Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 387-398

  El Nakkady, Sally S ^a   Hanna, Mona M ^b   Roaiah, Hanaa M ^a   Ghannam, Iman A Y ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

2 Phenylindoles; Antitumor activity; Breast cancer cell lines MCF 7 and MDA MB 231; Docking study; Indole carboxaldehyde

Indexed keywords

2 (4 HYDROXYPHENYL) 1H INDOLE 3 CARBOXALDEHYDE; 2 (4 HYDROXYPHENYL) 1H INDOLE 3 CARBOXALDEHYDE OXIME; 2 [4 (1H INDOL 2 YL)PHENOXY] 1 (PYRROLIDIN 1 YL)ETHANONE; 2 [4 (1H INDOL 2 YL)PHENOXY] N (PYRAZIN 2 YL)ACETAMIDE; 2 [4 (1H INDOL 2 YL)PHENOXY] N (PYRIDIN 4 YL)ACETAMIDE; 2 [4 (1H INDOL 2 YL)PHENOXY] N' ACETYLACETOHYDRAZIDE; 2 [4 (1H INDOL 2 YL)PHENOXY] N' PHENYLACETOHYDRAZIDE; 2 [4 (1H INDOL 2 YL)PHENOXY] N,N BIS(2 HYDROXYETHYL)ACETAMIDE; 2 [4 (1H INDOL 2 YL)PHENOXY] N,N DIMETHYLACETAMIDE; 2 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]] 1H BENZO[D]IMIDAZOLE; 2 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]] 1H BENZO[D]OXAZOLE; 2 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]] 1H IMIDAZOLE; 2 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]HYDRAZINECARBOTHIOAMIDE; 2 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]PROPANEDINITRILE; 2 AMINO N' [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]BENZOHYDRAZIDE; 2 PHENYLINDOLE DERIVATIVE; 4 (1H INDOL 2 YL)PHENYLMETHYLCARBONATE; 4 [3 [(2 METHYLHYDRAZONO)METHYL] 1H INDOL 2 YL]PHENOL; 4 [3 [(2 PHENYLHYDRAZONO)METHYL] 1H INDOL 2 YL]PHENOL; 4 [3 [[2 (2 CHLOROPHENYL)HYDRAZONO]METHYL] 1H INDOL 2 YL]PHENOL; 4 AMINO N' [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]BENZOHYDRAZIDE; 4 CHLORO N' [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]BENZOHYDRAZIDE; 5 [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE] PYRIMIDINE 2,4,6 (1H,3H,5H)TRIONE; ANTINEOPLASTIC AGENT; METHYL 2 [4 (1H INDOL 2 YL)PHENOXY]ACETATE; N' [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE] 4 NITROBENZOHYDRAZIDE; N' [[2 (4 HYDROXYPHENYL) 1H INDOL 3 YL]METHYLENE]ACETOHYDRAZIDE; N' [[2 (4 HYDROXYPHENYL)1H INDOL 3 YL]METHYLENE] BENZOHYDRAZIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN MCF 7; CHEMICAL REACTION; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOLECULAR DOCKING; SUBSTITUTION REACTION;

ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; COLCHICINE; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; TUBULIN;

EID: 84855816930     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.11.007     Document Type: Article

References (30)

