminoquinoline (1) with ethylcyanoacetate in dry toluene. The structure of the newly synthesized compound was confirmed on the basis of elemental analyses, IR, 1H NMR, 13C NMR spectra and X-ray analysis. Compound 2 was found to exert the most powerful effect on Ehrlich ascites carcinoma tumor cells (in vitro) compared with the positive control (doxorubicin) with IC50 of 2.14 μg/mL.

Keywords

Novel quinoline derivative X-ray crystallography Antitumor activity
M. Ghorab, M., S. Alsaid, M., A. Ghabour, H., & Fun, H.-K. (2014). Synthesis, Crystal Structure and Antitumor Activity of Novel 2-Cyano-N-(quinolin-3-yl)acetamide. Asian Journal of Chemistry, 26(21), 7389–7392. https://doi.org/10.14233/ajchem.2014.17050
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References
  1. P. Nasveld and S. Kitchener, Trans. R. Soc. Trop. Med. Hyg., 99, 2 (2005); doi:10.1016/j.trstmh.2004.01.013.
  2. P.A. Leatham, H. A. Bird, V. Wright, D. Seymour and A. Gordon, Eur. J. Rheumatol. Inflamm., 6, 209 (1983).
  3. W.A. Denny, W.R. Wilson, D.C. Ware, G.J. Atwell, J.B. Milbank and R.J. Stevenson, US Patent 7064117 (2006).
  4. N. Muruganantham, R. Sivakumar, N. Anbalagan, V. Gunasekaran and J.T. Leonard, Biol. Pharm. Bull., 27, 1683 (2004); doi:10.1248/bpb.27.1683.
  5. M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); doi:10.1021/jm00040a003.
  6. W.D. Wilson, M. Zhao, S.E. Patterson, R.L. Wydra, L. Janda, L. Strekowski, Med. Chem. Res., 2, 102 (1992).
  7. L. Strekowski, J.L. Mokrosz, V.A. Honkan, A. Czarny, M.T. Cegla, R.L. Wydra, S.E. Patterson and R.F. Schinazi, J. Med. Chem., 34, 1739 (1991); doi:10.1021/jm00109a031.
  8. M. Gopal, S. Shenoy and L.S. Doddamani, J. Photochem. Photobiol. B, 72, 69 (2003); doi:10.1016/j.jphotobiol.2003.09.003.
  9. Y.H. Kim, K.J. Shin, T.G. Lee, E. Kim, M.S. Lee, S.H. Ryu and P.G. Suh, Biochem. Pharmacol., 69, 1333 (2005); doi:10.1016/j.bcp.2004.12.019.
  10. Y.L. Zhao, Y.L. Chen, F.S. Chang and C.C. Tzeng, Eur. J. Med. Chem., 40, 792 (2005); doi:10.1016/j.ejmech.2005.03.008.
  11. L.H. Hurley, Nat. Rev. Cancer, 2, 188 (2002); doi:10.1038/nrc749.
  12. M. Israel, L.C. Jones and E.J. Modest, J. Heterocycl. Chem., 9, 255 (1972); doi:10.1002/jhet.5570090213.
  13. B. Vigante, G. Tirzitis, D. Tirzite, B. Chekavichus, J. Uldrikis, A. Sobolev and G. Duburs, Chem. Heterocycl. Compd., 43, 225 (2007); doi:10.1007/s10593-007-0035-8.
  14. T. Utsugi, K. Aoyagi, T. Asao, S. Okazaki, Y. Aoyagi, M. Sano, K. Wierzba and Y. Yamada, Jpn. J. Cancer Res., 88, 992 (1997); doi:10.1111/j.1349-7006.1997.tb00320.x.
  15. M. Manpadi, P.Y. Uglinskii, S.K. Rastogi, K.M. Cotter, Y.-S.C. Wong, L.A. Anderson, A.J. Ortega, S. Van slambrouck, W.F.A. Steelant, S. Rogelj, P. Tongwa, M.Y. Antipin, I.V. Magedov and A. Kornienko, Org. Biomol. Chem., 5, 3865 (2007); doi:10.1039/b713820b.
  16. R. Ghahremanzadeh, G. Imani Shakibaei, S. Ahadi and A. Bazgir, J. Comb. Chem., 12, 191 (2010); doi:10.1021/cc900130a.
