Synthesis, characterization of some benzazoles bearing pyridine moiety: Search for novel anticancer agents

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 4025-4034

  Elzahabi, Heba S A ^a  

^a Al Azhar University   (Egypt)

Author keywords

Anti tumor activity; Benzimidazoles; Benzothiazoles; Michael addition

Indexed keywords

(5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL)ACETONITRILE; 1,3 BENZOTHIAZOL 2 YLACETONITRILE; 3 [2 (CYANOMETHYL) 5,6 DIMETHYL 1H BENZIMIDAZOL 1 YL] 3 OXOPROPANENITRILE; 6 AMINO 4 (4 CHLOROPHENYL) 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (1,3 BENZOTHIAZOL 2 YL) 4 (4 HYDROXYPHENYL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (1,3 BENZOTHIAZOL 2 YL) 4 (4 METHOXYPHENYL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (1,3 BENZOTHIAZOL 2 YL) 4 (FURAN 2 YL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (1,3 BENZOTHIAZOL 2 YL) 4 (THIOPHEN 2 YL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL) 4 (4 HYDROXY PHENYL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL) 4 (4 METHOXY PHENYL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL) 4 (FURAN 2 YL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL) 4 (THIOPHEN 2 YL)PYRIDINE 3 CARBONITRILE; 6 AMINO 5 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL) 4 PHENYLPYRIDINE 3 CARBONITRILE; [3 (DIMETHYLAMINO) 2 (5,6 DIMETHYL 1H BENZIMIDAZOL 2 YL)PROP 2 ENENITRILE; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; MALONONITRILE; PYRIDINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAIN CANCER; BREAST CANCER; CANCER CELL CULTURE; CHEMICAL REACTION; CLINICAL ARTICLE; COLON CANCER; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; KIDNEY CANCER; LEUKEMIA CELL; LUNG NON SMALL CELL CANCER; MALE; MELANOMA; MICHAEL ADDITION; OVARY CANCER; PROSTATE CANCER;

ANTINEOPLASTIC AGENTS; AZOLES; CELL LINE, TUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80052946477     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.075     Document Type: Article

References (66)

