A Molecular Docking Study of N-Ferrocenylmethylnitroanilines as Potential Anticancer Drugs
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[1] Ferlay J, Soerjomataram I, Ervik M, Dikshit R, Eser S, Mathers C, Rebelo M, Parkin DM, Forman D, Bray, F. GLOBOCAN 2012 v1. 0, Cancer Incidence and Mortality Worldwide: IARC CancerBase No. 11 [Internet]. Lyon, France: International Agency for Research on Cancer; 2013. Available from: http: /globocan. iarc. fr, accessed on 18/12/(2013).
DOI: https://doi.org/10.1002/ijc.29210[2] Noriaki Okimoto, Kazunori Yamanaka, Junko Ueno, Masayuki Hata, Tyuji Hoshino, Minoru Tsuda. Theoretical Studies of the ATP Hydrolysis Mechanism of Myosin. Biophysical journal, Volume 81, Issue 5, p.2786–2794.
DOI: https://doi.org/10.1016/s0006-3495(01)75921-8[3] Xian-Feng, H.; Ling-Zhu, W.; Long, T.; Ying-Xun, L.; Fan, W.; Guo-Qiang, S.; Ban-Feng, R. Synthesis, characterization and antitumor activity of novel ferrocene derivatives containing pyrazolyl-moiety: Journal of Organometallic Chemistry, 2014, 749(1), 157-162.
DOI: https://doi.org/10.1016/j.jorganchem.2013.08.043[4] Lal, B.; Badshah, A.; Altaf, A.A.; Tahir, M.N.; Ullah, S.; Huq, F. Synthesis, characterization and antitumor activity of new ferrocene incorporated N, N'-disubstituted thioureas: Dalton Trans, 2012, 41(48), 14643-14650.
DOI: https://doi.org/10.1039/c2dt31570j[5] Ornelas, C: Application of ferrocene and its derivatives in cancer research. New J. Chem, 2011, 35, 1973-(1985).
[6] Venkatachalam, T.K.; Mao, C.; Uckun, Fatih.M. Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds: Bioorganic and Medicinal Chemistry, 2004, 12(15), 4275-4284.
DOI: https://doi.org/10.1016/j.bmc.2004.04.050[7] Kondapi, A.K.; Satyanarayana, N.; Saikrishna, A.D. A study of the topoisomerase II activity in HIV-1 replication using the ferrocene derivatives as probes: Arch. Biochem. Biophys, 2006, 450(1), 123-132.
DOI: https://doi.org/10.1016/j.abb.2006.04.003[8] Santos, L.; Lima, L.A.; Filho, V.C.; Correa, R.; Buzzi, F.C.; Nunes, R.J. Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thioureaand urea derivatives with anti-nociceptive activity: Bioorgan. Med. Chem, 2008, 16(18), 8526-8534.
DOI: https://doi.org/10.1016/j.bmc.2008.08.019[9] Sharma, B.K.; Sharma, S. K; Singh P.; Sharma S.A.; Enzym, J. Quantitative structure-activity relationship study of novel, potent, orally active, selective VEGFR-2 and PDGFR alpha tyrosinekinase inhibitors: Derivatives of N-Phenly-N'-{4-(4-quinolyloxy)phenyl) urea as antitumor agents: Inhib Med. Chem, 2008, 23(2): 168-173.
DOI: https://doi.org/10.1080/14756360701450301[10] Struga, M.; Kossakowski, J.; Kedzierska, E.; Fidecka, S.; Stefanska, J. Synthesis and pharmacological activity of urea and thiourea derivatives of 4-azatricyclo [5. 2. 2. 0(2, 6)] undec-8-ene-3, 5-dione: Chem. Pharmaceutical Bulletin 2007, 55(5), 796-799.
DOI: https://doi.org/10.1002/chin.200745198[11] Biot, B.; Francois, N.; Maciejewski, L.; Brocard J.; Poulain, D. Bioorg. Synthesis and antifungal activity of a ferrocene-fluconazole analogue: Bioorg Med Chem Lett, 2000, 10(8): 839-841.
DOI: https://doi.org/10.1016/s0960-894x(00)00120-7[12] Itoh, T.; Shirakami, S.; Ishida, N.; Yamashita, Y.; Yoshida, T.; Kim, H.S.; Wataya, Y. Synthesis of novel ferrocenyl sugars and their antimalarial activities: Bioorg. Med. Chem. Lett, 2000, 10(15), 1657-1659.
DOI: https://doi.org/10.1002/chin.200044216[13] Swarts, J.C.; Vosloo T.G.; Cronge, S.J.; (INA) Du Plessis, W.C.; Van Rensburg, C.E.J.; Kreft, E.; Van Lier, J.E. Cytotoxicity of a Series of Ferrocene-containing β-Diketones. Anticancer research, 2008, 28, 2781-2784.
[14] Acevedo-Morantes C. Y; Meléndez E.; Singh, P.S.; Singh, P.; Ramírez-Vick J.E. Cytotoxicity and Reactive Oxygen Species Generated by Ferrocenium and Ferrocene on MCF7 and MCF10A Cell Lines. J Cancer Sci Ther, 2012, 4(9), 271-275.
DOI: https://doi.org/10.4172/1948-5956.1000154[15] Köpf H.; Köpf-Maier P. Titanocene dichloride—the first metallocene with cancerostatic activity. Angew. Chem., Int. Ed. Engl. 1979, 18, 477–478. [PubMed].
DOI: https://doi.org/10.1002/anie.197904771[16] Köpf-Maier P.; Köpf H. Antitumor metallocene oder ähnlich. Drugs Future 1986, 11, 297–320.
DOI: https://doi.org/10.1358/dof.1986.011.04.237197[17] T. Lanez, M. Henni, Determination of binding parameters of 2-(ferrocenylmethyl-amino)benzonitrile and 3-(ferrocenylmethylamino)benzo-nitrile with 2, 2-diphenyl-1-picrylhydrazyl free radical. J. Fundam. Appl. Sci., 2016, 8 (1) 176-181.
DOI: https://doi.org/10.4314/jfas.v8i1.10[18] B. Vijayakumar and P. Dheen Kumar. Molecular docking studies – a review. IJMCA / Vol 2 / Issue 2/2012/ 106-111.
[19] Lengauer T, Rarey M. Computational methods for biomolecular docking. Curr Opin Struct Biol 1996; 6 (3): 402-406.
[20] Gaba Monika, Gaba Punam, Singh Sarbjot, and Gupta G. D. An overview on molecular docking. Int.J. Drug Dev. & Res., April-June 2010, 2(2): 219-231.
[21] Thomsen R and Mikael C H, J. Med. Chem., 2006; 49: 3315-3321.
[22] Rahim, O.; Khelef, A.; Terki, B.; Sadok, M.M.; Lanez, T. N-Ferrocenylmethyl-2-nitroaniline: Acta Cryst, 2012, E68, m1318.
DOI: https://doi.org/10.1107/s1600536812039177[23] Boubekri, C.; Khelef A.; Terki B.; Lanez, T. Synthesis and Electrochemical Properties of N-(ferrocenylmethyl)aminobenzo-nitrile and N-(ferrocenylmethyl)nitroaniline Derivatives International: Letters of Chemistry, Physics and Astronomy, 2015, 49, 27-34.
DOI: https://doi.org/10.18052/www.scipress.com/ilcpa.49.27[24] HyperChem (Molecular Modeling System) Hypercube, MC, 1115 MV 4thStreet, Gainesville, EL 32601; USA, 2007, http: /www. hyperchem. com.
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