  17. F. Abbate, A. Casini, T. Owa, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 14, 217 (2004); doi:10.1016/j.bmcl.2003.09.062.
  18. M. M. Ghorab, E. Noaman, M. M. Ismail, H. I. Heiba, Y. A. Ammar and M. Y. Sayed, Arzneimittelforschung, 56, 405 (2006); doi:10.1055/s-0031-1296742.
  19. M. M. Ismail, M. M. Ghorab, E. Noaman, Y. A. Ammar, H. I. Heiba and M. Y. Sayed, Arzneimittelforschung, 56, 301 (2006); doi:10.1055/s-0031-1296725.
  20. S.A. Rostom, Bioorg. Med. Chem., 14, 6475 (2006); doi:10.1016/j.bmc.2006.06.020.
  21. C.T. Supuran, A. Casini, A. Mastrolorenzo and A. Scozzafava, Mini Rev. Med. Chem., 4, 625 (2004); doi:10.2174/1389557043403792.
  22. C.T. Supuran and A. Scozzafava, Exp. Opin. Ther. Patents, 10, 575 (2000); doi:10.1517/13543776.10.5.575.
  23. T.H. Maren, Annu. Rev. Pharmacol. Toxicol., 16, 309 (1976); doi:10.1146/annurev.pa.16.040176.001521.
  24. C.T. Supuran and A. Scozzafava, Curr. Med. Chem. Immunol. Endocr. Metab. Agents, 1, 61 (2001); doi:10.2174/1568013013359131.
  25. A. J. Kivela, J. Kivela, J. Saamio and S. Parkkila, World J. Gastroenterol., 11, 155 (2005).
  26. W.R. Chegwidden, S.J. Dodgson and I.M. Spencer, EXS, 90, 343 (2000).
  27. M.M. Ghorab, M.S. Alsaid and Y.M. Nissan, Chem. Pharm. Bull (Tokyo), 60, 1019 (2012); doi:10.1248/cpb.c12-00292.
  28. M.S. Alsaid, M.M. Ghorab and Y.M. Nissan, Chem. Cent. J., 6, 64 (2012); doi:10.1186/1752-153X-6-64.
  29. M.M. Ghorab, M.S. Alsaid and Y.M. Nissan, Arzneimittelforschung, 62, 497 (2012); doi:10.1055/s-0032-1323660.
  30. M.M. Ghorab and M.S. Alsaid, Arch. Pharm. Res., 35, 965 (2012); doi:10.1007/s12272-012-0603-z.
  31. M.M. Ghorab and M.S. Alsaid, Arch. Pharm. Res., 35, 987 (2012); doi:10.1007/s12272-012-0605-x.
  32. S. M. Abdel-Gawad, M. S. A. El-Gaby, H. I. Heiba, H. M. Aly and M. M. Ghorab, J. Chin. Chem. Soc., 52, 1227 (2005); doi:10.1002/jccs.200500177.
  33. M.M. Ghorab, M.S. Alsaid and E.M. El-Hossary, J. Heterocycl. Chem., 48, 563 (2011); doi:10.1002/jhet.619.
  34. S.I. Alqasoumi, A.M. Al-Taweel, A.M. Alafeefy, E. Noaman and M.M. Ghorab, Eur. J. Med. Chem., 45, 738 (2010); doi:10.1016/j.ejmech.2009.11.021.
  35. M.M. Ghorab, F.A. Ragab, S.I. Alqasoumi, A.M. Alafeefy and S.A. Aboulmagd, Eur. J. Med. Chem., 45, 171 (2010); doi:10.1016/j.ejmech.2009.09.039.
  36. Bruker, APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA ( 2009).
  37. G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
  38. M. El-Merzabani, A. El-Aaser, A. El-Duweini and A. El-Masry, Planta Med., 36, 87 (1979); doi:10.1055/s-0028-1097246.
  39. D. Raffa, G. Daidone, B. Maggio, S. Cascioferro, F. Plescia and D. Schillaci, IL Farmaco, 59, 215 (2004); doi:10.1016/j.farmac.2003.10.004.
  40. D.J. Takemoto, C. Dunford and M.M. McMurray, Toxicon, 20, 593 (1982); doi:10.1016/0041-0101(82)90053-8.
  41. M. El-Merzabani, A. El-Aaser, M. Attia, A. El-Duweini and A. Ghazal, Planta Med., 36, 150 (1979); doi:10.1055/s-0028-1097255.
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