Part I: Synthesis, cancer chemopreventive activity and molecular docking study of novel quinoxaline derivatives

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 327-340

  Galal, Shadia A ^a   Abdelsamie, Ahmed S ^a   Tokuda, Harukuni ^b   Suzuki, Nobutaka ^b   Lida, Akira ^c   Elhefnawi, Mahmoud M ^a   Ramadan, Raghda A ^a   Atta, Mona H E ^a   El Diwani, Hoda I ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b KANAZAWA UNIVERSITY   (Japan)

^c KINKI UNIVERSITY   (Japan)

Author keywords

12 O Tetradecanoylphorbol 13 acetate (TPA); Anti tumor promoter; Docking; Epstein Barr virus; Protein tyrosine kinase receptor (PTK); Quinoxalines; Synthesis; Two stage carcinogenesis

Indexed keywords

1 ALLYL 3 (2 BENZYLIDENEHYDRAZINYL)QUINOXALIN 2(1H) ONE; 1 ALLYL 3 [1 ALLYL 2 (2 METHOXYBENZYLIDENE)HYDRAZINYL]QUINOXALIN 2(1H) ONE; 1 ALLYL 3 [2 (2 METHOXYBENZYLIDENE)HYDRAZINYL]QUINOXALIN 2(1H) ONE; 2 (1H BENZO[D]IMIDAZOL 2 YLTHIO) 3 CHLOROQUINOXALINE; 2 (3 CHLOROQUINOXALIN 2 YLTHIO) 4 (4 FLUOROPHENYL) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 2 (3 CHLOROQUINOXALIN 2 YLTHIO) 4 (4 HYDROXYPHENYL) 6 OXO 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 2 (3 CHLOROQUINOXALIN 2 YLTHIO) 6 OXO 4 PHENYL 1,6 DIHYDROPYRIMIDINE 5 CARBONITRILE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLTHIO] 3 CHLOROQUINOXALINE; 3 (2 BENZYLIDENEHYDRAZINYL)QUINOXALIN 2(1H) ONE; 3 [2 (2 METHOXYBENZYLIDENE)HYDRAZINYL]QUINOXALIN 2(1H) ONE; 3 HYDRAZINYLQUINOXALIN 2(1H) ONE; ANTINEOPLASTIC AGENT; BENZO[1',2']IMIDAZO[4,5 B]QUINOXALINE; DIMETHYLBENZ[A]ANTHRACENE; EPSTEIN BARR VIRUS ANTIGEN; ETHYL 2 [3 (2 BENZYLIDENEHYDRAZINYL) 2 OXOQUINOXALIN 1(2H) ONE YL]ACETIC ACID; ETHYL 2 [3 [1 (2 ETHOXY 2 OXOETHYL) 2 (2 METHOXYBENZYLIDENE)HYDRAZINYL]QUINOXALIN 1(2H) ONE YL]ACETIC ACID; ETHYL 2 [3 [2 (2 METHOXYBENZYLIDENE)HYDRAZINYL]QUINOXALIN 1(2H) ONE YL]ACETIC ACID; OLEANOLIC ACID; PHORBOL 13 ACETATE 12 MYRISTATE; PROTEIN TYROSINE KINASE INHIBITOR; QUINOXALINE DERIVATIVE; QUINOXALINO[2,3 D]BENZO[B]IMIDAZOLIUM CHLORIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER INHIBITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOUSE; NONHUMAN; PAPILLOMA; SKIN CARCINOGENESIS;

ANIMALS; ANTIGENS, VIRAL; ANTINEOPLASTIC AGENTS; BINDING SITES; DRUG DESIGN; FEMALE; HYDROGEN BONDING; MICE; MODELS, MOLECULAR; NEOPLASMS; PROTEIN CONFORMATION; PROTO-ONCOGENE PROTEINS C-KIT; QUINOXALINES; REPRODUCIBILITY OF RESULTS;

EID: 78650510028     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.022     Document Type: Article

References (39)

