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2-Allyloxy/propargyloxypyridines: synthesis, structure, and biological activity

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Abstract

The alkylation (allylation and propargylation) of 3-cyano-6-dialkylamino-2-pyridones containing a d-annulated ring occurs at the oxygen atom. The structures of the starting compounds and their alkylation products were determined by X-ray diffraction. The neurotropic and antimicrobial activity of alkylation products was examined.

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References

  1. T. Shimatani, M. Inoue, T. Kuroiwa, J. Xu, M. Nakamura, S. Tazuma, K. Ikawa, N. Morikawa, Dig. Dis. Sci., 2006, 51, 114.

    Article  CAS  Google Scholar 

  2. G. Gariraghi, S. Banfi, U. Cornelli, M. Pinzaand G. Pifferi, Farmaco Sci., 1977, 32, 286.

    Google Scholar 

  3. D. G. McDevitt, Eur. Heart J., 1987, 8, 9.

    Article  CAS  Google Scholar 

  4. K. Yoshioka, H. Nakashita, D. F. Klessig, I. Yamaguchi, Plant J., 2001, 25, 149.

    Article  CAS  Google Scholar 

  5. A. Pedrazzoli, L. Dall´asta, G. Maffi, A. Giudice, E. Ferrero, Boll. Chim. Farm., 1976, 115, 125.

    CAS  Google Scholar 

  6. N. S. Radin, Drug Dev. Res., 2008, 69, 15.

    Article  CAS  Google Scholar 

  7. V. B. Rybakov, A. A. Bush, E. V. Babaev, L. A. Aslanov, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2004, 60, o160.

    Article  CAS  Google Scholar 

  8. O. S. Mazina, V. B. Rybakov, V. V. Chernyshev, E. V. Babaev, L. A. Aslanov, Crystallogr. Rep., 2004, 49, 998.

    Article  CAS  Google Scholar 

  9. O. S. Mazina, V. B. Rybakov, S. I. Troyanov, E. V. Babaev, L. A. Aslanov, Crystallogr. Rep., 2005, 50, 61.

    Article  CAS  Google Scholar 

  10. V. B. Rybakov, E. V. Babaev, Chem. Heterocycl. Compd., 2014, 50, 225.

    Article  CAS  Google Scholar 

  11. E. V. Babaev, O. S. Mazina, V. B. Rybakov, Stroenie tritsik-lov na osnove nitrilov tsikloalkanopiridinov [Structures of Tri-cyclic Compounds Based on Cycloalkanopyridine Nitriles], Lambert Acad. Publ., Saarbrucken, 2016, 188 pp. (in Russian).

    Google Scholar 

  12. V. B. Rybakov, E. V. Babaev, E. G. Paronikyan, Crystallogr. Rep., 2017, 62, 219.

    Article  CAS  Google Scholar 

  13. D. V. Albov, E. I. Turubanova, V. B. Rybakov, E. V. Ba-baev, L. A. Aslanov, Acta Crystallogr., Sect. E: Struct. Rep. Online, 2004, 60, o1222.

    Article  CAS  Google Scholar 

  14. E. G. Paronikyan, A. S. Noravyan, Sh. Sh. Dashyan, R. A. Tamazyan, A. G. Aivazyan, G. A. Panosyan, Chem. Hetero-cycl. Compd., 2013, 49, 1151.

    Article  CAS  Google Scholar 

  15. S. R. LaPlante, F. Bilodeau, N. Aubry, J. R. Gillard, J. O´Meara, R. Coulombe, Bioorg. Med. Chem. Lett., 2013, 23, 4663.

    Article  CAS  Google Scholar 

  16. H. Meislich, in Pyridine and its Derivatives, Part III, Ed. E. Klingsberg, Intersci. Publ., New York, 1962, p. 511.

  17. P. A. Keller, in Science of Synthesis, Ed. M. Priyaa, Thieme, Stuttgart, 2005, Vol. 15, p. 285.

    Google Scholar 

  18. D. V. Albov, V. B. Rybakov, E. V. Babaev, L. A. Aslanov, Crystallogr. Rep., 2004, 49, 430.

    Article  CAS  Google Scholar 

  19. E. V. Babaev, D. V. Albov, V. B. Rybakov, Struktura tsik-loalkanopiridonov i produktov ikh geterotsiklizatsii [Structures of Cycloalkanopyridines and Their Heterocyclization Prod-ucts], Lambert Acad. Publ., Saarbrucken, 2016, 180 pp. (in Russian).

