Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d] pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 22, 2011, Pages 6808-6817

  Hassan, Ghaneya Sayed ^a   Kadry, Hanan Hassan ^a   Abou Seri, Sahar Mahmoud ^a   Ali, Mamdouh Moawad ^b   Mahmoud, Abeer Essam El Din ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Cytotoxic activity; Oxidative stress; Pyrazole; Pyrazolo 3,4 d pyrimidine

Indexed keywords

1 (4 CHLOROPHENYL) 5 (3,4 DIMETHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYL) 5 (4 HYDROXY 3 METHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYL) 5 (4 METHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYL) 6 METHYL 5 (3,4,5 TRIMETHOXYBENZYLIDENEAMINO) 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYLSULFONYL) 5 (3,4 DIMETHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYLSULFONYL) 5 (3,4,5 TRIMETHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 1 (4 CHLOROPHENYLSULFONYL) 5 (4 METHOXYBENZYLIDENEAMINO) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 5 (BENZYLIDENEAMINO) 1 (4 CHLOROPHENYL) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; 5 (BENZYLIDENEAMINO) 1 (4 CHLOROPHENYLSULFONYL) 6 METHYL 1H PYRAZOLO[3,4 D]PYRIMIDIN 4(5H) ONE; ANTINEOPLASTIC AGENT; CATALASE; CISPLATIN; FREE RADICAL; GLUTATHIONE; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; N [4 (2 BENZYLIDENEHYDRAZINECARBONYL) 1H PYRAZOL 5 YL]ACETAMIDE; N [4 [2 (3,4 DIMETHOXYBENZYLIDENE)HYDRAZINECARBONYL] 1H PYRAZOL 5 YL]ACETAMIDE; N [4 [2 (3,4,5 TRIMETHOXYBENZYLIDENE)HYDRAZINECARBONYL] 1H PYRAZOL 5 YL]ACETAMIDE; N [4 [2 (4 METHOXYBENZYLIDENE)HYDRAZINECARBONYL] 1H PYRAZOL 5 YL]ACETAMIDE; NITRIC OXIDE; NUCLEIC ACID; PYRAZOLEHYDRAZONE DERIVATIVE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BREAST ADENOCARCINOMA; CANCER INHIBITION; CARCINOMA CELL; CELL STRAIN MCF 7; CONFERENCE PAPER; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NUCLEIC ACID SYNTHESIS; PROTEIN SYNTHESIS INHIBITION;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; FEMALE; HUMANS; HYDRAZONES; OXIDATIVE STRESS; PYRAZOLES; PYRIMIDINES; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054978038     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.036     Document Type: Conference Paper

References (61)

