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Synthesis and chemical properties of adamantylated nucleic bases and related compounds

  • Drug Synthesis Methods and Manufacturing Technology
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Pharmaceutical Chemistry Journal Aims and scope

Data published in 1999 – 2011 on the synthesis and chemical properties of adamantyl-containing nucleic bases and related compounds are reviewed, systematized, and analyzed. Adamantyl-containing heterocyclic compounds, which have received much attention in attempts to create highly effective and selective drugs that were described in previous reviews devoted to heteryladamantanes, occupy a special place in adamantane chemistry. The number of publications devoted to the synthesis and characterization of adamantyl-containing nucleic bases was small and restricted mostly to derivatives containing unsubstituted adamantane. The ability to overcome this limitation was realized only in the last decade. Available data on the biological activity of synthesized compounds indicate good prospects for research in this direction.

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References

  1. M.-G. A. Shvekhgeimer, Usp. Khim., 65(7), 603–647 (1996).

    CAS  Google Scholar 

  2. V. P. Litvinov and M.-G. A. Shvekhgeimer, Zh. Org. Khim., 33(10), 1447–1471 (1997).

    Google Scholar 

  3. M.-G. A. Shvekhgeimer and V. P. Litvinov, Zh. Org. Khim., 35(2), 183–220 (1999).

    Google Scholar 

  4. M.-G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., No. 4, 435–482 (1997).

  5. V. P. Litvinov, Khim. Geterotsikl. Soedin., No. 1, 12–39 (2002).

  6. J. Balzarini, B. Orzeszko-Krzesinska, J. K. Maurin, and A. Orzeszko, Eur. J. Med. Chem., 44(1), 303–311 (2009).

    CAS  PubMed  Google Scholar 

  7. B. Orzeszko, M. Fedorynski, A. E. Laudy, et al., Acta Pol. Pharm., 63(5), 374–377 (2006).

    CAS  PubMed  Google Scholar 

  8. J. Gao, R. F. Henry, T. G. Pagano, et al., Tetrahedron Lett., 48(41), 7395–7398 (2007).

    CAS  Google Scholar 

  9. N. V. Makarova, M. N. Zemtsova, and I. K. Moiseev, Khim. Geterotsikl. Soedin., No. 7, 912–915 (2001).

  10. N. V. Makarova, M. N. Zemtsova, and I. K. Moiseev, Khim. Geterotsikl. Soedin., No. 5, 709–711 (2003).

  11. N. V. Makarova, E. I. Boreko, I. K. Moiseev, et al., Khim-farm. Zh., 36(1), 5–7 (2002).

    Google Scholar 

  12. I. A. Novakov, B. S. Orlinson, and M. B. Navrotskii, Zh. Org. Khim., 45(2), 325–326 (2009).

    Google Scholar 

  13. N. Kolocouris, G. Zoidis, G. B. Foscolos, et al., Bioorg. Med. Chem. Lett., 17(15), 4358–4362 (2007).

    CAS  PubMed  Google Scholar 

  14. B. Orzeszko, A. E. Laudy, B. J. Starosciak, et al., Acta Pol. Pharm. Drug Res., 61(6), 455–460 (2004).

    CAS  Google Scholar 

  15. B. Orzeszko, Z. Kazimierczuk, J. K. Maurin, et al., Il Farmaco, 59(12), 929–937 (2004).

    CAS  PubMed  Google Scholar 

  16. V. Kovalev, E. Shokova, A. Shmailov, et al., Eur. J. Org. Chem., 19, 3754–3761 (2010).

    Google Scholar 

  17. E. A. Shokova and V. V. Kovalev, Usp. Khim., 80(10), 971–995 (2011).

    Google Scholar 

  18. V. V. Kovalev, E. A. Shokova, and A. K. Rozov, RU Pat. No. 2,064,930 (1996); Byull. Izobret., No. 96 (1996).

  19. V. V. Kovalev, A. N. Khomich, E. A. Shokova, and Yu. N. Luzikov, New J. Chem., 20(4), 483–492 (1996).

    CAS  Google Scholar 

  20. E. A. Shokova, A. E. Motornaya, A. K. Shestakova, and V. V. Kovalev, Tetrahedron Lett., 45(4), 6465–6469 (2004).

    CAS  Google Scholar 

  21. E. Erochina, E. Shokova, Yu. Luzikov, and V. Kovalev, Synthesis, 7, 851–854 (1995).

    Google Scholar 

  22. V. V. Kovalev, O. A. Fedorova, and E. A. Shokova, Zh. Org. Khim,, 23(9), 1882–1886 (1987).

    CAS  Google Scholar 

  23. E. Shokova, V. Tafeenko, and V. Kovalev, Tetrahedron Lett., 43(29), 5153–5156 (2002).

    CAS  Google Scholar 

  24. E. A. Shokova, E. V. Khomich, N. N. Akhmetov, et al., Zh. Org. Khim., 39(3), 400–414 (2003).

    Google Scholar 

  25. E. A. Shokova, L. M. Alimbarova, and V. V. Kovalev, Khim.-farm. Zh., 33(7), 30–33 (1999).

    Google Scholar 

  26. V. V. Kovalev, E. A. Shokova, and A. K. Rozov, Tetrahedron, 52(11), 3983–3990 (1996).

    CAS  Google Scholar 

  27. E. Shokova, T. Mousoulou, Yu. Luzikov, and V. Kovalev, Synthesis, 9, 1034–1040 (1997).

    Google Scholar 

  28. E. A. Shokova, T. Mousoulou, Yu. N. Luzikov, and V. V. Kovalev, Zh. Org. Khim., 35(6), 869–881 (1999).

