Skip to main content
SpringerLink
Log in

4-hydroxy-2-quinolones. 176*. 4-R-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. synthesis, physicochemical and biological properties

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

We have carried out the synthesis and a comparative analysis of the acidic properties of a large group of 4-R-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. Features of the recorded NMR spectra of these compounds are discussed together with their analgesic properties.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. I. V. Ukrainets, N. L. Bereznyakova, Liu Yangyang, and A. V. Turov, Khim. Geterotsikl. Soedin., 569 (2010). [Chem. Heterocycl. Comp., 46, 452 (2010)].

    Google Scholar 

  2. S. Jönsson, G. Andersson, T. Fex, T. Fristedt, G. Hedlund, K. Jansson, L. Abramo, I. Fritzson, O. Pekarski, A. Runström, H. Sandin, I. Thuvesson, and A. Björk, J. Med. Chem., 47, 2075 (2004).

    Article  Google Scholar 

  3. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, O. V. Shishkin, and A. V. Turov, Khim. Geterotsikl. Soedin., 1391 (2006). [Chem. Heterocycl. Comp., 42, 1208 (2006)].

    Google Scholar 

  4. J. H. M. Lange, P. C. Verveer, S. J. M. Osnabrug, and G. M. Visser, Tetrahedron Lett., 42, 1367 (2001).

    Article  CAS  Google Scholar 

  5. X. Collin, J. M. Robert, M. Duflos, G. Wielgosz, G. Le Baut, C. Robin-Dubigeon, N. Grimaud, F. Lang, and J. Y. Petit, J. Pharm. Pharmacol., 53, 417 (2001).

    Article  CAS  Google Scholar 

  6. A. Kutyrev and T. Kappe, J. Heterocycl. Chem., 34, 969 (1997).

    Article  CAS  Google Scholar 

  7. T. Kappe, C. Nuebling, K. Westphalen, U. Kardorff, W. Deyn, M. Gerber, and H. Walter, DE Pat. 4138820 (1993); http://ep.espacenet.com

  8. I. V. Ukrainets, P. A. Bezugly, S. G. Taran, O. V. Gorokhova, and A. V. Turov, Tetrahedron Lett., 36, 7747 (1995).

    Article  CAS  Google Scholar 

  9. M. Rowley, P. D. Leeson, G. I. Stevenson, A. M. Moseley, I. Stansfield, I. Sanderson, L. Robinson, R. Baker, J. A. Kemp, G. R. Marshall, A. C. Foster, S. Grimwood, M. D. Tricklebank, and K. L. Saywell, J. Med. Chem., 36, 3386 (1993).

    Article  CAS  Google Scholar 

  10. I. V. Ukrainets, O. L. Kamenetskaya, S. G. Taran, I. Yu. Petukhova, and L. N. Voronina, Khim. Geterotsikl. Soedin., 104 (2001). [Chem. Heterocycl. Comp., 37, 100 (2001)].

    Google Scholar 

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

    Google Scholar 

  12. R. T. Coutts and D. G. Wibberley, J. Chem. Soc., 2518 (1962).

  13. I. V. Ukrainets, S. G. Taran, O. V. Gorokhova, O. L. Kodolova, and A. V. Turov, Khim. Geterotsikl. Soedin., 928 (1997). [Chem. Heterocycl. Comp., 33, 811 (1997)].

    Google Scholar 

  14. I. V. Ukrainets, L. V. Sidorenko, S. V. Slobodzyan, V. B. Rybakov, and V. V. Chernyshev, Khim. Geterotsikl. Soedin., 1362 (2005). [Chem. Heterocycl. Comp., 41, 1158 (2005)].

    Google Scholar 

  15. I. V. Ukrainets, A. A. Tkach, E. V. Mospanova, and E. N. Svechnikova, Khim. Geterotsikl. Soedin., 1196 (2007). [Chem. Heterocycl. Comp., 43, 1014 (2007)].

