Skip to main content
Log in

4-hydroxy-2-quinolones. 202*. Synthesis, chemical and biological properties of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In continuation of the search for potential analgesics amongst 4-hydroxyquinol-2-one derivatives we have proposed and carried out a preparative method of synthesis of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides. It has been shown that bromination of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid allylamide using an equivalent of molecular bromine occurs with a conventional addition of the halogen to the allyl double bond and not with halocyclization. The results of the study of the analgesic properties of the compounds prepared are presented.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. Ukrainets, N. Yu. Golik, A. L. Shemchuk, and V. N. Kravchenko, Khim. Geterotsikl. Soedin., 1364 (2011). [Chem. Heterocycl. Compd., 47, 1122 (2011)].

    Google Scholar 

  2. Rundshagen, Anästhesiol. Intensivmed. Notfallmed. Schmerzther, 45, 304 (2010).

  3. D. Rainsford, W. F. Kean, and G. E. Ehrlich, Curr. Med. Res. Opin., 24, 2967 (2008).

    Article  CAS  Google Scholar 

  4. G. McCleane, Anesthesiol. Clin., 25, 825 (2007).

    Article  CAS  Google Scholar 

  5. A. Kleeman and J. Engel, Pharmaceutical Substances. Synthesis, Patents, and Applications, Georg Thieme Verlag, Stuttgart (2001).

    Google Scholar 

  6. M. D. Mashkovskii, Drugs [in Russian], RIA Novaya Volna, Moscow (2009), p. 143.

    Google Scholar 

  7. R. S. Sinatra, J. S. Jahr, and J. M. Watkins-Pitchford (editors), The Essence of Analgesia and Analgesics, Cambridge University Press, Cambridge (2010).

    Google Scholar 

  8. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, and S. V. Shishkina, Khim. Geterotsikl. Soedin., 1345 (2010). [Chem. Heterocycl. Compd., 46, 1084 (2010)].

    Google Scholar 

  9. 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 

  10. V. Ukrainets, L. V. Sidorenko, E. N. Svechnikova, and O. V. Shishkin, Khim. Geterotsikl. Soedin., 1503 (2007). [Chem. Heterocycl. Compd., 43, 1275 (2007)].

    Google Scholar 

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

    Google Scholar 

  12. V. Ukrainets, N. L. Bereznyakova, O. V. Gorokhova, and A. V. Turov, Khim. Geterotsikl. Soedin., 1677 (2007). [Chem. Heterocycl. Compd., 43, 1426 (2007)].

    Google Scholar 

  13. M. A. Mokhort, L. V. Yakovleva, and O. M. Shapoval in: O. V. Stefanov (editor), Preclinical Investigation of Medicinal Agents: Methodological Recommendation [in Ukrainian], Avitsena, Kyiv (2001), p. 307.

    Google Scholar 

  14. N. Sernov and V. V. Gatsura, Elements of Experimental Pharmacology [in Russian], PPP Tipografiya "Nauka", Moscow (2000), p. 40.

    Google Scholar 

  15. V. Ukrainets, E. V. Mospanova, L. V. Savchenkova, and S. I. Yankovich, Khim. Geterotsikl. Soedin., 90 (2011). [Chem. Heterocycl. Compd., 47, 67 (2011).

    Google Scholar 

  16. Ya. A. Sigidin, G. Ya. Shvarts, A. P. Arzamastsev, and S. S. Liberman, Drug Therapy of the Anti- inflammatory Process (Experimental and Clinical Pharmacology of Anti-inflammatory Medications), Meditsina, Moscow (1988), p. 62.

  17. V. Ukrainets, A. A. Davidenko, E. V. Mospanova, L. V. Sidorenko, and E. N. Svechnikova, Khim. Geterotsikl. Soedin., 706 (2010). [Chem. Heterocycl. Compd., 46, 559 (2010).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. V. Ukrainets.

Additional information

*For Communication 201, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 339-346, February, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ukrainets, I.V., Bevz, O.V., Mospanova, E.V. et al. 4-hydroxy-2-quinolones. 202*. Synthesis, chemical and biological properties of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides. Chem Heterocycl Comp 48, 320–326 (2012). https://doi.org/10.1007/s10593-012-0992-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-0992-4

Keywords

Navigation