1. A. Jemal, R. Siegel, E. Ward, T. Murray, J. Xu, and M.J. Thun CA Cancer J. Clin. 57 2007 43
2. S. Wilhelm, C. Carter, M. Lynch, T. Lowinger, J. Dumas, R.A. Smith, B. Schwartz, R. Simantov, and S. Kelley Nat. Rev. Drug Disc. 5 2006 835
3. S. Rollas, and.G. Küükgüzel Molecules 12 2007 1910
4. Y. Zhao, J. Hui, D. Wang, L. Zhu, J.H. Fang, and X.D. Zhao Chem. Pharm. Bull. 58 2010 1324
5. Y. Xia, C.D. Fan, B.X. Zhao, J. Zhao, D.S. Shin, and J.Y. Miao Eur. J. Med. Chem. 43 2008 2347
6. V. Onnis, M.T. Cocco, R. Fadda, and C. Congiu Bioorg. Med. Chem. 17 2009 6158
7. S. Vogel, D. Kaufmann, M. Pojarová, C. Müller, T. Pfaller, S. Kühne, P.J. Bednarski, and E. Von Angerer Bioorg. Med. Chem. 16 2008 6436
8. A. Andreani, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, G. Lenaz, R. Fato, C. Bergamini, and G. Farruggia J. Med. Chem. 48 2005 3085
9. A. Andreani, S. Burnelli, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, L. Varoli, N. Calonghi, C. Cappadone, G. Farruggia, M. Zini, C. Stefanelli, L. Masotti, N.S. Radin, and R.H. Shoemaker J. Med. Chem. 51 2008 809
10. D.J. Richard, J.C. Verheijen, K. Curran, J. Kaplan, L. Toral-Barza, I. Hollander, J. Lucas, K. Yu, and A. Zask Bioorg. Med. Chem. Lett. 19 2009 6830
11. P. Traxler, G. Bold, J. Frei, M. Lang, N. Lydon, H. Mett, E. Buchdunger, T. Meyer, M. Mueller, and P. Furet J. Med. Chem. 40 1997 3601
12. F. Manetti, A. Santucci, G.A. Locatelli, G. Maga, A. Spreafico, T. Serchi, M. Orlandini, G. Bernardini, N.P. Caradonna, A. Spallarossa, C. Brullo, S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, O. Hoffmann, M. Bologna, A. Angelucci, and M. Botta J. Med. Chem. 50 2007 5579
13. A. Angelucci, S. Schenone, G.L. Gravina, P. Muzi, C. Festuccia, C. Vicentini, M. Botta, and M. Bologna Eur. J. Cancer 42 2006 2838
14. F. Manetti, A. Pucci, M. Magnani, G.A. Locatelli, C. Brullo, A. Naldini, S. Schenone, G. Maga, F. Carraro, and M. Botta Chem. Med. Chem. 2 2007 343
15. S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, L. Mosti, G. Maga, E. Crespan, F. Carraro, F. Manetti, C. Tintori, and M. Botta Eur. J. Med. Chem. 43 2008 2665
16. C.N. Cavasotto, M.A. Ortiz, R.A. Abagyan, and F.J. Piedrafita Bioorg. Med. Chem. Lett. 16 2006 1969
17. F. Carraro, A. Naldini, A. Pucci, G.A. Locatelli, G. Maga, S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, C. Brullo, P. Fossa, G. Menozzi, L. Mosti, M. Modugno, C. Tintori, F. Manetti, and M. Botta J. Med. Chem. 49 2006 1549
18. M.A. Santucci, V. Corradi, M. Mancini, F. Manetti, M. Radi, S. Schenone, and M. Botta Chem. Med. Chem. 4 2009 118
19. M. Radi, E. Dreassi, C. Brullo, E. Crespan, C. Tintori, V. Bernardo, M. Valoti, C. Zamperini, H. Daigl, F. Musumeci, F. Carraro, A. Naldini, I. Filippi, G. Maga, S. Schenone, and M. Botta J. Med. Chem. 54 2011 2610
20. D.C. Kim, Y.R. Lee, B.S. Yang, K.J. Shin, D.J. Kim, B.Y. Chung, and K.H. Yoo Eur. J. Med. Chem. 38 2003 525
21. N. Dessalew, D.S. Patel, and P.V. Bharatam J. Mol. Graph. Model. 25 2007 885
22. J.O. Ban, D.H. Kwak, J.H. Oh, E.J. Park, M.C. Cho, H.S. Song, M.J. Song, S.B. Han, D.C. Moon, K.W. Kang, and J.T. Hong Chem. Biol. Interact. 188 2010 75
