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Synthesis and potent cytotoxicity of some novel imidazopyridine derivatives against MCF-7 human breast adenocarcinoma cell line

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Chemistry of Heterocyclic Compounds Aims and scope

A series of novel 2-phenyl-3H-imidazo[4,5-b]pyridines and 2-phenyl-3H-imidazo[4,5-c]pyridines and their precursors were synthesized. Their in vitro cytotoxicity against MCF-7 human breast adenocarcinoma cell line has been investigated, and some of the tested compounds have shown high cytotoxic activity against MCF-7 cells. N-Hydroxy-4-(3H-imidazo[4,5-b]pyridin-2-yl)benzenecarboximidamide was the most active compound with IC50 equal to 0.082 μM, which is an activity almost as high as that of a commonly used anticancer drugs docetaxel and imatinib mesylate.

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References

  1. Thurston, D. E. Chemistry and Pharmacology of Anticancer Drugs, 2nd ed.; CRC Press: Boca Raton, 2013.

    Google Scholar 

  2. Hranjec, M.; Lučić, B.; Ratkaj , I.; Pavelić, S. K.; Piantanida, I.; Pavelić, K.; Karminski-Zamola, G. Eur. J. Med. Chem. 2011, 46, 2748.

    Article  CAS  Google Scholar 

  3. Zhang, M.; Yogesha, S. D.; Mayfield, J. E.; Gill, G. N.; Zhang, Y. Febs J. 2013, 280, 4739.

    Article  CAS  Google Scholar 

  4. Lukasik, P. M.; Elabar, S.; Lam, F.; Shao, H.; Liu, X.; Abbas, A.Y.; Wang, S. Eur. J. Med. Chem. 2012, 57, 311.

    Article  CAS  Google Scholar 

  5. Bavetsias, V.; Sun, C.; Bouloc, N.; Reynisson, J.; Workman, P.; Linardopoulos, S.; McDonald, E. Bioorg. Med. Chem. Lett. 2007, 17, 6567.

    Article  CAS  Google Scholar 

  6. Bavetsias, V.; Large, J. M.; Sun, C.; Bouloc, N.; Kosmopoulou, M.; Matteucci, M.; Wilsher, N. E.; Martins, V.; Reynisson, J.; Atrash, B.; Faisal, A.; Urban, F.; Valenti, M.; de Haven Brandon, A.; Box, G.; Raynaud, F. I.; Workman, P.; Eccles, S. A.; Bayliss, R.; Blagg, J.; Linardopoulos, S.; McDonald, E. J. Med. Chem. 2010, 53, 5213.

    Article  CAS  Google Scholar 

  7. Bavetsias, V.; Crumpler, S.; Sun, C.; Avery, S.; Atrash, B.; Faisal, A.; Moore, A. S.; Kosmopoulou, M.; Brown, N.; Sheldrake, P. W.; Bush, K.; Henley, A.; Box, G.; Valenti, M.; de Haven Brandon, A.; Raynaud, F. I.; Workman, P.; Eccles, S. A.; Bayliss, R.; Linardopoulos, S.; Blagg, J. J. Med. Chem. 2012, 55, 8721.

    Article  CAS  Google Scholar 

  8. Bavetsias, V.; Faisal, A.; Crumpler, S.; Brown, N.;Kosmopoulou, M.; Joshi, A.; Atrash, B.; Pérez-Fuertes, Y.; Schmitt, J. A.; Boxall, K. J.; Burke, R.; Sun, C.; Avery, S.; Bush, K.; Henley, A.; Raynaud, F. I.; Workman, P.; Bayliss, R.; Linardopoulos, S.; Blagg, J. J. Med. Chem. 2013, 56, 9122.

    Article  CAS  Google Scholar 

  9. Wang, T.; Block, M. A.; Cowen, S.; Davies, A. M.; Devereaux, E.; Gingipalli, L.; Johannes, J.; Larsen, N. A.; Su, Q.; Tucker, J. A.; Whitston, D.; Wu, J.; Zhang, H. J.; Zinda, M.; Chuaqui, C. Bioorg. Med. Chem. Lett. 2012, 22, 2063.

    Article  CAS  Google Scholar 

  10. Johannes, J. W.; Chuaqui, C.; Cowen, S.; Devereaux, E.; Gingipalli, L.; Molina, A.; Wang, T.; Whitston, D.; Wu, X.; Zhang, H.-J.; Zinda, M. Bioorg. Med. Chem. Lett. 2014, 24, 1138.

    Article  CAS  Google Scholar 

  11. Cho, Y. S.; Angove, H.; Brain, C.; Chen, C. H.-T.; Cheng, H.; Cheng, R.; Chopra, R.; Chung, K.; Congreve, M.; Dagostin, C.; Davis, D. J.; Feltell, R.; Giraldes, J.; Hiscock, S. D.; Kim, S.; Kovats, S.; Lagu, B.; Lewry, K.; Loo, A.; Lu, Y.; Luzzio, M.; Maniara, W.; McMenamin, R.; Mortenson, P. N.; Benning, R.; O'Reilly, M.; Rees, D. C.; Shen, J.; Smith, T.; Wang, Y.; Williams, G.; Woolford, A. J. A.; Wrona, W.; Xu, M.; Yang, F.; Howard, S. ACS Med. Chem. Lett. 2012, 3, 445.