    Google Scholar 

  20. B. Os´mia owski, E. Kolehmainen, S. Ikonen, K. Ahonen, M. Löfman, J. Mol. Struct., 2011, 1006, 678.

    Article  Google Scholar 

  21. P. J. Turrell, A. D. Hill, S. K. Ibrahim, J. A. Wright, C. J. Pickett, Dalton Trans., 2013, 42, 8140.

    Article  CAS  Google Scholar 

  22. H. G. Vogel, W. H. Vogel, in Drug Discovery and Evalua-tion: Pharmacological Assays, Ed. H. G. Vogel, Springer, Berlin–New York, 2008, p. 569.

  23. W. Loscher, D. Schmidt, Epilepsy Res., 1988, 2, 145.

    Article  CAS  Google Scholar 

  24. E. A. Swinyard, in Experimental Models of Epilepsy, Raven Press, New York, 1992, p. 433.

    Google Scholar 

  25. K. A. Gevorkyan, G. L. Papayan, S. G. Chshmarityan, R. G. Paronikyan, N. E. Akopyan, A. P. Engoyan, Pharm. Chem. J., 1987, 21, 95.

    Article  Google Scholar 

  26. Drugs Used in Generalized Seizures. Basic and Clinical Phar-macology, 9th ed., Ed. B. Katzung, Large Medical Books, McGraw-Hill, 2003.

    Google Scholar 

  27. N. W. Dunham, T. S. Miya, J. Am. Pharm. Ass. Sci. Ed., 1957, 46, 208.

    Article  CAS  Google Scholar 

  28. B. J. Jones, D. J. Roberts, J. Pharm. Pharmacol., 1968, 20, 302.

    Article  CAS  Google Scholar 

  29. M. L. Belen´kii, Elementy kolichestvennoi otsenki farmako-logicheskogo effekta [Elements of Quantitative Evaluation of the Pharmacological Effect], Meditsina, Leningrad, 1961, 152 pp. (in Russian).

    Google Scholar 

  30. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv [Manual for Preclinical Studies of Drugs], Ed. A. N. Mironov, Meditsina, Moscow, 2012, Part. 1, p. 509 (in Russian).

    Google Scholar 

  31. Lekarstvennye sredstva [Drugs], 16th ed., Ed. M. D. Mash-kovskii, Novaya Volna, Moscow, 2010, p. 851 (in Russian).

    Google Scholar 

  32. X-ARIA, X-RED, Stoe & Cie, Darmstadt, 2015.

  33. N. Walker, D. Stuart, Acta Crystallogr., Sect. A: Found. Crys-tallogr., 1983, 39, 158.

    Article  Google Scholar 

  34. G. M. Sheldrick, Acta Crystallogr., Sect. D: Biol. Crystal-logr., 2010, 66, 479.

    Article  CAS  Google Scholar 

  35. T. Gruene, H. W. Hahn, A. V. Luebben, F. Meilleur, G. M. Sheldrick, J. Appl. Crystallogr., 2014, 47, 462.

    Article  CAS  Google Scholar 

  36. A. L. Spek, Acta Crystallogr., Sect. D: Biol. Crystallogr., 2009, 65, 148.

    Article  CAS  Google Scholar 

  37. C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr., Sect. B: Struct. Sci., Cryst. Eng. Mater., 2016, 72, 171.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1, Build. 3, Leninskie Gory, 119992, Moscow, Russian Federation

    E. V. Babaev, Y. I. Koval, V. B. Rybakov, S. A. Rzhevskii & I. A. Shadrin

  2. A. L. Mnjoyan Institute of Fine Organic Chemistry of Scientific-Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan aven., 0014, Yerevan 26, Armenia

    E. G. Paronikyan, G. M. Stepanyan, R. G. Paronikyan & Sh. Sh. Dashyan

Authors
  1. E. V. Babaev
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  2. Y. I. Koval
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  3. V. B. Rybakov
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  4. E. G. Paronikyan
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  5. G. M. Stepanyan
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  6. R. G. Paronikyan
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  7. Sh. Sh. Dashyan
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  8. S. A. Rzhevskii
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  9. I. A. Shadrin
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Correspondence to Y. I. Koval.

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Babaev, E.V., Koval, Y.I., Rybakov, V.B. et al. 2-Allyloxy/propargyloxypyridines: synthesis, structure, and biological activity. Russ Chem Bull 67, 313–320 (2018). https://doi.org/10.1007/s11172-018-2076-9

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  • DOI: https://doi.org/10.1007/s11172-018-2076-9

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