23. S. Gupta, L.M. Rodrigues, A.P. Esteves, A.M.F. Oliveira-Campos, M.S.J. Nascimento, N. Nazareth, H. Cidade, M.P. Neves, E. Fernandes, M. Pinto, N.M. Cerqueira, and N. Brás Eur. J. Med. Chem. 43 2008 771
24. A.E. Rashad, A.E. Mahmoud, and M.M. Ali Eur. J. Med. Chem. 46 2011 1019
25. H.H. Kadry, and S. Shouman Az. J. Pharm. Sci. 34 2006 237
26. S. Subramanian, N.S. Kim, P. Thanigaimalai, V.K. Sharma, K.C. Lee, J.S. Kang, H.M. Kim, and S.H. Jung Eur. J. Med. Chem. 46 2011 3258
27. I.M. El-Deeb, S.M. Bayoumi, M.A. El-Sherbeny, and A.A. Abdel-Aziz Eur. J. Med. Chem. 45 2010 2516
28. Hayakawa, M.; Kaizawa, H.; Kawaguchi, K. I.; Matsuda, K.; Ishikawa, N.; Koizumi, T.; Yamano, M.; Okada, M.; Ohta, M. US. Pat. 6403588 B1, 2002.
29. J. Fang, T. Seki, and H. Maeda Adv. Drug Delivery Rev. 61 2009 290
30. B. Demple, and L. Harrison Annu. Rev. Biochem. 63 1994 915
31. K.J. Davies Biochem. Soc. Trans. 21 1993 346
32. T. Lindahl Nature 362 1993 709
33. B.A. Wagner, G.R. Buettner, and C.P. Burns Biochemistry 33 1994 4449
34. H. Pelicano, D. Carney, and P. Huang Drug Resist. Updat. 7 2004 97
35. Y. Hasegawa, T. Takano, A. Miyauchi, F. Matsuzuka, H. Yoshida, K. Kuma, and N. Amino Cancer Lett. 182 2002 69
36. O. Ben-Yoseph, and B.D. Ross Br. J. Cancer 70 1994 1131
37. P. Huang, L. Feng, E.A. Oldham, M.J. Keating, and W. Plunkett Nature 407 2000 390
38. S. Simizu, M. Takada, K. Umezawa, and M. Imoto J. Biol. Chem. 273 1998 26900
39. V.J. Ram, H.N. Pandy, and L. Mishra Arch. Pharm. 312 1979 586
40. C. Alberti, and C. Tironi Farmaco Sci. 22 1967 58
41. P.C. Lima, L.M. Lima, K.C. da-Silva, P.H. Léda, A.L. de-Miranda, C.A. Fraga, and E.J. Barreiro Eur. J. Med. Chem. 35 2000 187
42. A. Kusakiewicz-Dawid, E. Masiukiewicz, B. Rzeszotarska, I. Dybala, A.E. Kozioe, and M.A. Broda Chem. Pharm. Bull. 55 2007 747
43. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107
44. M. Purohit, R.V. Prasad, and C.Y. Mayur Arch. Pharm. 11 2011 248
45. S.M. Abou-Seri Eur. J. Med. Chem. 45 2010 4113
46. B. Brüne Cell Death Differ. 10 2003 864
47. Y. Molina, L. Vedia, B. McDonald, B. Reep, B. Brüne, M. Di Silvio, T.R. Billiar, and E.G. Lapetina J. Biol. Chem. 267 1992 24929
48. J.B. Hibbs Jr., R.R. Taintor, Z. Vavrin, and E.M. Rachlin Biochem. Biophys. Res. Commun. 157 1988 87
49. M.J. Juedes, and G.N. Wogan Mutat. Res. 349 1996 51
50. M. Lepoivre, F. Fieschi, J. Coves, L. Thelander, and M. Fontecave Biochem. Biophys. Res. Commun. 179 1991 442
51. K. Fehsel, A. Jalowy, S. Qi, V. Burkart, B. Hartmann, and H. Kolb Diabetes 42 1993 496
52. P. Bienvenu, L. Caron, D. Gasparutto, and J.F. Kergonou EXS. 62 1992 257
53. D.A. Gewirtz Biochem. Pharmacol. 57 1999 727
54. D.E. Paglia, and W.N. Valentine J. Lab. Clin. Med. 70 1967 158
55. H. Aebi Method of Enzymatic Analysis Vol. 2 1984 Academic Press New York pp 673-679
56. S. Marklund, and G. Marklund Eur. J. Biochem. 47 1974 469
57. S.P. Wolff Methods Enzymol. 233 1994 182
58. H.A.C. Montgomery, and J.F. Dymock Analyst 86 1961 414
59. G.L. Ellman Arch. Biochem. Biophys. 82 1959 70
60. T. Zhou, G. Zhou, W. Song, N. Eguchi, W. Lu, E. Lundin, T. Jin, and G. Nordberg Toxicology 142 1999 1
61. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265