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Synthesis of adamantyl-containing cidofovir analogs as potential antiviral prodrugs with high bioavailability parameters

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Abstract

We report on preparation of potential nucleoside phosphonate prodrugs: 1-{3-hydroxy-2-[O-(adamantylalkyl)phosphorylmethoxy]propyl}cytosines containing two structural fragments providing antiviral activity, nucleoside phosphonate and adamantyl sites.

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References

  1. De Clercq, E., Adv. Pharmacol., 2013, vol. 67, p. 293. DOI: 10.1016/B978-0-12-405880-4.00008-1.

    Article  Google Scholar 

  2. De Clercq, E., Antiviral Res., 2007, vol. 75, no. 1, p. 1. DOI: 10.1016/j.antiviral.2006.10.006.

    Article  Google Scholar 

  3. De Clercq, E., Biochem. Pharm., 2007, vol. 73, no. 7, p. 911. DOI: 10.1016/j.bcp.2006.09.014.

    Article  Google Scholar 

  4. Holy, A., Antiviral Res., 2006, vol. 71, no. 2–3, p. 248. DOI: 10.1016/j.antiviral.2006.06.002.

    Article  CAS  Google Scholar 

  5. De Clercq, E. and Holy, A., Antimicrob. Agents Chemother., 1991, vol. 35, no. 4, p. 701. DOI: 10.1128/AAC.35.4.701.

    Article  Google Scholar 

  6. Schutter, T.D., Andrei, G., Topalis, D., Duraffour, S., Mitera, T., Naesens, L., van den Oord, J., Matthys, P., and Snoeck, R., Cancer Lett., 2013, vol. 329, no. 2, p. 137. DOI: 10.1016/j.canlet. 2012.10.036.

    Article  Google Scholar 

  7. Starrett, J.E.Jr. and Tortolani, D.R., J. Med. Chem., 1994, vol. 37, no. 12, p. 1857. DOI: 10.1021/jm00038a015.

    Article  CAS  Google Scholar 

  8. Gerbig, U. and Balzarini, J., Antiviral Res., 2005, vol. 65, no. 3, p. A94. DOI: 10.1016/j.antiviral.2005.01.001.

    Google Scholar 

  9. Gosert, R., Rinaldo, C.H., Wernli, M., Major, E.O., and Hirsch, H.H., Antimicrob. Agents Chemother., 2011, vol. 55, no. 5, p. 2129. DOI: 10.1128/AAC.00046-11.

    Article  CAS  Google Scholar 

  10. Cesnek, M., Hockova, D., Holy, A., Dracinsky, M., Baszczynski, O., de Jersey, J., Keough, D.T., and Guddat, L.W., Bioorg. Med. Chem., 2012, vol. 20, no. 2, p. 1076. DOI: 10.1016/j.bmc.2011.11.034.

    Article  CAS  Google Scholar 

  11. Pradere, U., Garnier-Amblard, E.C., Coats, S.J., Amblard, F., and Schinazi, R.F., Chem. Rev., 2014, vol. 114, no. 18, p. 9154. DOI: 10.1021/cr5002035.

    Article  CAS  Google Scholar 

  12. Gable, J.E., Acker, T.M., and Craik, C.S., Chem. Rev., 2014, vol. 114, no. 22, p. 11382. DOI: 10.1021/cr500255e.

    Article  CAS  Google Scholar 

  13. Tichy, T., Andrei, G., Dracinsky, M., Holy, A., Balzarini, J., Snoeck, R., and Krecmerova, M., Bioorg. Med. Chem., 2011, vol. 19, no. 11, p. 3527. DOI: 10.1016/j.bmc.2011.04.016.

    Article  CAS  Google Scholar 

  14. Eriksson, U., Peterson, L.W., Kashemirov, B.A., Hilfinger, J.M., Drach, J.C., Borysko, K.Z., Breitenbach, J.M., Kim, J.S., Mitchell, S., Kijek, P., and McKenna, C.E., Mol. Pharmaceutics, 2008, vol. 5, no. 4, p. 598. DOI: 10.1021/mp8000099.

    Article  CAS  Google Scholar 

  15. Tollefson, A.E., Spencer, J.F., Ying, B., Buller, R.M.L., Wold, W.S.M., and Toth, K., Antiviral Res., 2014, vol. 112, p. 38. DOI: 10.1016/j.antiviral.2014.10.005.

    Article  CAS  Google Scholar 

  16. Ruiz, J., Beadle, J.R., Buller, R.M., Schreiwer, J., Prichard, M.N., Keith, K.A., Lewis, K.C., and Hostetler, K.Y., Bioorg. Med. Chem., 2011, vol. 19, no. 9, p. 2950. DOI: 10.1016/j.bmc. 2011.03.034.

    Article  CAS  Google Scholar 

  17. Beadle, J.R., Wan, W.B., Ciesla, S.L., Keith, K.A., Hartline, C., Kern, E.R., and Hostetler, K.Y., J. Med. Chem., 2006, vol. 49, no. 6, p. 2010. DOI: 10.1021/jm050473m.

