Curcumin-I Knoevenagel's condensates and their Schiff's bases as anticancer agents: Synthesis, pharmacological and simulation studies

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 13, 2013, Pages 3808-3820

  Ali, Imran ^a   Haque, Ashanul ^a   Saleem, Kishwar ^a   Hsieh, Ming Fa ^b  

^a JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

^b CHUNG YUAN CHRISTIAN UNIVERSITY   (Taiwan)

Author keywords

Anticancer agents; Curcumin I derivatives; DNA binding and hemolysis and cell line profiles; Docking studies

Indexed keywords

1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [[3 (2 HYDROXYPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLIDENE]HEPTA 1,6 DIENE 3,5 DIONE; 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [[3 (3 NITROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLIDENE]HEPTA 1,6 DIENE 3,5 DIONE; 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [[3 (4 NITROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLIDENE]HEPTA 1,6 DIENE 3,5 DIONE; 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [[3 (4CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 4 YL]METHYLIDENE]HEPTA 1,6 DIENE 3,5 DIONE; 3 (2 HYDROXYPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOLE 4 CARBALDEHYDE; 3 (3 NITROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOLE 4 CARBALDEHYDE; 3 (4 CHLOROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOLE 4 CARBALDEHYDE; 3 (4 NITROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOLE 4 CARBALDEHYDE; 5 [(CARBAMOYLAMINO)IMINO] 1,5 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [1 [3 (2 HYDROXYPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 4 YLIDENE]ETHYL]HEPTA 1,6 DIEN 3 YLIDEN AMIN UREA; 5 [(CARBAMOYLAMINO)IMINO] 1,5 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [1 [3 (3 NITROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 4 YLIDENE]ETHYL]HEPTA 1,6 DIEN 3 YLIDEN AMIN UREA; 5 [(CARBAMOYLAMINO)IMINO] 1,5 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [1 [3 (4 CHLOROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 4 YLIDENE]ETHYL]HEPTA 1,6 DIEN 3 YLIDEN AMIN UREA; 5 [(CARBAMOYLAMINO)IMINO] 1,5 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 [1 [3 (4 NITROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 4 YLIDENE]ETHYL]HEPTA 1,6 DIEN 3 YLIDEN AMIN UREA; ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; SCHIFF BASE; UNCLASSIFIED DRUG; CURCUMIN; DNA; PYRAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA ADDUCT; DRUG DNA BINDING; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; KNOEVENAGEL CONDENSATION; MOLECULAR DOCKING; ANALOGS AND DERIVATIVES; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HEMOLYSIS; MCF 7 CELL LINE; METABOLISM; NEOPLASMS; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CURCUMIN; DNA; HEMOLYSIS; HUMANS; MCF-7 CELLS; MOLECULAR DOCKING SIMULATION; NEOPLASMS; PYRAZOLES; SCHIFF BASES;

EID: 84878585945     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.04.018     Document Type: Article

References (54)