1. S. Eckhardt Curr. Med. Chem. Anti Canc. Agents 2 2002 419 439
2. N. Neamati, U.S. Pat. Appl. Publ. 235, 034, 2006.
3. Y. Hu, F. Jiang, B. Yang, Q. He, Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1,951,923 Appl. 10,154,536, 2006.
4. S.T. Hazeldine, L. Polin, J. Kushner, K. White, N.M. Bouregeois, B. Crantz, E. Palomino, T.H. Corbett, and J.P. Horwitz J. Med. Chem. 45 2002 3130 3137
5. J. P. Horwitz, S.T. Hazeldine, T.H. Corbett, L. Polin, WO Patent 03/011832, 2003.
6. S.D. Undevia, F. Innocenti, J. Ramirez, L. House, A.A. Desai, L.A. Skoog, D.A. Singh, T. Karrison, H.L. Kindler, and M.J. Ratain Eur. J. Cancer 44 2008 1684 1692
7. S. Khier, C. Deleuze-Masquéfa, G. Moarbess, F. Gattacceca, D. Margout, I. Solassol, J.-F. Cooperd, F. Pinguet, P.-A. Bonnet, and F.M.M. Bressolle Eur. J. Pharm. Sci. 39 2010 23 29
8. G. Marverti, A. Ligabue, G. Paglietti, P. Corona, S. Piras, G. Vitale, D. Guerrieri, R. Luciani, M.P. Costi, C. Frassineti, and M.S. Moruzzi Eur. J. Pharmacol. 615 2009 17 26
9. S. Hazeldine, L. Polin, J. Kushner, J. Paluch, K. White, M. Edelstein, E. Palomino, T.H. Corbett, and J.P. Horwitz J. Med. Chem. 44 2001 1758 1776
10. S.T. Hazeldine, L. Polin, J. Kushner, K. White, T.H. Corbett, J. Biehl, and J.P. Horwitz Bioorg. Med. Chem. 13 2005 1069 1081
11. A. Levitzki Acc. Chem. Res. 36 2003 462 469
12. J. Lennartsson, O. Voytyuk, E. Heiss, C. Sundberg, J. Sun, and L. Rönnstrand Cancer Ther. 3 2005 5 28
13. I. Posner, and A. Levitzki FEBS Lett. 353 1994 155 161
14. M. Sattler, and R. Salgia Leuk. Res. 28S1 2004 S11 S20
15. T.M. Kolb, and M.A. Davis Toxicol. Sci. 81 2004 233 242
16. C.A. Obafemi, and W. Pfleiderer Helv. Chim. Acta 77 1994 1549 1556
17. W.C. Lumma Jr., W.C. Randall, E.L. Cresson, J.R. Huff, R.D. Hartam, and T.F. Lyon J. Med. Chem. 26 1983 357 363
18. A. McKillop, S.K. Chattopadhyay, A. Henderson, and C. Avendano Synthesis 3 1997 301 304
19. A. McKillop, A. Henderson, P.S. Ray, C. Avendano, and E.G. Molinero Tetrahedron Lett. 23 1982 3357 3360
20. É Csikós, C. Gönczi, B. Podányi, G. Tóth, and I. Hermecz J. Chem. Soc. Perkin Trans. 1 1999 1789 1793
21. O.O. Ajani, C.A. Obafemi, O.C. Nwinyi, and D.A. Akinpelu Bioorg. Med. Chem. 18 2010 214 221
22. P.A. Petyunin, and A.M. Choudry Khim. Geterotsikl. Soedin. 1982 684 686
23. Z.A. Pankina, and M.N. Shchukina Khim. Farmats. Zh. 8 1969 15
24. S.A. Galal, K.H. Hegab, A.S. Kassab, M.L. Rodriguez, S.M. Kerwin, A.A. El-Khamry, and H.I. El Diwani Eur. J. Med. Chem. 44 2009 1500 1508
25. Q.P. Peterson, D.C. Hsu, D.R. Goode, C.J. Novotny, R.K. Totten, and P.J. Hergenrother J. Med. Chem. 52 2009 5721 5731
26. S. Parra, F. Laurent, G. Subra, C. Deleuze-Masquefa, V. Benezecha, J.-R. Fabreguettes, J.-P. Vidal, T. Pocock, K. Elliott, R. Small, R. Escale, A. Michel, J.-P. Chapat, and P.-A. Bonnet Eur. J. Med. Chem. 36 2001 255 264
27. H.T. Abdel-Mohsen, F.A.F. Ragab, M.M. Ramla, and H.I. Diwani Eur. J. Med. Chem. 45 2010 2336 2344
28. A.T. Mavrova, K.K. Anichina, D.I. Vuchev, J.A. Tsenov, M.S. Kondeva, and M.K. Micheva Bioorg. Med. Chem. 13 2005 5550 5559
29. F. Gümüscedil, Pamuka, T. Özden, S. Yldz, N. Diril, E. Öksüzolu, S. Gür, and A. Özkul J. Inorg. Biochem. 94 2003 255 262
30. Y. Ito, M. Kawanishi, T. Harayama, and S. Takabayashi Cancer Lett. 12 1981 175 180
31. M. Takasaki, T. Konoshima, S. Kuroki, H. Tokuda, and H. Nishino Cancer Lett. 173 2001 133 138
32. T. Konoshima, M. Takasaki, M. Kozuka, and H. Tokuda J. Nat. Prod. 50 1987 1167 1170
33. M. Andrzejewska, L. Yépez-Mulia, R. Cedillo-Rivera, A. Tapia, L. Vilpo, J. Vilpo, and Z. Kazimierczuk Eur. J. Med. Chem. 37 2002 973 978
34. M. Saitoh, T. Uemura, Y. Kawasaki, J. Monmma, Y. Matsushima, K. Sakemi, K. Isama, S. Kitajima, Y. Ogawa, R. Hasegawa, T. Suzuki, M. Hayashi, T. Inoue, Y. Ohno, T. Sofuni, Y. Kurokawa, and M. Tsuda Food Chem. Toxicol. 37 1999 777 787
35. M. Takasaki, T. Konoshima, M. Kozuka, H. Tokuda, J. Takayasu, H. Nishino, M. Miyakoshi, K. Mizutani, and K. Lee Bioorg. Med. Chem. 17 2009 600 605
36. E. Abele, R. Abele, P. Arsenyan, S. Belyakov, M. Veveris, and E. Lukevics Chem. Heterocycl. Comp. 43 2007 220 224
37. Y. Lin J. Appl. Cryst. 41 2008 476 478
38. E. Rossmanith J. Appl. Cryst. 39 2006 916 917
39. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Cryst. 27 1994 435 436