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

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Synthesis, Crystal Structure and Anti-Breast Cancer Activity of Some Enaminone Derivatives

https://doi.org/10.14233/ajchem.2014.17171
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, Kingdom of Saudi Arabia
Hoong-Kun Fun
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of 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

The present work reports the synthesis of some enaminone derivatives bearing a biologically active 3,4-dimethoxyphenyl (3) or 3,4,5-trimethoxyphenyl moieties (5 and 7), respectively. The trimethoxybenzene moiety has been previously reported to confer cytotoxic activity. The structure of the newly synthesized compounds was verified by elemental analyses, IR, 1H NMR, 13C NMR spectra and X-ray analysis. The anti-breast cancer activity of the enaminone derivatives were evaluated. Compounds 3, 5 and 7 showed excellent anti-breast cancer activity with IC50 values (55.2, 79.06 and 50.49 μM) compared with doxorubicin with IC50 value (71.80 μM) as reference drug.

Keywords

Synthesis Enaminones X-ray analysis Anti-breast cancer activity
M. Ghorab, M., S. Alsaid, M., A. Ghabour, H., & Fun, H.-K. (2014). Synthesis, Crystal Structure and Anti-Breast Cancer Activity of Some Enaminone Derivatives. Asian Journal of Chemistry, 26(21), 7424–7430. https://doi.org/10.14233/ajchem.2014.17171
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References
  1. A.G. Cook, In: Enaminas: Synthesis, Structure and Reaction, Marcel Dekker; New York, NY, USA (1969).
  2. A.D. Fraser, Clin. Biochem., 29, 97 (1996); doi:10.1016/0009-9120(95)02027-6.
  3. R.J. Porter, J.J. Cereghino, G.D. Gladding, B. Hessie, H.J. Kupferberg, B. Scoville and B.G. White, Clin. Q, 51, 293 (1984); doi:10.3949/ccjm.51.2.293.
  4. D.S. Cox and H. Gao, Eur. J. Pharm. Biopharm., 52, 145 (2001); doi:10.1016/S0939-6411(01)00172-2.
  5. D.S. Cox, K.R. Scott, H. Gao, S. Raje and N.D. Eddington, J. Pharm. Sci., 90, 1540 (2001); doi:10.1002/jps.1104.
  6. J. Vamecq, D. Lambert, J.H. Poupaert, B. Masereel and J.P. Stables, Eur. J. Med. Chem., 38, 49 (2003); doi:10.1016/S0223-5234(02)00006-5.
  7. N.D. Eddington, D.S. Cox, M. Khurana, N.N. Salama, J.P. Stables, S.J. Harrison, A. Negussie, R. Taylor, U.Q. Tran, J.A. Moore, J.C. Barrow and K.R Scott, Eur. J. Med. Chem., 38, 49 (2003); doi:10.1016/S0223-5234(02)00006-5.
  8. N.D. Eddington, D.S. Cox, R.R. Roberts, R.J. Butcher, I.O. Edafiogho, J.P. Stables, N. Cooke, A.M. Goodwin, C.A. Smith and K.R. Scott, Eur. J. Med. Chem., 37, 635 (2002); doi:10.1016/S0223-5234(02)01377-6.
  9. I.O. Edafiogho, K.V. Ananthalakshmi and S.B. Kombian, Bioorg. Med. Chem., 14, 5266 (2006); doi:10.1016/j.bmc.2006.03.049.
  10. K.V. Ananthalakshmi, I.O. Edafiogho and S.B. Kombian, Neuroscience, 141, 345 (2006); doi:10.1016/j.neuroscience.2006.03.021.
  11. C.L. Arthurs, G.A. Morris, M. Piacenti, R.G. Pritchard, I.J. Stratford, T. Tatic, R.C. Whitehead, K.F. Williams and N.S. Wind, Tetrahedron, 66, 9049 (2010); doi:10.1016/j.tet.2010.08.072.