1. G. Bacher, T. Emig, P. Emig, T. Klenner, B. Kutscher, and B. Nickel Pure Appl. Chem. 73 2001 1459 1464
2. B. Bhattacharyya, D. Panda, S. Gupta, and M. Banerjee Med. Res. Rev. 28 2008 155 183
3. E. Pasquier, N. André, and D. Braguer Cancer Drug Targets 7 2007 566 581
4. K. Odlo, J. Hentzen, J.F. dit Chabert, S. Ducki, O.A.B.S.M. Gani, I. Sylte, M. Skrede, V.A. Florenes, and T.V. Hansen Bioorg. Med. Chem. 16 2008 4829 4838
5. A. Jordan, J.A. Hadfield, N.J. Lawrence, and A.T. McGown Med. Res. Rev. 18 1998 259 296
6. K.D. Tripathi Essentials of Medical Pharmacology 2003 Jaypee New Delhi (Chapter 60)
7. E.R. El-Sawy, F.A. Bassyouni, S.H. Abu-Bakr, H.M. Rady, and M.M. Abdlla Acta Pharm. 60 2010 55 71
8. N. Ziedan, F. Stefanelli, S. Fogli, and A. Westwell Eur. J. Med. Chem. 45 2010 4523 4530
9. S. Mahboobi, A. Sellmer, E. Eichhorn, T. Beckers, H. Fiebig, and G. Kelter Eur. J. Med. Chem. 40 2005 85 92
10. B.G. Trogden, S.H. Kim, S. Lee, and J.A. Katzenellenbogen Bioorg. Med. Chem. Lett. 19 2009 485 488
11. T. Golob, R. Liebl, and E. von Angerer Bioorg. Med. Chem. 10 2002 3941 3953
12. E. von Angerer, C. Biberger, E. Holler, R. Koop, and S. Leichtl Biochem. Mol. Biol. 49 1994 51 62
13. R. Mohan, M. Banerjee, A. Ray, T. Manna, L. Wilson, T. Owa, B. Bhattacharyya, and D. Panda Biochemistry 45 2006 5440 5449
14. R. Gatspar, M. Goldbrunner, D. Marko, and E. von Angerer J. Med. Chem. 41 1988 4965 4972
15. D. Kaufmann, M. Pojarová, S. Vogel, R. Liebl, R. Gastpar, D. Gross, T. Nishino, T. Pfaller, and E. von Angerer Bioorg. Med. Chem. 15 2007 5122 5136
16. M. Pojarová, D. Kaufmann, R. Gastpar, T. Nishino, P. Reszka, P. Bednarski, and E. von Angerer Bioorg. Med. Chem. 15 2007 7368 7379
17. S. Vogel, D. Kaufmann, M. Pojarová, C. Müller, T. Pfaller, S. Kühne, P. Bednarski, and E. von Angerer Bioorg. Med. Chem. 16 2008 6436 6447
18. S.Y. Liao, L. Qian, T.F. Miao, H.L. Lu, and K.C. Zheng Eur. J. Med. Chem. 44 2009 2822 2827
19. M. Smith, and J. March Advanced Organic Chemistry: Reactions, Mechanisms and Structure fifth ed. 2000 John Wiley and Sons New York pp. 1824
20. A. Ames, D. Ames, C. Coyne, T. Grey, I. Lockhart, and R. Ralph J. Chem. Soc. 685 1959 3388 3400
21. G.F. Smith J. Chem. Soc. 1954 3842 3845
22. P. Charles, D. de Fillain, N. Souli, L. Blay, J. Labaz, Ger. Offen. 2,526,317 (Cl. C07D, C08K), (08/01/1976), Fr. Appl. 74 21,042, (18/06/1974) 38
23. Chem. Abstr. 48 1976 164604k
24. Z. Nofal, M. El-Zahar, M. Salm, H. Madkour, and S. Abd El-Karim Egypt. J. Chem. 48 2005 587 604
25. M. Radwan, and M. El-Sherbiny Bioorg. Med. Chem. 15 2007 1206 1211
26. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, M. Boyd, and J. Natl Cancer Inst. 83 1991 757 766
27. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. Warren, H. Bokesch, S. Kenney, and M. Boyd J. Natl. Cancer Inst. 82 1990 1107 1112
28. J.J. Arbildua, J.E. Brunett, D.M. Jameson, M. Lopez, E. Nova, R. Lagos, and O. Monasterio Protein Sci. 15 2006 410 419
29. S.L. Mooberry, K.N. Weiderhold, S. Dakshanamurthy, E. Hamel, E.J. Banner, A. Kharlamova, J. Hempel, J.T. Gupton, and M.L. Brown Mol. Pharmacol. 72 2007 132 140
30. G. La Regina, M.C. Elder, A. Brancale, S. Kandil, A. Coluccia, F. Piscitelli, E. Hamel, G. De Martino, R. Matesanz, J.F. Diaz, A.I. Scovassi, E. Prosperi, A. Lavecchia, E. Novellino, M. Artico, and R. Silvestri J. Med. Chem. 50 2007 2865 2874