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Research Article

Synthesis and potential antitumor activity of 7-(4-substituted piperazin-1-yl)-4-oxoquinolines based on ciprofloxacin and norfloxacin scaffolds: in silico studies

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Pages 796-809 | Received 30 Apr 2015, Accepted 30 May 2015, Published online: 30 Jul 2015

References

  • Avendaño C, Menéndez JC. Medicinal chemistry of anticancer drugs. Amsterdam, Netherlands: Elsevier; 2008
  • Harris CC, Hollstein M. Clinical implications of the p53 tumor-suppressor gene. N Engl J Med 1993;329:1318–27
  • Varmus H. The new era in cancer research. Science 2006;312:1162–5
  • Eckhardt S. Recent progress in the development of anticancer agents. Curr Med Chem 2002;2:419–39
  • Hooper DC, Rubinstein E. Quinolone antimicrobial agents. Washington, USA: ASM Press American Society for Microbiology; 2003
  • (a) Abdel-Aziz AA-M, Asiri YA, Al-Agamy MHM. Design, synthesis and antibacterial activity of fluoroquinolones containing bulky arenesulfonyl fragment: 2D-QSAR and docking study. Eur J Med Chem 2011;46:5487–97. (b) Nieto MJ, Alovero FL, Manzo RH, Mazzieri MR. A new class of fluoroquinolones: benzenesulfonamidefluoroquinolones (BSFQs), antibacterial activity and SAR studies. Eur J Med Chem 1999;34:209–14. (c) Nieto MJ, Alovero FL, Manzo RH, Mazzieri MR. Benzenesulfonamide analogs of fluoroquinolones. Antibacterial activity and QSAR studies. Eur J Med Chem 2005;40:361–9. (d) Alovero F, Barnes A, Nieto M, et al. Comparative study of new benzenesulphonamide fluoroquinolones structurally related to ciprofloxacin against selected ciprofloxacin-susceptible and -resistant Gram-positive cocci. J Antimicrob Chemother 2001;48:709–12
  • Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC. Synthesis and antibacterial evaluation of certain quinolone derivatives. J Med Chem 2001;44:2374–7
  • Mirzaei M, Foroumadi A. Synthesis and in-vitro antibacterial activity of N-piperazinyl quinolone derivatives with a 2-thienyl group. Pharm Pharm Commun 2000;6:351–4
  • Hooper DC. Mechanisms of action of antimicrobials: focus on fluoroquinolones. Clin Infect Dis 2001;32:S9–15
  • Blondeau JM. Fluoroquinolones: mechanism of action, classification, and development of resistance. Surv Ophtalmol 2004;49:S73–8
  • Anderson VE, Osheroff N. Type II topoisomerases as targets for quinolone antibacterials: turning Dr. Jekyll into Mr. Hyde. Curr Pharm Des 2001;7:337–53
  • Alovero F, Pan XS, Morris J, et al. Engineering the specificity of antibacterial fluoroquinolones: benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase. Antimicrob Agents Chemother 2000;44:320–5
  • Pan XS, Hamlyn P, Talens-Visconti R, et al. Small-colony mutants of Staphylococcus aureus allow selection of gyrase-mediated resistance to dual-target fluoroquinolones. Antimicrob Agents Chemother 2002;46:2498–506
  • Heddle J, Maxwell A. Quinolone-binding pocket of DNA gyrase: role of GyrB. Antimicrob Agents Chemother 2002;46:1805–15
  • Fang KC, Chen YL, Sheu JY, et al. Synthesis, antibacterial, and cytotoxic evaluation of certain 7-substituted norfloxacin derivatives. J Med Chem 2000;43:3809–12
  • Azéma J, Guidetti B, Dewelle J, et al. 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: synthesis and in vitro biological evaluation as potential antitumor agents. Bioorg Med Chem Lett 2009;17:5396–407
  • Yamashita Y, Ashizawa T, Morimoto M, et al. Antitumor quinolones with mammalian topoisomerase II mediated DNA cleavage activity. Cancer Res 1992;52:2818–22
  • Paul M, Gafter-Gvili A, Fraser A, Leibovici L. The anti-cancer effects of quinolone antibiotics. Eur J Clin Microbiol Infect Dis 2007;26:825–31
  • Herold C, Ocker M, Ganslmayer M, et al. Ciprofloxacin induces apoptosis and inhibits proliferation of human colorectal carcinoma cells. Br J Cancer 2002;86:443–8
  • El-Rayes BF, Grignon R, Aslam N, et al. Ciprofloxacin inhibits cell growth and synergises the effect of etoposide in hormone resistant prostate cancer cells. Int J Oncol 2002;21:207–11
  • Yamakuchi M, Nakata M, Kawahara K, et al. New quinolones, ofloxacin and levofloxacin, inhibit telomerase activity in transitional cell carcinoma cell lines. Cancer Lett 1997;119:213–19
  • Advani RH, Hurwitz HI, Gordon MS, et al. Voreloxin, a first-in-class anticancer quinolone derivative, in relapsed/refractory solid tumors: a report on two dosing schedules. Clin Cancer Res 2010;16:2167–75
  • Hawtin RE, Stockett DE, Byl JA, et al. Voreloxin is an anticancer quinolone derivative that intercalates DNA and poisons topoisomerase II. PLoS One 2010;5:e10186
  • Abdel-Aziz AA-M, El-Azab AS, Alanazi AM, et al. 7-substituted piperazin-1-yl fluoroquinolone compounds, their use in the treatment of cancer, pharmaceutical compositions and a method for preparation. EPO patent application pending No.: EP 14181731.2, filing date: August 21, 2014
  • (a) Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol 1992;19:622--38. (b) Monks A, Scudiero D, Skehan PJ. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. Natl Cancer Inst 1991;83:757–66. (c) Boyd MR, Paull KD. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev Res 1995;34:91–109
  • Le VM, Wang JJ, Yuan M, et al. An investigation of antitumor efficiency of novel sustained and targeted 5-fluorouracil Nanoparticles. Eur J Med Chem 2015;92:882–9
  • Barlesi F, Tchouhadjian C, Doddoli C, et al. Gefitinib (ZD1839, Iressa) in non-small-cell lung cancer: a review of clinical trials from a daily practice perspective. Fundam Clin Pharmacol 2005;19:385–93
  • Arteaga CL, Johnson DH. Tyrosine kinase inhibitors-ZD1839 (Iressa). Curr Opin Oncol 2001;13:491–8
  • Baker AJ, Gibson KH, Grundy W, et al. Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg Med Chem Lett 2001;11:1911–14
  • Ganjoo KN, Wakelee H. Review of erlotinib in the treatment of advanced non-small cell lung cancer. BiolTargets Therapy 2007;1:335–46
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2001;46:3–26
  • Clark DE, Pickett SD. Computational methods for the prediction of ‘drug-likeness’. Drug Discov Today 2000;5:49–58
  • El-Azab AS, Al-Omar MA, Abdel-Aziz AA-M, et al. Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: molecular docking study. Eur J Med Chem 2010;45:4188–98
  • Moda TL, Torres LG, Carrara AE, Andricopulo AD. PK/DB: database for pharmacokinetic properties and predictive in silico ADME models. Bioinformatics 2008;24:2270–1
  • El-Deeb IM, Bayoumi SM, El-Sherbeny MA, Abdel-Aziz AA-M. Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction. Eur J Med Chem 2010;45:2516–30
  • Tetko IV. Computing chemistry on the web. Drug Discov Today 2005;10:1497–500
  • Ghose AK, Viswanadhan VN, Wendoloski JJ. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1999;1:55–68

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