    Google Scholar 

  16. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, S. V. Shishkina, and A. V. Turov, Khim. Geterotsikl. Soedin., 736 (2007). [Chem. Heterocycl. Comp., 43, 617 (2007)].

    Google Scholar 

  17. E. V. Kolesnik, Diss. Cand. Chem. Sci. [in Russian], Kharkiv (2009).

  18. I. V. Ukrainets, S. G. Taran, O. V. Gorokhova, N. A. Marusenko, S. N Kovalenko, A. V. Turov, N. I. Filimonova, and S. M. Ivkov, Khim. Geterotsikl. Soedin., 195 (1995). [Chem. Heterocycl. Comp., 31, 167 (1995)]

    Google Scholar 

  19. I. V. Ukrainets, P. A. Bezuglyi, Skaif Nikola, O. V. Gorokhova, and L. V. Sidorenko, Zh. Org. Farm. Khim., 2, No. 1, 39 (2004).

    CAS  Google Scholar 

  20. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 887 (2006). [Chem. Heterocycl. Comp., 42, 776 (2006)].

    Google Scholar 

  21. I. V. Ukrainets, O. V. Gorokhova, L. V. Sidorenko, and N. L. Bereznyakova, Khim. Geterotsikl. Soedin., 69 (2007). [Chem. Heterocycl. Comp., 43, 58 (2007)].

    Google Scholar 

  22. I. V. Ukrainets, N. L. Bereznyakova, V. A. Parshikov, and A. V. Turov, Khim. Geterotsikl. Soedin., 1496 (2007).[Chem. Heterocycl. Comp., 43, 1269 (2007)].

    Google Scholar 

  23. I. V. Ukrainets, N. L. Bereznyakova, V. A. Parshikov, and V. N. Kravchenko, Khim. Geterotsikl. Soedin., 78 (2008). [Chem. Heterocycl. Comp., 44, 64 (2008)].

    Google Scholar 

  24. S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, Abdel Naser Dakkah, and L. V. Sidorenko, Acta Crystallogr., E58, o254 (2002).

    CAS  Google Scholar 

  25. S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, and E. V. Kolesnik, Acta Crystallogr., E61, o1833 (2005).

    CAS  Google Scholar 

  26. M. D. Mashkovskii, Drugs, RIA Novaya volna: Umerenkov Publishing House, Moscow (2009), p. 162.

    Google Scholar 

  27. A. Albert and E. Sergeant, Ionization Constants of Acids and Bases [Russian translation], Khimiya, Moscow (1964).

    Google Scholar 

  28. E. N. L’vovskii, Statistical Methods of Deriving Empirical Formulae [in Russian], Moscow University (1988), p. 41.

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

    Google Scholar 

  30. B. Riegel, G. R. Lappin, B. H. Adelson, C. G. Albisetti, R. M. Dodson, and R. H. Baker, J. Am. Chem. Soc., 68, 1264 (1946).

    Article  CAS  Google Scholar 

  31. L. N. Sernov and V. V. Gatsura, Elements of Experimental Pharmacology [in Russian], Typography Nauka, Moscow (2000), p. 41.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National University of Pharmacy, Kharkiv, 61002, Ukraine

    I. V. Ukrainets, L. V. Sidorenko & E. N. Svechnikova

  2. N. I. Pirogov Vinitsa National Medical University, Vinnitsa, 21018, Ukraine

    A. A. Davidenko

  3. Chemical Technology Institute, V. Dal East-Ukrainian National University, Rubizhne, 93003, Ukraine

    E. V. Mospanova

Authors
  1. I. V. Ukrainets
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Davidenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Mospanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. V. Sidorenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. N. Svechnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Ukrainets.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 706-717, May, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ukrainets, I.V., Davidenko, A.A., Mospanova, E.V. et al. 4-hydroxy-2-quinolones. 176*. 4-R-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. synthesis, physicochemical and biological properties. Chem Heterocycl Comp 46, 559–568 (2010). https://doi.org/10.1007/s10593-010-0546-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0546-6

Keywords

Search

Navigation