1. World Health Statistics 2012. World Health Organization: Geneva, 2012.
2. American Cancer Society Cancer Facts & Figures 2012 2012 American Cancer Society Atlanta
3. R. Dikshit, P.C. Gupta, C. Ramasundarahettige, V. Gajalakshmi, L. Aleksandrowicz, R. Badwe, R. Kumar, S. Roy, W. Suraweera, F. Bray, M. Mallath, P.K. Singh, D.N. Sinha, A.S. Shet, H. Gelband, and P. Jha Lancet 2012 1807 379
4. S. Isakoff Cancer J. 16 2010 53
5. D.J. Newman, and G.M.J. Cragg Nat. Prod. 75 2012 311
6. N.I. Vasilevich, R.V. Kombarov, D.V. Genis, and M.A. Kirpichenok J. Med. Chem. 55 2012 7003
7. I. Ali, Saleem K. Rahisuddin, A. Haque, and A. El-Azzouny Egypt. Pharm. J. 9 2010 133
8. K.H. Lee, F.H. Ab Aziz, A. Syahida, F. Abas, K. Shaari, D.A. Israf, and N.H. Lajis Eur. J. Med. Chem. 44 2009 3195
9. P. Venkatesan, and M.N. Rao J. Pharm. Pharmacol. 52 2000 1123
10. B.B. Aggarwal, A. Kumar, and A.C. Bharti Anticancer Res. 23 2003 363
11. M.W. Amolins, L.B. Peterson, and B.S. Blagg Bioorg. Med. Chem. 17 2009 360
12. S. Padhye, D. Chavan, S. Pandey, J. Deshpande, K.V. Swamy, and F.H. Sarkar Mini-Rev. Med. Chem. 10 2010 372
13. P.K. Sahu, P.K. Sahu, S.K. Gupta, D. Thavaselvam, and D.D. Agarwal Eur. J. Med. Chem. 54 2012 366
14. S. Mishra, K. Karmodiya, N. Surolia, and A. Surolia Bioorg. Med. Chem. 16 2008 2894
15. X. Qiu, Y. Du, B. Lou, Y. Zuo, W. Shao, Y. Huo, J. Huang, Y. Yu, B. Zhou, J. Du, H. Fu, and X. Bu J. Med. Chem. 53 2010 8260
16. D. Simoni, M. Rizzi, R. Rondanin, R. Baruchello, P. Marchetti, F.P. Invidiata, M. Labbozzetta, P. Poma, V. Carina, M. Notarbartolo, A. Alaimo, and N.D. Alessandro Bioorg. Med. Chem. Lett. 18 2008 845
17. I. Ali, K. Saleem, D. Wesselinova, and A. Haque Med. Chem. Res. 22 2013 1386
18. S. Howard, V. Berdini, J.A. Boulstridge, M.G. Carr, D.M. Cross, J. Curry, L.A. Devine, T.R. Early, L. Fazal, A.L. Gill, M. Heathcote, S. Maman, J.A. Matthews, R.L. McMenamin, E.F. Navarro, M.A. O'Brien, M. O'Reilly, D.C. Rees, M. Reule, D. Tisi, G. Williams, M. Vinkovic, and P.G. Wyatt J. Med. Chem. 52 2009 379
19. A.A. Bekhit, and T. Abdel-Aziem Bioorg. Med. Chem. 12 2004 1935
20. A. Adhikari, B. Kalluraya, K.V. Sujith, K. Gouthamchandra, R. Jairam, and R. Mahmood Eur. J. Med. Chem. 55 2012 467
21. G.M. Nitulescu, C. Draghici, and A.V. Missir Eur. J. Med. Chem. 45 2010 4914
22. I. Bouabdallah, L. M'Barek, A. Zyad, A.A. Ramdani, I. Zidane, and A. Melhaoui Nat. Prod. Res. 21 2007 298
23. D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, L. Zaprutko, A. Gzella, and R. Lesyk Eur. J. Med. Chem. 44 2009 1396
24. M. Shaharyar, M.M. Abdullah, M.A. Bakht, and J. Majeed Eur. J. Med. Chem. 45 2010 114
25. H. Situ, and L. Bobek Antimicrob. Agents Chemother. 44 2000 1485
26. M.S. Christie, L.R. Kenneth, and B.W. David Toxicol. Sci. 97 2007 163
27. J.K. Barton, A. Danishefsky, and J. Goldberg J. Am. Chem. Soc. 106 1984 2172
28. N. Shahabadi, S. Kashanian, and M. Purfoulad Spectrochim. Acta, Part A 72 2009 757
29. X.W. Liu, J. Li, H. Deng, K.C. Zheng, Z.W. Mao, and L.N. Ji Inorg. Chim. Acta 358 2005 3311
30. X.W. Liu, J. Li, H. Li, K.C. Zheng, H. Chao, and L.N. Ji J. Inorg. Biochem. 99 2005 2372
31. J.G. Liu, Q.L. Zhang, X.F. Shi, and L.N. Ji Inorg. Chem. 40 2001 5045
32. A.M. Pyle, J.P. Rehmann, R. Meshoyrer, C.V. Kumar, N.J. Turro, and J.K. Barton J. Am. Chem. Soc. 111 1989 3051
33. R. Indumathy, M. Kanthimathi, T. Weyhermuller, and B.U. Nair Polyhedron 27 2008 3443
34. C.S. Allardyce, P.J. Dyson, D.J. Ellis, and S.L. Heath Chem. Commun. 2001 1396
35. R.F. Pasternack, E.J. Gibbs, and J. Villafrancas J. Biochem. 22 1983 2406
36. P. Zhao, L. Xu, J. Huang, J. Liu, H. Yu, K. Zheng, and L. Ji Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 71 2008 1216
37. H. Guo, C. Cai, H. Gong, and X. Chen Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc. 79 2011 92
38. G. Psomas, A. Tarushi, and E.K. Efthimiadou Polyhedron 27 2008 133
39. L.M. Chen, J. Liu, J.C. Chen, C.P. Tan, S. Shi, K.C. Zheng, and L.N. Ji J. Inorg. Biochem. 102 2008 330
40. G. Pratviel, J. Bernadou, and B. Meunier Adv. Inorg. Chem. 45 1998 251
41. F. Arjmand, S. Parveen, M. Afzal, L. Toupet, and T. Ben Hadda Eur. J. Med. Chem. 49 2012 141
42. I. Haq Arch. Biochem. Biophys. 403 2002 1
43. Y. Sun, H. Zhang, S. Bi, X. Zhouf, L. Wang, and Y. Yan J. Lumin. 131 2011 2299
44. S.M. Bayomi, H.A. El-Kashef, M.B. El-Ashmawy, M.N.A. Nasr, M.A. El-Sherbeny, F.A. Badria, L.A. Abou-zeid, M.A. Ghaly, and N.I. Abdel-Aziz Med. Chem. Res. 22 2013 1147
45. S. Neidle Nat. Prod. Rep. 18 2001 291
46. P.L. Hamilton, and D.P. Arya Nat. Prod. Rep. 29 2012 134
47. L. Péret-Almeida, A.P.F. Cherubino, R.J. Alves, L. Dufossé, and M.B.A. Gloria Food Res. Int. 38 2005 1039
48. ASTM F756-00 Standard Practice for Assessment of Hemolytic Properties of Materials 2000 ASTM International West Conshohocken, PA, USA 10.1520/F0756-00
49. A. Wolfe, G.H. Shimer Jr., and T. Meehan Biochemistry 26 1987 6392
50. T. Mosman J. Immunol. Methods 65 1983 55
51. M.F. Sanner J. Mol. Graph Model 17 1999 57
52. G.M. Morris, G.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
53. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605
54. R.A. Laskowski, and M.B. Swindells J. Chem. Inf. Model. 51 2011 2778