    Google Scholar 

  29. Z. Kazimierczuk and A. Orzeszko, Helv. Chim. Acta., 82(11), 2020–2027 (1999).

    CAS  Google Scholar 

  30. J. K. Maurin, W. Lasek, A. Gorska, et al., Chem. Biodiversity, 1(10), 1498–1512 (2004).

    CAS  Google Scholar 

  31. J. K. Maurin, W. Lasek, A. Gorska, et al., Anti-Cancer Drug Des., 16(2), 73–80 (2001).

    CAS  Google Scholar 

  32. A. Shmailov, L. Alimbarova, E. Shokova, et al., Tetrahedron, 66(16), 3058–3064 (2010).

    CAS  Google Scholar 

  33. S. Prachayasittikul, A. Worachartcheewan, C. Nantasenamat, et al., Eur. J. Med. Chem., 46(2), 738–742 (2011).

    CAS  PubMed  Google Scholar 

  34. S. Prachayasittikul, N. Sornsongkhram, R. Pingaew, et al., Eur. J. Sci. Res., 36(2), 236–245 (2009).

    Google Scholar 

  35. B. Orzeszko, T. Switaj, A. B. Jakubowska-Mucka, et al., Z. Naturforsch. B: Chem. Sci., 60(4), 471–475 (2005).

    CAS  Google Scholar 

  36. A. I. Rakhimov and E. S. Titova, Zh. Org. Khim., 43(10), 92–98 (2007).

    Google Scholar 

  37. D. Pappo, S. Shimony, and Y. Kashman, J. Org. Chem., 70(1), 199–205 (2005).

    CAS  PubMed  Google Scholar 

  38. D. C. Martyn, A. Nijjar, C. A. Celatka, et al., Bioorg. Med. Chem. Lett., 20(1), 228–231 (2010).

    CAS  PubMed  Google Scholar 

  39. A. P. Thomas and T. Nowak, PCT Int. Appl. WO 2006106307 (2006).

    Google Scholar 

  40. I. A. Novakov, B. S. Orlinson, R. V. Brunilin, et al., Khim. Geterotsikl. Soedin., 37(10), 1541–1544 (2006).

    Google Scholar 

  41. I. A. Novakov, B. S. Orlinson, and M. B. Navrotskii, RU Pat. No. 2,238,269; Byull. Izobret., No. 29 (2004).

  42. A. Drabczynska, O. Yuzlenko, M. Kose, et al., Eur. J. Med. Chem., 46(9), 3590–3607 (2011).

    CAS  PubMed  Google Scholar 

  43. J. I. Bardagi and R. A. Rossi, J. Org. Chem., 75(15), 5271–5277 (2010).

    CAS  PubMed  Google Scholar 

  44. M. Rouchal, M. Necas, and R. Vicha, Acta Crystallogr. Sect. E: Struct. Rep. Online, 65, 1268 (2009).

    Google Scholar 

  45. G. Pastorin, C. Bolcato, B. Cacciari, et al., Il Farmaco, 60(4), 299–306 (2005).

    CAS  PubMed  Google Scholar 

  46. G. Pastorin, C. Bolcato, B. Cacciari, et al., Il Farmaco, 60(8), 643–651 (2005).

    CAS  PubMed  Google Scholar 

  47. K. Petersson, B. T. Pedersen, D. Staerk, et al., Eur. J. Pharm. Sci., 23, 337–345 (2004).

    CAS  PubMed  Google Scholar 

  48. K. L. Dueholm, M. Egholm, C. Behrens, et al., J. Org. Chem., 59(19), 5767–5773 (1994).

    CAS  Google Scholar 

  49. A. Maciollek, M. Munteanu, and H. Ritter, Macromol. Chem. Rev., 211(2), 245–249 (2010).

    CAS  Google Scholar 

  50. A. Gyrska, M. Andrzejewska, J. Kaminski, and Z. Kazimierczuk, Nucleosides, Nucleotides Nucleic Acids, 22(1), 13–19 (2003).

    Google Scholar 

  51. M. V. Skorobogatyi, A. V. Ustinov, I. A. Stepanova, et al., Org. Biomol. Chem., 4(6), 1091–1096 (2006).

    CAS  PubMed  Google Scholar 

  52. X.-H. Yang, S. Singh, J. Diakur, and L. I. Wiebe, J. Pharm. Pharm. Sci., 11(2), 32s–43s (2008).

    CAS  PubMed  Google Scholar 

  53. P. G. Baraldi, F. Fruttarolo, M. A. Tabrizi, et al., J. Med. Chem., 47(22), 5535–5540 (2004).

    CAS  PubMed  Google Scholar 

  54. D. K. Tosh, M. Chinn, L. S. Yoo, et al., Bioorg. Med. Chem., 18(2), 508–517 (2010).

    CAS  PubMed  Google Scholar 

  55. R. Chinchilla and C. Najera, Chem. Rev., 107(3), 874–922 (2007).

    CAS  PubMed  Google Scholar 

  56. T. E. Tyobeka, R. A. Hancock, and H. Weigel, Tetrahedron, 44(7), 1971–1978 (1988).

    CAS  Google Scholar 

  57. S. F. Zakrzewski and E. A. Evans, J. Labelled Compd. Radiopharm., 18(5), 683–693 (1981).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Moscow State University, Moscow, Russia

    E. A. Shokova & V. V. Kovalev

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  1. E. A. Shokova
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  2. V. V. Kovalev
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 47, No. 5, pp. 32 – 48, May, 2013.

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Shokova, E.A., Kovalev, V.V. Synthesis and chemical properties of adamantylated nucleic bases and related compounds. Pharm Chem J 47, 264–280 (2013). https://doi.org/10.1007/s11094-013-0942-1

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  • DOI: https://doi.org/10.1007/s11094-013-0942-1

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