Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells

European Journal of Medicinal Chemistry

Volumn 46, Issue 4, 2011, Pages 1019-1026

  Rashad, Aymn E ^a   Mahmoud, Abeer E ^a   Ali, Mamdouh M ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

MCF 7; Nucleosides; Pyrazolo 3,4 d pyrimidines; Reactive oxygen species; S Alkyl derivatives

Indexed keywords

(4 ETHYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE 4(3H) THIONE; 4 (1 BETA DEXTRO RIBOFURANOSYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2 ETHOXYCARBONYMETHYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2 ETHOXYETHYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2 METHOXYETHYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (2',3',5' TRI O BENZOYL BETA DEXTRO RIBOFURANOSYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 (BETA DEXTRO GLUCOPYRANOSYLSULFANYL) 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; 4 CHLORO 1 (9 METHYL 5,6 DIHYDRONAPHTHO[1',2':4,5]THIENO[2,3 D]PYRIMIDIN 11 YL) 1H PYRAZOLO[3,4 D]PYRIMIDINE; CATALASE; CISPLATIN; GLUTATHIONE; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN MCF 7; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; OXIDATIVE STRESS;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; PYRAZOLES; PYRIMIDINES; REACTIVE OXYGEN SPECIES; THIONUCLEOSIDES;

EID: 79952280305     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.013     Document Type: Article

References (44)

1. A.E. Rashad, H.H. Sayed, A.H. Shamroukh, and H.M. Awad Phosphorus Sulfur Silicon Relat. Elem. 180 2005 2767 2777
2. A.E. Rashad, A.H. Shamroukh, M.I. Hegab, and H.M. Awad Acta Chim. Slov 52 2005 429 434
3. A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, J.A. Micky, and F.M.E. Abdel-Megeid Bioorg. Med. Chem. 16 2008 7102 7106
4. A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, N.A. Fatahala, and F.M.E. Abdel-Megeid Eur. J. Med. Chem. 44 2009 3285 3292
5. C.N. Khobragade, R.G. Bodade, S.G. Konda, B.S. Dawane, and A.V. Manwar Eur. J. Med. Chem. 45 2010 1635 1638
6. D. Raffa, B. Maggio, F. Plescia, S. Cascioferro, M.V. Raimondi, S. Plescia, and M.G. Cusimano M. Arch. Pharm. 342 2009 321 326
7. 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 771 780
8. S. Schenone, O. Bruno, F. Bondavalli, A. Ranise, L. Mosti, G. Menozzi, P. Fossa, S. Donnini, A. Santoro, M. Ziche, F. Manetti, and M. Botta Eur. J. Med. Chem. 39 2004 939 946
9. M.M. Ghorab, F.A. Ragab, S.I. Alqasoumi, A.M. Alafeefy, and S.A. Aboulmagd Eur. J. Med. Chem. 45 2010 171 178
10. M.M. El-Enany, M.M. Kamel, O.M. Khalil, and H.B. El-Nassan Eur. J. Med. Chem. 45 2010 5286 5291
11. A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, M.M. Ali, and F.M.E. Abdel-Megeid Phosphorus Sulfur Silicon Relat. Elem. 185 2010 74 83
12. B.M. Pfeiffer, G. Atassi, J. Hickman, and A. Pierré Clin. Cancer Res. 7 2001 2573 2580
13. M. Sundaresan, Z.X. Yu, V.J. Ferrans, K. Irani, and T. Finkel Science 270 2001 296 299
14. D. Bernard, K. Gosselin, D. Monte, C. Vercamer, F. Bouali, and A. Pourtier Cancer Res. 64 2004 472 481
15. P.M. Hwang, F. Bunz, J. Yu, C. Rago, T.A. Chan, and M.P. Murphy Nat. Med. 7 2001 1111 1117
16. A. Laurent, C. Nicco, C. Chéreau, C. Goulvestre, J. Alexandre, and A. Alves Cancer Res. 65 2005 948 956
17. S.P. Hussain, P. Amstad, P. He, A. Robles, S. Lupold, and I. Kaneko Cancer Res. 64 2004 2350 2356
18. H. Pelicano, D. Carney, and P. Huang Drug Resist. Updat 7 2004 97 110
19. J. Alexandre, C. Nicco, C. Chéreau, A. Laurent, B. Weill, F. Goldwasser, and F. Batteux J. Natl. Cancer Inst. 98 2006 236 244
20. A.K. Das A Text Book on Medicinal Aspects of Bio-Inorganic Chemistry 1990 CBS India pp. 70-90
21. A.E. Rashad, M.M. Mohamed, M.E.A. Zaki, and S.S. Fatahala Arch. Pharm. 339 2006 664 669
22. M.M. Mohamed, A.E. Rashad, M. Abdel-Moneim, S.S. Fatahala, Z. Naturforsch. C 62c, (2007) 27-31.
23. N.A. Hassan, M.I. Hegab, A.E. Rashad, A.A. Fahmy, and F.M.E. Abdel-Megeid Nucleosides, Nucleotides 26 2007 379 390
24. W.A. Shendy, A.E. Rashad, S.M. Awad, and M.M. Ali Nucleosides, Nucleotides 28 2009 261 274
25. A.E. Rashad, A.H. Shamroukh, R.E. Abdel-Megeid, A. Moustafa, M.A. Ali, and K. Banert Nucleosides, Nucleotides 29 2010 809 820
26. U. Niedballa, and H. Vorbrüggen J. Org. Chem. 39 1974 3654 3660
27. C.K. Pillai, and K.S. Pillai Ind. J. Physiol. Pharmacol. 46 2002 1 5
28. J.W. Tracy, and L.T. Webster Drug used in chemotherapy of protozoal infection: malaria J.G. Hardman, L.E. Limbird, A.G. Gilman, Goodman & Gilman's the Pharmacological Basis of Therapeutics tenth ed. 2001 Mcgraw Hill New York 1069 1079
29. H.L. Huang, L.W. Fang, S.P. Lu, C.K. Chou, T.Y. Luh, and M.Z. Lai Oncogene 22 2003 168 8177
30. M. Düchler, M. Staczyk, M. Czyz, and M. Stepnik Cancer Chemother. Pharmacol. 61 2008 727 737
31. H. Mizutani Yakugaku Zasshi 127 2007 1837 1842
32. P. Huang, L. Feng, E.A. Oldham, M.J. Keating, and W. Plunkett Nature 407 2000 390 395
33. D.A. Gewirtz Biochem. Pharmacol. 57 1999 727 741
34. M.R. McCall, and B. Frei Free Radic. Biol. Med. 26 1999 1034 1053
35. M. Dizdaraglu Free Radic. Biol. Med. 10 1991 225 242
36. E.S. Henle, and S. Linn J. Biol. Chem. 272 1997 19095 19098
37. T. Mosmann J. Immunol. Methods 65 1983 55 63
38. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265 275
39. E.D. Paglia, and W.N. Valentine J. Lab. Clin. Med. 70 1967 158 169
40. H. Aebi Catalase New York Method of Enzymatic Analysis Academic vol. 2 1984 673 684
41. S. Marklund, and G. Marklund Eur. J. Biochem. 47 1974 469 474
42. G.L. Ellman Arch. Biochem. Biophys. 82 1959 70 77
43. S.P. Wolf Meth. Enzymol. 233 1994 182 189
44. T. Zhou, G. Zhou, W. Song, N. Eguchi, W. Lu, E. Lundin, T. Jim, and G. Nordberg Toxicology 142 1999 1 3