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Synthesis and antiproliferative activity of combretastatin derivatives with adamantane fragment

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Abstract

The work describes the synthesis of 2-adamantyl 7-[(2-{[(2E)-3-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoyl]amino}ethyl)amino]-7-oxoheptanoate and 7-[(2-{[(2E)-2-(3,4-dimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]amino}ethyl)amino]-7-oxoheptanoate. The latter compound exhibits moderate cytotoxicity (EC50 = 4.8 μmol L–1) against the human epithelial lung carcinoma cells A549.

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References

  1. O. N. Zefirova, E. V. Nurieva, H. Lemcke, A. A. Ivanov, D. V. Shishov, D. G. Weiss, S. A. Kuznetsov, N. S. Zefirov, Bioorg. Med. Chem. Lett., 2008, 18, 5091.

    Article  CAS  Google Scholar 

  2. O. N. Zefirova, E. V. Nurieva, H. Lemcke, A. A. Ivanov, N. V. Zyk, D. G. Weiss, S. A. Kuznetsov, N. S. Zefirov, Mendeleev Commun., 2008, 18, 183.

    Article  CAS  Google Scholar 

  3. O. N. Zefirova, E. V. Nurieva, D. V. Shishov, I. I. Baskin, F. Fuchs, H. Lemcke, F. Schruder, D. G. Weiss, N. S. Zefirov, S. A. Kuznetsov. Bioorg. Med. Chem., 2011, 19, 5529.

    Article  CAS  Google Scholar 

  4. O. N. Zefirova, H. Lemcke, M. Lantow, E. V. Nurieva, B. Wobith, G. E. Onishchenko, A. Hoenen, G. Griffiths, N. S. Zefirov, S. A. Kuznetsov, ChemBioChem., 2013, 14, 1444.

    Article  CAS  Google Scholar 

  5. E. V. Nurieva, A. A. Beloglazkina, D. V. Shishlov, V. V. Gogol, Ya. S. Glazkova, B. Wobith, N. S. Zefirov, S. A. Kuznetsov, O. N. Zefirova, Moscow University Chem. Bull., 2013, 68, 37 [Vestn. Mosk. un-ta. Ser. 2. Khim., 2013, 54, 45].

    Article  Google Scholar 

  6. N. S. Zefirov, Ya. S. Glazkova, I. V. Kuznetsova, E. V. Nurieva, O. N. Zefirova, Moscow University Chem. Bull., 2015, 70, 69 [Vestn. Mosk. un-ta. Ser. 2. Khim., 2015, 56, 85].

    Article  Google Scholar 

  7. O. N. Zefirova, E. V. Nurieva, Ya. S. Glazkova, N. A. Zefirov, A. V. Mamaeva, B. Wobith, V. I. Romanenko, N. A. Lesnaya, E. M. Treschalina, S. A. Kuznetsov, Pharm. Chem. J. (Engl. Transl.), 2014, 48, 373 [Khim. Farm. Zh., 2014, 48, 19].

    Article  CAS  Google Scholar 

  8. O. N. Zefirova, Ya. S. Glazkova, E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva, B. Wobith, N. S. Zefirov, S. A. Kuznetsov, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1126 [Izv. Akad. Nauk, Ser. Khim., 2014, 1126].

    Article  CAS  Google Scholar 

  9. N. H. Nam, Curr. Med. Chem., 2003, 10, 1697.

    Article  CAS  Google Scholar 

  10. T. L. Nguyen, C. McGrath, A. R. Hermone, J. C. Burnett, D. W. Zaharevitz, B. W. Day, P. Wirf, E. Hamel, R. Gussio, J. Med. Chem., 2005, 48, 6107.

    Article  CAS  Google Scholar 

  11. O. N. Zefirova, A. G. Diikov, N. V. Zyk, N. S. Zefirov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 680 [Izv. Akad. Nauk, Ser. Khim., 2007, 655].

    Article  CAS  Google Scholar 

  12. C. Borrel, S. Thoret, X. Cachet, D. Guénard, F. Tillequin, M. Koch, S. Michel, Bioorg. Med. Chem., 2005, 13, 3853.

    Article  CAS  Google Scholar 

  13. K. Gaukroger, J. A. Hadfield, L. A. Hepworth, J. Org. Chem., 2001, 66, 8135.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    E. V. Nurieva, N. A. Zefirov, N. S. Zefirov & O. N. Zefirova

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi pr-d, 142432, Chernogolovka, Moscow Region, Russian Federation

    N. S. Zefirov & O. N. Zefirova

  3. Institute of Biological Sciences, University of Rostock, 18106, Rostock, Germany

    S. A. Kuznetsov

Authors
  1. E. V. Nurieva
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  2. N. A. Zefirov
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  3. N. S. Zefirov
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  4. S. A. Kuznetsov
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  5. O. N. Zefirova
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Corresponding author

Correspondence to O. N. Zefirova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2248–2252, September, 2015.

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Nurieva, E.V., Zefirov, N.A., Zefirov, N.S. et al. Synthesis and antiproliferative activity of combretastatin derivatives with adamantane fragment. Russ Chem Bull 64, 2248–2252 (2015). https://doi.org/10.1007/s11172-015-1146-5

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  • DOI: https://doi.org/10.1007/s11172-015-1146-5

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