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4-Hydroxy-2-quinolones. 38. Synthesis, structure, and anticonvulsant activity of optically active 1-phenylethylamides of 1-R-4-hydroxy-2-oxo-3-quinolinecarboxylic acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A synthesis is reported for optically pure antipodes of 1-phenylethylamides of 1-R-4-hydroxy-2-oxo-3-quinolinecarboxylic acids. An attempt was made to establish the absolute configuration of these products by X-ray diffraction crystallographic analysis. The anticonvulsant activity of the S-enantiomers was studied.

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References

  1. I. V. Ukrainets, S. G. Taran, L. V. Sidorenko, and O. V. Gorokhova,Khim. Geterotsikl. Soedin., No. 11, 1542 (1997).

    Google Scholar 

  2. R. Berkow and F. Fletcher (editors).Handbook of Medicine, Diagnostics and Therapy [Russian translation], Vol. 1, Mir, Moscow (1997), p. 979.

    Google Scholar 

  3. M. D. Mashkovskii,Medicinals [in Russian], vol. 1, Kharkov, Torsing (1997), p. 29.

    Google Scholar 

  4. I. V. Ukrainets, O. V. Gorokhova, S. G. Taran, P. A. Bezuglyi, and A. V. Turov,Khim. Geterotsikl. Soedin., No. 2, 229 (1994).

    Google Scholar 

  5. P. A. Bezuglyi, I. V. Ukrainets, V. A. Georgiyants, V. I. Treskach, N. G. Sergienko, V. N. Savchenko, and A. V. Turov,Farm. Zh., No. 6, 35 (1990).

    Google Scholar 

  6. I. V. Ukrainets, V. A. Georgiyants, N. G. Sergienko, and V. N. Savchenko,Farm. Zh., No. 4, part 2, 65 (1991).

    Google Scholar 

  7. V. M. Potapov,Stereochemistry [in Russian], Khimiya, Moscow (1988). p. 464.

    Google Scholar 

  8. G. Günther,Introduction to NMR Spectroscopy [Russian translation], Mir, Moscow (1984), p. 478.

    Google Scholar 

  9. I. V. Ukrainets, S. G. Taran, O. L. Kamenetskaya, O. V. Gorokhova, L. V. Sidorenko, and A. V. Turov,Khim. Geterotsikl. Soedin. (in press).

  10. P. Sykes,Reaction Mechanisms in Organic Chemistry [Russian translation], Khimiya, Moscow (1991). p. 447.

    Google Scholar 

  11. F. H. Allen and O. Kennard,Chem. Des. Autom. News, No. 8, 31 (1993).

    Google Scholar 

  12. H. Borowiec, J. Grochowski, and P. Serda,J. Chem. Res. Synop., No. 5, 248 (1996).

    Google Scholar 

  13. H. D. Flack,Acta Crystallogr.,A39, 876 (1983).

    Article  Google Scholar 

  14. H. D. Flack and D. Schwarzenbach,Acta Crystallogr.,A44, 499 (1988).

    Article  Google Scholar 

  15. V. V. Gatsura and A. S. Saratikov,Pharmacological Agents in Experimental Medicine and Biology [in Russian], Izd. Tomsk. Univ., Tomsk (1977), p. 155.

    Google Scholar 

  16. F. P. Vedyaev and T. M. Vorob'eva,Models and Mechanisms of Emotional Stress [in Russian], Zdorov'ya, Kiev (1983), p. 135.

    Google Scholar 

  17. Ya. Buresh, M. Petran', and D. Zakhar,Electrophysiological Research Methods [Russian translation]. Inostr. Lit., Moscow (1962), p. 466.

    Google Scholar 

  18. G. M. Sheldrick,SHELXS-97, Program for Solution of Crystal Structures, University of Göttingen, Germany (1997).

    Google Scholar 

  19. G. M. Sheldrick,SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).

    Google Scholar 

  20. A. L. Spek,PLUTON Molecular Graphics Program, University of Utrecht, The Netherlands (1997).

    Google Scholar 

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Authors and Affiliations

  1. Ukrainian Pharmaceutical Academy, 310002, Kharkov, Ukraine

    I. V. Ukrainets, S. G. Taran, N. V. Likhanova, O. V. Gorokhova & Nidal Amin Jaradat

  2. M. V. Lomonosov Moscow State University, 119899, Moscow, Russia

    V. B. Rybakov

Authors
  1. I. V. Ukrainets
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  2. S. G. Taran
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  3. N. V. Likhanova
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  4. V. B. Rybakov
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  5. O. V. Gorokhova
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  6. Nidal Amin Jaradat
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Additional information

For Communication 37, see ref. [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 55–63, January, 2000.

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Ukrainets, I.V., Taran, S.G., Likhanova, N.V. et al. 4-Hydroxy-2-quinolones. 38. Synthesis, structure, and anticonvulsant activity of optically active 1-phenylethylamides of 1-R-4-hydroxy-2-oxo-3-quinolinecarboxylic acids. Chem Heterocycl Compd 36, 49–56 (2000). https://doi.org/10.1007/BF02256844

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  • DOI: https://doi.org/10.1007/BF02256844

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