Synthesis and biological activity of substituted 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides

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Abstract

A four-component solvent-free reaction of acetoacetic acid amide with dimedone, aromatic aldehydes and ammonium acetate leads to new substituted 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides. The structures of the products were proved using IR, 1H and 13C NMR spectroscopy, mass spectrometry and X-ray diffraction analysis. The synthesized compounds were tested for antimicrobial and antinociceptive activities.

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About the authors

N. V. Nosova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Author for correspondence.
Email: geinvl48@mail.ru
ORCID iD: 0000-0001-6380-2543
Russian Federation, Perm

М. О. Starovoytova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
Russian Federation, Perm

R. R. Mahmudov

Perm State National Research University; Federal Scientific Center for Medical and Preventive Health Risk Management Technologies

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-2326-3976
Russian Federation, Perm; Perm

V. V. Novikova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
Russian Federation, Perm

М. V. Dmitriev

Perm State National Research University

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, Perm

V. L. Gein

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: geinvl48@mail.ru
ORCID iD: 0000-0002-8512-0399
Russian Federation, Perm

References

  1. Ajani O.O., Iyaye K.T., Ademosun O.T. // RSC Adv. 2022. Vol. 12. P. 18594. doi: 10.1039/d2ra02896d
  2. Машковский М.Д. Лекарственные средства. M.: Новая волна, 2005. 1200 с.
  3. Scott D.A., Balliet C.L., Cook D.J., Davies A.M., Gero T.W., Omer C.A., Poondru S., Theoclitou M.E., Tyurin B., Zinda M.J. // Bioorg. Med. Chem. Lett. 2009. Vol. 19. P. 697. doi: 10.1016/j.bmcl.2008.12.046
  4. Chen S., Chen R., He M., Pang R., Tan Z., Yang M. // Bioorg. Med. Chem. 2009. Vol. 17. P. 1948. doi 10.1016/ j.bmc.2009.01.038
  5. Vanaerschot M., Lucantoni L., Li T., Combrinck J.M., Ruecker A., Santha T.R.K., Rubiano K., Ferreira E.P., Siciliano G., Gulati S., Henrich P.P., Ng L.C., Murithi J.M., Corey V.C., Duffy S., Lieberman O.J., Veiga M.I., Sinden R.E., Alano P., Delves M.J., Sim K.L, Winzeler E.A., Egan T.J., Hoffman S.L., Avery V.M., Fidock D.A. // Nat. Microbiol. 2017. Vol. 2. P. 1403. doi: 10.1038/s41564-017-0007-4
  6. Alqasoumi S.I., Al-Taweel A.M., Alafeefy A.M., Hamed M.M., Noaman E., Ghorab M.M. // Bioorg. Med. Chem. Lett. 2009. Vol. 19. P. 6939. doi 10.1016/ j.bmcl.2009.10.065
  7. Shahraki O., Edraki N., Khoshneviszadeh M., Zargari F., Ranjbar S., Saso L., Firuzi O., Miri R. // Drug Des. Dev. Ther. 2017. Vol. 11. P. 407. doi: 10.2147/DDDT.S119995
  8. Mennatallah A.S., Ali A.E., Nadia S.E. // Bioorg. Chem. 2020. Vol. 99. Article ID 103831. doi 10.1016/ j.bioorg.2020.103831
  9. Kumar A., Sharma S., Tripathi V.D., Maurya R.A., Srivastava S.P., Bhatia G., Tamrakar A.K., Srivastava A.K. // Bioorg. Med. Chem. 2010. Vol. 18. P. 4138. doi 10.1016/ j.bmc.2009.11.061
  10. Safak C., Erdemli I., Sunal R. // Arzneimittel-forschung. 1993. Vol. 43. P. 1052.
  11. Пат. 2403243 (2010). РФ
  12. Nagarapu L., Dharani Kumari M., Vijaya Kumari N., Kantevari S. // Catal. Commun. 2007. Vol. 8. N 12. P. 1871. doi: 10.1016/j.catcom.2007.03.004
  13. Гейн В.Л., Казанцева М.И., Курбатова А.А. // ЖОрХ. 2011. Т. 47. № 6. С. 17; Gein V.L., Kazantseva M.I., Kurbatova A.A. // Russ. J. Org. Chem. 2011. Vol. 47. N 6. P. 886. doi: 10.1134/S1070428011060091
  14. Гейн В.Л., Казанцева М.И., Курбатова А.А. Вахрин М.И. // ХГС. 2010. Т. 46. № 5. С. 629; Gein V.L., Kazantseva, M.I., Kurbatova, A.A., Vahrin M.I. // Chem. Heterocycl. Compd. 2010. Vol. 46. N 5. P. 629. doi: 10.1007/s10593-010-0560-8
  15. Чебанов В.А., Сараев В.Е., Кобзарь К.М., Десенко С.М., Орлов В.Д., Гура Е.А. // ХГС. 2004. № 4. С. 571; Chebanov V.A., Saraev V.E., Kobzaŕ K.M., Desenko S.M., Gura E.A., Orlov V.D. // Chem. Heterocycl. Compd. 2004. Vol. 40. N 4. P. 475. doi: 10.1023/B:COHC.0000033541.49115.a0
  16. Yü S.-J., Wu S., Zhao X.-M., Lü C.-W. // Res. Chem. Intermed. 2017. Vol. 43. P. 3121. doi: 10.1007/s11164-016-2814-2
  17. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET).
  18. Sheldrick G.M. // Acta Crystallogr. (A). 2008. Vol. 64. P. 112. doi: 10.1107/S0108767307043930
  19. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. P. 3. doi: 10.1107/S2053229614024218
  20. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H. // J. Appl. Cryst. 2009. Vol. 42. P. 339. doi: 10.1107/S0021889808042726

Supplementary files

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2. Scheme 1. R = Ph (5a), 4-FC6H4 (5б), 2-FC6H4 (5в), 4-ClC6H4 (5г), 2-ClC6H4 (5д), 4-BrC6H4 (5е), 2-BrC6H4 (5ж), 3-NO2C6H4 (5з), 4-MeC6H4 (5и), 4-EtC6H4 (5к), 4-i-PrC6H4 (5л), 4-i-BuC6H4 (5м), 4-MeOC6H4 (5н), 3-C5H4N (5о), 4-NO2C6H4 (5п).

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3. Scheme 2.

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4. Scheme 3.

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5. Fig.1. General view of the molecule of compound 5z in a crystal, represented by thermal ellipsoids with a 30% probability.

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