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2,1-Benzothiazine 2,2-Dioxides. 1. Synthesis, Structure, and Analgesic Activity of 1-R-4-Hydroxy-2,2-Dioxo-1H-2λ6,1-Benzothiazine-3-Carboxylic Acid Esters

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Chemistry of Heterocyclic Compounds Aims and scope

A preparative method for the synthesis of a series of 1-R-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylates has been developed. The special features of the steric structure for compounds of this class have been studied on the example of the 1-N-methyl derivative. Results of studying the analgesic properties of the substances obtained are given.

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References

  1. G. Kubin’i, Ros. Khim. J. (Zh. Russ. Khim. Obshchest. im D. I. Mendeleeva), L, No. 2, 5 (2006).

  2. J. P. Hughes, S. Rees, S. B. Kalindjian, and K. L. Philpott, Brit. J. Pharmacol., 162, 1239 (2011).

    Article  CAS  Google Scholar 

  3. I. V. Ukrainets, V. V. Kravtsova, A. A. Tkach, and V. B. Rybakov, Khim. Geterotsikl. Soedin., 875 (2009). [Chem. Heterocycl. Compd., 45, 698 (2009)].

    Google Scholar 

  4. I. V. Ukrainets, N. L. Bereznyakova, L. A. Grinevich, V. E. Kuz’min, and A. G. Artemenko, Khim. Geterotsikl. Soedin., 868 (2010). [Chem. Heterocycl. Compd., 46, 699 (2010)].

    Google Scholar 

  5. I. V. Ukrainets, A. A. Tkach. V. V. Kravtsova, V. I. Mamchur, and E. Yu. Kovalenko, Khim. Geterotsikl. Soedin., 1050 (2010). [Chem. Heterocycl. Compd., 46, 850 (2010)].

    Google Scholar 

  6. I. V. Ukrainets, L. A. Grinevich, A. A. Tkach, O. V. Gorokhova, V. N. Kravchenko, and G. Sim, Khim. Geterotsikl. Soedin., 1681 (2010). [Chem. Heterocycl. Compd., 46, 1364 (2010)].

    Google Scholar 

  7. I. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1690 (2010). [Chem. Heterocycl. Compd., 46, 1371 (2010)].

    Google Scholar 

  8. J. Minville, J. Poulin, C. Dufresne, and C. F. Sturino, Tetrahedron Lett., 49, 3677 (2008).

    Article  CAS  Google Scholar 

  9. K. Popov, T. Volovnenko, and J. Volovenko, Beilstein J. Org. Chem., 5, No. 42 (2009), DOI: 10.3762/bjoc.5.42.

  10. A. Fensome, J. Goldberg, C. C. McComas, E. J. Trybulski, R. P. Woodworth, D. C. Deecher. G. T. Whiteside, and P. Zhang, Bioorg. Med. Chem. Lett., 20, 1555 (2010).

    Google Scholar 

  11. M. Pieroni, S. Sabatini, S. Massari, G. W. Kaatz, V. Cecchetti, and O. Tabarrini, Med. Chem. Commun., 1092 (2012).

  12. I. V. Ukrainets, P. A. Bezuglyi, V. I. Treskach, A. V. Turov, and S. V. Slobodzyan, Khim. Geterotsikl. Soedin., 636 (1992). [Chem. Heterocycl. Compd., 28, 534 (1992)].

    Google Scholar 

  13. J. G. Lombardino and D. E. Kuhla, in: A. R. Katritzky and A. J. Boulton (editors), Advances in Heterocyclic Chemistry, Vol. 28, Academic Press, New York (1981), p. 73.

    Google Scholar 

  14. H. Becker, G. Domschke, E. Fanghenel, M. Fisher, K. Gevald, R. Maier, D. Pafel, G. Schmidt, K. Shvetlik, V. Berger, I. Faust, F. Gents, R. Gluh, K. Muller, K. Schollberg, E. Zailer, and G. Zeppenfeld, Organikum [Russian translation], Vol. 2, Mir, Moscow (1992), p. 295.

  15. I. V. Ukrainets, Diss. Dr. Sci. Chem, Kharkov (1992).

  16. I. V. Ukrainets, L. V. Sidorenko, L. A. Petrushova, and O. V. Gorokhova, Khim. Geterotsikl. Soedin., 71 (2006). [Chem. Heterocycl. Compd., 42, 64 (2006)].

    Google Scholar 

  17. N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya, J. Phys. Org. Chem., 3, 147 (1990).

    Article  CAS  Google Scholar 

  18. S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, and L. V. Sidorenko, Acta Crystallogr., E61, o4180 (2005).

    Google Scholar 

  19. I. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1690 (2010). [Chem. Heterocycl. Compd., 46, 1371 (2010)].

    Google Scholar 

  20. I. V. Ukrainets, E. V. Mospanova, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1287 (2012). [Chem. Heterocycl. Compd., 48, 1200 (2012)].

    Google Scholar 

  21. H.-B. Burgi and J. D. Dunitz, Structure Correlation, Vol. 2, VCH, Weinheim (1994), p. 741.

  22. Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).

    CAS  Google Scholar 

  23. H. G. Vogel (editor), Drug Discovery and Evaluation: Pharmacological Assays, 3rd edition, Springer, Berlin (2008), p. 1011.

  24. B. Loev and K. M. Snader, J. Heterocycl. Chem., 4, 403 (1967).

    Article  CAS  Google Scholar 

  25. M. Shafiq, M. Zia-ur-Rehman, I. U. Khan, M. N. Arshad, and S. A. Khan, J. Chil. Chem. Soc., 56, 527 (2011).

    Article  CAS  Google Scholar 

  26. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

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Authors and Affiliations

  1. National University of Pharmacy, 53 Pushkinska St., Kharkiv, 61002, Ukraine

    I. V. Ukrainets & L. A. Petrushova

  2. Vinnitsa N. I. Pirogov National Medicinal University, 56 Pirogova St., Vinnitsa, 21018, Ukraine

    S. P. Dzyubenko

Authors
  1. I. V. Ukrainets
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  2. L. A. Petrushova
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  3. S. P. Dzyubenko
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Correspondence to I. V. Ukrainets.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1479-1485, September, 2013.

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Ukrainets, I.V., Petrushova, L.A. & Dzyubenko, S.P. 2,1-Benzothiazine 2,2-Dioxides. 1. Synthesis, Structure, and Analgesic Activity of 1-R-4-Hydroxy-2,2-Dioxo-1H-2λ6,1-Benzothiazine-3-Carboxylic Acid Esters. Chem Heterocycl Comp 49, 1378–1383 (2013). https://doi.org/10.1007/s10593-013-1388-9

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  • DOI: https://doi.org/10.1007/s10593-013-1388-9

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