  12. M. Kandhavelu, L. Paturu, A. Mizar, K. Mahmudov, M. Kopylovich, M. Karp, O. Yli-Harja, A. Pombeiro and A. Ribeiro, Pharm. Chem. J., 46, 157 (2012); doi:10.1007/s11094-012-0751-y.
  13. S.M. Alsaid, M.S. Bashandy and M.M. Ghorab, Arzneimittelfoorschung, 61, 527 (2011); doi:10.1055/s-0031-1296239.
  14. S.I. Alqasoumi, A.M. Al-Taweel, A.M. Alafeefy, M.M. Hamed, E. Noaman and M.M. Ghorab, Bioorg. Med. Chem. Lett., 19, 6939 (2009); doi:10.1016/j.bmcl.2009.10.065.
  15. M.M. Ghorab, F.A. Ragab, E. Noaman, H.I. Heiba and E.M. El-Hossary, Arzneimittelforschung, 58, 35 (2008); doi:10.1055/s-0031-1296464.
  16. M.M. Ghorab, F.A. Ragab, E. Noaman, H.I. Heiba and E.M. El-Hossary, Arzneimittelforschung, 57, 795 (2007); doi:10.1055/s-0031-1296682.
  17. M.M. Ghorab, F.A. Ragab and M.M. Hamed, Eur. J. Med. Chem., 44, 4211 (2009); doi:10.1016/j.ejmech.2009.05.017.
  18. 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.
  19. M.M. Ghorab, M.S. Alsaid and E.M. El-Hossary, J. Heterocycl. Chem., 48, 563 (2011); doi:10.1002/jhet.619.
  20. M.M. Ghorab, F.A. Ragab and M.M. Hamed, Arzneimittelforschung, 60, 141 (2010); doi:10.1055/s-0031-1296263.
  21. V. V. Kouznetsov, F. A. Rojas Ruiz, L. Y. Vargas Mendez and M. P. Gupta, Lett. Drug Des. Discov., 9, 680 (2012); doi:10.2174/157018012801319544.
  22. S. Eswaran, A.V. Adhikari, I.H. Chowdhury, N.K. Pal and K.D. Thomas, Eur. J. Med. Chem., 45, 3374 (2010); doi:10.1016/j.ejmech.2010.04.022.
  23. E.W. Chia, A.N. Pearce, M.V. Berridge, L. Larsen, N.B. Perry, C.E. Sansom, C.A. Godfrey, L.R. Hanton, G.L. Lu, M. Walton, W.A. Denny, V.L. Webb, B.R. Copp and J.L. Harper, Bioorg. Med. Chem., 16, 9432 (2008); doi:10.1016/j.bmc.2008.09.052.
  24. M.M.F. 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.
  25. 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.
  26. M. Sankaran, C. Kumarasamy, U. Chokkalingam and P.S. Mohan, Bioorg. Med. Chem. Lett., 20, 7147 (2010); doi:10.1016/j.bmcl.2010.09.018.
  27. S.M. Abdel- Gawad, M.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.
  28. M.M. Ghorab, M.S. Alsaid and Y.M. Nissan, Chem. Pharm. Bull. (Tokyo), 60, 1019 (2012); doi:10.1248/cpb.c12-00292.
  29. M.S. Alsaid, M.M. Ghorab and Y.M. Nissan, Chem. Cent. J., 6, 64 (2012); doi:10.1186/1752-153X-6-64.
  30. M.M. Ghorab, M.S. Alsaid and Y.M. Nissan, Arzneimittelforschung, 62, 497 (2012); doi:10.1055/s-0032-1323660.
  31. M.M. Ghorab and M.S. Alsaid, Arch. Pharm. Res., 35, 965 (2012); doi:10.1007/s12272-012-0603-z.
  32. M.M. Ghorab and M.S. Alsaid, Arch. Pharm. Res., 35, 987 (2012); doi:10.1007/s12272-012-0605-x.
  33. E.M. Kassem, E.R. El-Sawy, H.I. Abd-Alla, A.H. Mandour, D. Abdel-Mogeed and M.M. El-Safty, Arch. Pharm. Res., 35, 955 (2012); doi:10.1007/s12272-012-0602-0.
  34. Bruker, APEX2, SAINT & SADABS. Bruker AXS Inc., Madison, Wisconsin, USA (2009).
  35. G.M. Sheldrick, Acta Crystallogr., A64, 112 (2008); doi:10.1107/S0108767307043930.
  36. A.L. Spek, Acta Crystallogr., D65, 148 (2009); doi:10.1107/S090744490804362X.
  37. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975); doi:10.1021/ja00839a011.
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