1. E. Sener, I. Yalcin, O. Temiz, I. Oren, A. Akin, and N. Ucarturk IL Farmaco 52 1997 99
2. P. Sharma, A. Kumar, and M. Sharma Eur. J. Med. Chem. 41 2006 833
3. P. Lindberg, P. Nordberg, T. Alminger, A. Brandstrom, and B. Wallmark J. Med. Chem. 29 1986 1327
4. R. Mannhold Drugs Future 10 1985 570
5. S. Nakamura Chem. Pharm. Bull. 3 1955 379
6. R.S. Verma, and S.A. Immam Def. Sci. J. 25 1975 67
7. A. Zeynep, A. Mehmet, K. Canan, Y. Sulhiye, B. Erdem, and G. Hakan Arch. Pharm. Chem. Life Sci. 339 2006 74
8. T. Meral, G. Hakan, E. Rahmiye, E. Recep, K. Engin, and A. Nurten Arch. Pharm. Pharm. Med. Chem. 330 1997 372
9. Z.M. Nofal, H.H. Fahmy, and H.S. Mohamed Arch. Pharm. Res. 25 2002 28
10. A.C. Cuckler, and K.C. Mezey Arzneim. Forsch 16 1966 411
11. A.C. Hollinshead, and P.K. Smith J. Pharmacol. Exp. Ther. 123 1958 54
12. D.C. O'Sullivan, and A.K. Wallis J. Med. Chem. 15 1972 103
13. B. Simone, K. Mariola, G. Agata, K. Zygmunt, E. Henning, L. Paolo, G. Gilles, and S. Frank Arkivoc iii 2009 225
14. R. Zou, K. Ayres, J. Drach, and L. Townsend J. Med. Chem. 39 1996 3477
15. W.W. Kilgore, and E.R. White Bull. Environ. Contam. Toxicol. 5 1970 67
16. B. Maxwell Appl. Microbiol. 21 1971 944
17. N.A. Tikhonova, N.L. Poznanskaya, V.A. Rusakova, S.N. Ivanova, Yu. N. Fadeev, Yu. N. Ivanchenko, N.I. Skvetsov-Shilkovskii, N.N. Melnikov, and G.I. Zhilsova Mikol. Fitopatol. 7 1973 450
18. K.A.M. Walker, A.C. Braemer, S. Hitt, R.E. Jones, and T.R. Mathews J. Med. Chem 21 1978 840
19. C.J. Going, and V.W. Mayer Mut. Res. 343 1995 185
20. C. Tomlin The Pesticide Manual tenth ed. 1994
21. G. Kamlesh, B. Jamie, P. Austin, B. Julie, W. Leslie, and P. Dulal Biochemistry 43 2004 6645
22. O. Seckin, A. Dilek, Y. Sulhiye, and G. Hakan Bioorg. Med. Chem. 13 2005 1587
23. G. Hakan, M. Tuncbilek, G. Ayhan, and N. Altanlar Farmaco 53 1998 415
24. T. Hisano, M. Ichikawa, K. Tsumoto, and M. Tasaki Chem. Pharm. Bull. 30 1982 2996
25. M. Tuncbilek, T. Kiper, and N. Altanlar Eur. J. Med. Chem. 44 2009 1024
26. E.A. Ibrahim, A.M.E. Omar, and M.A. Khalil J. Pharm. Sci. 69 1980 1348
27. A.K. Piskin, A. Zeynep, F.B. Atac, Y. Musdal, and E. Buyukbingol Turk. J. Biochem. 34 2009 39
28. T.A. Heba, A.F.R. Fatma, M.R. Mostafa, and I.E. Hoda Eur. J. Med. Chem. 45 2010 2336
29. Sh. Mohammad, M.M. Abdullah, M.A. Bakht, and M. Jaseela Eur. J. Med. Chem. 45 2010 114
30. N. Boufatah, A. Gellis, J. Maldonado, and P. Vanelle Tetrahedron 60 2004 9131
31. M. Boiani, and M. Gonzalez Mini Rev. Med. Chem. 5 2005 409
32. S. Alper, O. Temiz, E. Sener, and I. Yalcin Il Farmaco 58 2003 497
33. S. Neidle, J. Mann, E.L. Rayner, A. Baron, Y. Opoku-Boahen, I.J. Simpson, N.J. Smith, K.R. Fox, J.A. Hartley, and L.R. Kelland Chem. Commun. 1999 929
34. K. Wong, Recent Patents on Anti-Cancer Drug Discovery, 4, (2009) 28.
35. N.K. Haass, K. Sproesser, T.K. Nguyen, R. Contractor, A. Medina, K.L. Nathanson, M. Herlyn, and K.S.M. Smalley Clin. Cancer Res. 14 2008 230
36. www.chem-x-infinity.com Benzimidazole nucleotide interacting library.
37. Z. Ates, B.C. Eke, S. Suzen, E. Buyukbingol, and M. Iscan Il Farmaco 52 1997 703