    Article  CAS  Google Scholar 

  18. Hostetler, K.Y., Antiviral Res., 2009, vol. 82, no. 2, p. A84. DOI: 10.1016/j.antiviral.2009.01.005.

    Article  CAS  Google Scholar 

  19. Florescu, D.F. and Keek, M., Expert Review of Anti-Infective Therapy, 2014, vol. 12, no. 10, p. 1171. DOI: 10.1586/14787210.2014.948847.

    Article  CAS  Google Scholar 

  20. To, K.K.W., Chan, J.F.W., Tsang, A.K.L., Cheng, V.C.C., and Yuen, K.Y., Microbes and Infection, 2014. DOI: 10.1016/j.micinf. 2014.11.007.

    Google Scholar 

  21. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, no. 5, p. 3516. DOI: 10.1021/cr100264t.

    Article  CAS  Google Scholar 

  22. Lamoureaux, G. and Artavia, G., Curr. Med. Chem., 2010, vol. 17, no. 26, p. 2967. DOI: 10.2174/092986710792065027.

    Article  Google Scholar 

  23. Klimochkin, Yu., Baimuratov, M., Knyazeva, E., Baleeva, N., Leonova, M., Skomorokhov, M., Belanov, E., Balakhnin, S., Antiviral Res., 2011, vol. 90, no. 2, p. A71. DOI: 10.1016/j.antiviral.2011.03.150.

    Article  Google Scholar 

  24. Moiseev, I.K., Kon’kov, S.A., Ovchinnikov, K.A., Kilyaeva, N.M., Bormasheva, K.M., Nechaeva, O.N., Leonova, M.V., Klimochkin, Yu.N., Balakhnin, S.M., Bormotov, N.I., Serova, O.A., and Belanov, E.F., Pharm. Chem. J., 2012, vol. 45, no. 10, p. 588. DOI: 10.1007/s11094-012-0686-3.

    Article  CAS  Google Scholar 

  25. Klimochkin, Yu., Osyanin, V., Golovin, E., Leonova, M., Konkov, S., Kilyaeva, N., Bormotov, N., Serova, O., Balakhnin, S., and Belanov, E., Antiviral Res., 2010, vol. 86, no. 1, p. A59. DOI: 10.1016/j.antiviral.2010.02.447.

    Article  Google Scholar 

  26. Klimochkin, Yu., Osyanin, V., Krasnikov, P., Leonova, M., Golovin, E., Balackhnin, S., and Belanov, E., Antiviral Res., 2009, vol. 82, no. 2, p. A60. DOI: 10.1016/j.antiviral.2009.02.143.

    Google Scholar 

  27. Belanov, E., Leonova, M., Osyanin, V., Krasnikov, P., Kuznetsov, S., Shiryaev, A., Golovin, E., Serova, O., Bormotov, N., Balackhnin, S., and Klimochkin, Yu., Antiviral Res., 2009, vol. 82, no. 2, p. A32. DOI: 10.1016/j.antiviral.2009.02.060.

    Article  Google Scholar 

  28. Reznikov, A.N., Skomorokhov, M.Yu., and Klimochkin, Yu.N., Russ. J. Gen. Chem., 2012, vol. 82, no. 5, p. 835. DOI: 10.1134/S1070363212050052.

    Article  CAS  Google Scholar 

  29. Holy, A., Collect. Czech. Chem. Commun., 1979, vol. 44, no. 4, p. 1819. DOI: 10.1135/cccc19791819.

    Article  CAS  Google Scholar 

  30. Brodfuehrer, P.R., Howell, H.G., Sapino, Jr.C., and Vemishetti, P., Tetrahedron Lett., 1994, vol. 35, no. 20, p. 3243. DOI: 10.1016/S0040-4039(00)76875-4.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Samara State Technical University, ul. Molodogvardeiskaya 244, Samara, 443100, Russia

    A. N. Reznikov, M. Yu. Skomorokhov, M. V. Leonova & Yu. N. Klimochkin

Authors
  1. A. N. Reznikov
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  2. M. Yu. Skomorokhov
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  3. M. V. Leonova
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  4. Yu. N. Klimochkin
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Correspondence to A. N. Reznikov.

Additional information

Original Russian Text © A.N. Reznikov, M.Yu. Skomorokhov, M.V. Leonova, Yu.N. Klimochkin, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 2, pp. 229–235.

To the 80th Anniversary of B.I. Ionin

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Reznikov, A.N., Skomorokhov, M.Y., Leonova, M.V. et al. Synthesis of adamantyl-containing cidofovir analogs as potential antiviral prodrugs with high bioavailability parameters. Russ J Gen Chem 85, 402–408 (2015). https://doi.org/10.1134/S1070363215020097

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  • DOI: https://doi.org/10.1134/S1070363215020097

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