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

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Synthesis, Crystal Structure, Spectral Characterization and Cytotoxic Activity of Novel Ethyl 2-Cyano-3-(quinolin-3-ylamino)acrylate

https://doi.org/10.14233/ajchem.2014.17077
M.M. Ghorab
Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia; Deprtment of Drug Radiation Research, National Center for Radiation Research and Technology, Atomic Energy Authority, P.O. Box 29, Nasr City, Cairo, Egypt
M.S. Alsaid
Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia
H.A. Ghabbour
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
H.-K. Fun
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia ;Chemistry of Natural Products Group, Center of Excellence for Advanced Sciences, National Research Center, Dokki, 12622, Cairo, Egypt

Corresponding Author(s) : M.M. Ghorab

mmsghorab@yahoo.com

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

Abstract

The chemistry of quinoline derivatives has been of increasing interest, since many of these compounds exhibited several biological activities and useful application as antitumor. On the account of the reported anticancer activity of quinolines containing the different biologically active moieties, a novel ethyl 2-cyano-3-(quinolin-3-ylamino)acrylate (2) was synthesized using 3-aminoquinoline (1) as strategic starting material. Interaction of 3-aminoquinoline (1) with ethyl 2-cyano-3-ethoxyacrylate furnished the corresponding ethyl-2-cyano-3-(quinolin-3-ylamino)acrylate (2). The structure of th newly synthesized compound was confirmed by elemental analysis, IR, 1H NMR, 13C NMR spectra and X-ray analysis. The target compound was subjected to in vitro cytotoxic activity against ehrlich ascites carcinoma cells. This compound showed higher activity with IC50 (25 μg/mL) when compared with doxorubicin [CAS 23214-92-8] as a reference drug (IC50 value 37.5 μg/mL).

Keywords

Novel quinoline X-ray crystallographic study and cytotoxic activity
Ghorab, M., Alsaid, M., Ghabbour, H., & Fun, H.-K. (2014). Synthesis, Crystal Structure, Spectral Characterization and Cytotoxic Activity of Novel Ethyl 2-Cyano-3-(quinolin-3-ylamino)acrylate. Asian Journal of Chemistry, 26(21), 7393–7396. https://doi.org/10.14233/ajchem.2014.17077
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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 and J.B. Milbank, 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 and 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, 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, 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, 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, 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, S. A. Aboulmagd, Eur. J. Med. Chem, 45, 171 (2010); doi:10.1016/j.ejmech.2009.09.039.
  36. Brucker. APEX2, SAINT and SADABS. Brucker 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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