    Article  CAS  Google Scholar 

  12. Chen, D.; Wang, Y.; Ma, Y.; Xiong, B.; Ai, J.; Chen, Y.; Geng, M.; Shen, J. Chem Med Chem. 2012, 7, 1057.

    Article  CAS  Google Scholar 

  13. Munde, M.; Kumar, A.; Peixoto, P.; Depauw, S.; Ismail, M. A.; Farahat, A. A.; Paul, A.; Say, M. V.; David-Cordonnier, M.-H.; Boykin, D. W.; Wilson, W. D. Biochemistry 2014, 53, 1218.

    Article  CAS  Google Scholar 

  14. Paul, A.; Bhattacharya, S. Curr. Sci. 2012, 102, 212.

    CAS  Google Scholar 

  15. Baraldi, P.G.; Bovero, A.; Fruttarolo, F.; Preti, D.; Tabrizi, M. A.; Pavani, M. G.; Romagnoli, R. Med. Res. Rev. 2004, 24, 475.

    Article  CAS  Google Scholar 

  16. Karataş, H.; Alp, M.; Yildiz, S.; Göker, H. Chem. Biol. Drug. Res. 2012, 80, 237.

    Article  Google Scholar 

  17. Püsküllü, M. O.; Yildiz, S.; Duydu, Y.; Üstündag, A. J. Enzyme Inhib. Med. Chem. 2015, 30, 173.

    Article  Google Scholar 

  18. Rice, C. A.; Colon, B. L.; Alp, M.; Göker H.; Boykin, D. W.; Kyle, D. E. Antimicrob. Agents Chemother. 2015, 59, 2037.

    Article  CAS  Google Scholar 

  19. Ridley, H. F.; Spickett, R. G. W.; Timmis, G. M. J. Heterocycl. Chem. 1965, 2, 456.

    Article  Google Scholar 

  20. Khanna, I. K.; Weier, R. M,; Lentz, K. T.; Swenton, L.; Lankin, D. C. J. Org. Chem. 1995, 60, 960

    Article  CAS  Google Scholar 

  21. Zelenin, K. N.; Ukraintsev, I. V.; Alekseev, V. V. Chem. Heterocycl. Compd. 1998, 34, 329. [Khim. Geterotsikl. Soedin. 1998, 363.]

  22. Suzuki, H.; Ohashi, M.; Itoh, K.; Matsuda, I.; Ishii, Y. Bull. Chem. Soc. Jpn. 1975, 48, 1922.

    Article  CAS  Google Scholar 

  23. Yu, J.; Lu, M. Synth. Commun. 2014, 44, 2520.

    Article  CAS  Google Scholar 

  24. Lipunova, G. N.; Nosova, E. V.; Charushin, V. N. Chem. Heterocycl. Compd. 2014, 50, 764. [Khim. Geterotsikl. Soedin. 2014, 831.]

  25. Roger, R. Neilson, D. Chem. Rev. 1961, 61, 179.

    Article  CAS  Google Scholar 

  26. Mosmann, T. J. Immunol. Methods 1983, 65, 55.

    Article  CAS  Google Scholar 

  27. Kuźma, Ł.; Wysokińska, H.; Różalski, M.; Krajewska, U.; Kisiel, W. Fitoterapia 2012, 83, 770.

    Article  Google Scholar 

  28. Malamas, M. S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W.; McDevitt, R.; Adebayo, F. O.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Taylor, J. R. J. Med. Chem. 2000, 43, 1293.

    Article  CAS  Google Scholar 

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The Central Laboratory of Ankara University, Faculty of Pharmacy, provided support for the acquisition of the NMR and mass spectra and elemental analysis.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, 38039, Kayseri, Turkey

    Mustafa Orhan Püsküllü

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, 06100, Tandogan, Ankara, Turkey

    Cigdem Karaaslan & Hakan Göker

  3. Department of Biochemistry, Faculty of Pharmacy, Ankara University, 06100, Tandogan, Ankara, Turkey

    Filiz Bakar

Authors
  1. Mustafa Orhan Püsküllü
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  2. Cigdem Karaaslan
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  3. Filiz Bakar
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  4. Hakan Göker
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Correspondence to Hakan Göker.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(8), 723–733

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Püsküllü, M.O., Karaaslan, C., Bakar, F. et al. Synthesis and potent cytotoxicity of some novel imidazopyridine derivatives against MCF-7 human breast adenocarcinoma cell line. Chem Heterocycl Comp 51, 723–733 (2015). https://doi.org/10.1007/s10593-015-1765-7

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  • DOI: https://doi.org/10.1007/s10593-015-1765-7

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