Advertisement

Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1084–1095 | Cite as

4-Hydroxy-2-quinolones. 180*. Synthesis, chemical reactions, and analgesic activity of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides

  • I. V. UkrainetsEmail author
  • E. V. Mospanova
  • A. A. Davidenko
  • S. V. Shishkina
Article

A targeted synthesis was carried out of a series of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-di-hydroquinoline-3-carboxylic acid alkylamides which show interest for biological study as potential analgesics. It was found that, in the presence of one equivalent of bromine, the compounds indicated undergo halocyclization to the corresponding 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxa-zolo[3,2-a]quinoline-4-carboxylic acid alkylamides. However, with an excess of bromine the reaction occurs somewhat differently and concludes with the formation of complexes of bromine with 4-alkyl-carbamoyl-2-bromomethyl-5-hydroxy-7,8-dimethoxy-1,2-dihydrooxazolo[3,2-a]quinolinium ditri- bromides. According to the results of pharmacological screening there are found compounds within the substances discovered with high analgesic activity.

Keywords

4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides analgesic activity amidation bromination halocyclization X-ray structural analysis 

References

  1. 1.
    I. V. Ukrainets, E. V. Mospanova, A. A. Davidenko, A. A. Tkach, and O. V. Gorokhova, Khim. Geterotsikl. Soedin., 1173 (2010). [Chem. Heterocycl. Comp., 46, 947 (2010)].Google Scholar
  2. 2.
    I. V. Ukrainets, L. V. Sidorenko, A. A. Davidenko, and A. K. Yarosh, Khim. Geterotsikl. Soedin., 560 (2010). [Chem. Heterocycl. Comp., 46, 445 (2010)].Google Scholar
  3. 3.
    I. V. Ukrainets, A. A. Davidenko, E. V. Mospanova, L. V. Sidorenko, and E. N. Svechnikova, Khim. Geterotsikl. Soedin., 706 (2010). [Chem. Heterocycl. Comp., 46, 559 (2010)].Google Scholar
  4. 4.
    I. V. Ukrainets, N. L. Bereznyakova, and E. V. Mospanova, Khim. Geterotsikl. Soedin., 1015 (2007). [Chem. Heterocycl. Comp., 43, 856 (2007)].Google Scholar
  5. 5.
    S. V. Shishkina, O. V. Shishkin, I. V. Ukrainets, N. L. Bereznyakova, and A. A. Davidenko, Acta Crystallogr., E64, o1031 (2008).Google Scholar
  6. 6.
    Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).Google Scholar
  7. 7.
    H.-B. Burgi and J. D. Dunitz, Structure Correlation, Vol. 2, VCH, Weinheim (1994), p. 741.Google Scholar
  8. 8.
    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
  9. 9.
    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
  10. 10.
    L. N. Sernov and V. V. Gatsura, Elements of Experimental Pharmacology [in Russian], Tipografiya “Nauka”, Moscow (2000), p. 41.Google Scholar
  11. 11.
    M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Umerenkov Publishing House, Moscow (2009), p. 162.Google Scholar
  12. 12.
    A. Kleemann and J. Engel, Pharmaceutical Substances. Synthesis, Patents, Applications, Multimedia Viewer, Version 2.00. Georg Thieme Verlag, Stuttgart (2001).Google Scholar
  13. 13.
    G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data. Rev. 5.1 (1998).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • I. V. Ukrainets
    • 1
    Email author
  • E. V. Mospanova
    • 2
  • A. A. Davidenko
    • 3
  • S. V. Shishkina
    • 4
  1. 1.National University of PharmacyKharkivUkraine
  2. 2.Chemical Technology InstituteV. Dal East-Ukrainian National UniversityRubizhneUkraine
  3. 3.N. I. Pirogov National Medical UniversityVinnitsaUkraine
  4. 4.Institute for Single CrystalNational Academy of Sciences of UkraineKharkivUkraine

Personalised recommendations