38. Z. Ates-Alagoz, and E. Buyukbingol Heterocyclic Commun. 7 2001 455
39. Z. Ates-Alagoz, B.C. Eke, T. Coban, M. Iscan, and E. Buyukbingol Arch. Pharm. 337 2004 188
40. S. Budow, M. Kozlowska, A. Gorska, Z. Kazimierczuk, H. Eickmeier, P. La Colla, G. Gosselin, and F. Seela Arkivoc 2009 225 250
41. M.T. Migawa, J. Girardet, J.A. Walker, G.W. Koszalka, S.D. Chamberlain, J.C. Drach, and L.B. Townsend J. Med. Chem. 41 1998 1242 1251
42. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, and L.B. Townsend J. Med. Chem. 41 1998 1252 1262
43. 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
44. A. Pinar, P. Yurdakul, I. Yildiz, O. Temiz-Arpaci, N.L. Acan, E. Aki-Sener, and I. Yalcin Biochem. Biophys. Res. Commun. 317 2004 670 674
45. H.M. Refaat Eur. J. Med. Chem. 45 2010 2949 2956
46. T.D. Bradshaw, S. Wrigley, D.F. Shi, R.J. Schulz, K.D. Paull, and M.F.G. Stevens Br. J. Cancer 77 1998 745
47. E. Kashiyama, I. Hutchinson, M.S. Chua, S.F. Stinson, L.R. Phillips, G. Kaur, E.A. Sausville, T.D. Bradshaw, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 42 1999 4172
48. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 44 2001 1446
49. C.K. Lau, C. Dufresne, Y. Gareau, R. Zamboni, M. Labelle, R.N. Young, K.M. Metters, C. Rochette, N. Sawyer, D.M. Slipetz, L. Charette, T. Jones, M. McAuliffe, C. McFarlane, and A.W. Ford-Hutchinson Bioorg. Med. Chem. 5 1995 1615
50. A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, and G.B. Behera Chem. Rev. 100 2000 1973
51. A.S. Michaelidou, and D. Hadjipavlou-Litina Chem. Rev. 105 2005 3235
52. S. Aiello, G. Wells, E.L. Stone, H. Kadri, R. Bazzi, D.R. Bell, M.F.G. Stevens, C.S. Matthews, T.D. Bradshaw, and A.D. Westwell J. Med. Chem. 51 2008 5135
53. Y. Cho, T.R. Ioerger, and J.C. Sacchettini J. Med. Chem. 51 2008 5984
54. S. Prachayasittikul, L. Treeratanapiboon, S. Ruchirawat, and V. Prachayasittikul Excli J. 8 2009 121
55. E. Nassar J. Am. Sci. 6 2010 338
56. S. Koji, K. Satoshi, and N. Yukihiro Synthesis 3 1983 210
57. Y. Ch. Richard, D. Mei-Fang, Ch. Jhao-Yu, L. Chuan-Chen, and L. Shaw-Tao J. Chin. Chem. Soc. 57 2010 213
58. F.S. Babichev, V.K. Patratii, Yu. M. Volovenko, N.G. Prodanckuk, V.G. Sinchenko, and A.G. Nemazanyi Khim. Farm. Zh. 22 1988 1223 Chem. Abstr., 111, (1989) 7285
59. M.E.A. Zaki, A.A. Fadda, K. Samir, and F.A. Amer Chem. Heterocycl. Comp. 39 2003 1242
60. P.A. Thakurdesai, S.G. Wadodkar, and Ch. T. Chopade Pharmacology- Online 1 2007 314
61. K. Bogdanowicz-Szwed, and A. Czarny J. Prakt Chem. 335 1993 279
62. S.N. Kovalenko, M.V. Vasil'ev, I.V. Sorokina, V.P. Chernykh, A.V. Turov, and S.A. Rudnev Chem. Heterocycl. Comp. 34 1998 1412
63. S.M. Rida, S.A.M. El-Hawash, H.T.Y. Fahmy, A.A. Hazzaa, and M.M.M. El-Meligy Arch. Pharm. Res. 29 2006 826
64. A. Monk, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Viagro-Wolff, M. Gray-goodrich, H. Campbell, J. Mayo, and M. Boyd J. Natl. Cancer Inst. 83 1991 757
65. S. Kuo, H. Lee, J. Juang, Y. Lin, T. Wu, J. Chang, D. Lednicer, K. Paull, C.M. Lin, E. Hmel, and K. Lee J. Med. Chem. 36 1993 1146
66. F. Leteurtre, G. Kohlhagen, K. Paull, and Y.J. Pommier J. Natl. Cancer Inst. 86 1994 1239