Skip to main content
SpringerLink
Log in

Synthesis and Antinociceptive Activity of Substituted 5-(Het)aryl-3-(4-methylbenzoyl)hydrazono-3H-furan-2-ones

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The method was proposed for the synthesis of new substituted 5-(het)aryl-3-(4-methylbenzoyl)hydrazono-3H-furan-2-ones by intramolecular cyclization of 2-[2-(4-methylbenzoyl)hydrazono]-4-oxobut-2-enoic acids in the presence of propionic anhydride. The antinociceptive activity of the obtained compounds was studied.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Ivashchenko, A.A., Mitkin, O.D., Jones, J.C., Nikitin, A.V., Koryakova, A.G., Ryakhovskiy, A., Karapetian, R.N., Kravchenko, D.V., Aladinskiy, V., Leneva, I.A., Falynskova, I.N., and Glubokova, E.A., J. Med. Chem., 2020, vol. 63, p. 9403. https://doi.org/10.1021/acs.jmedchem.0c00565

    Article  CAS  PubMed  Google Scholar 

  2. Mayorova, O.A., and Yegorova, A.Y., Magn. Reson. Chem., 2015, vol. 10, p. 853. https://doi.org/10.1002/mrc.4270

    Article  CAS  Google Scholar 

  3. Gavkus, D.N., Maiorova, O.A., Borisov, M.Y., and Egorova, A.Y., Russ. J. Org. Chem., 2012, vol. 48, p. 1229. https://doi.org/10.1134/s107042801209014x

    Article  CAS  Google Scholar 

  4. Shipilovskikh, S.A. and Rubtsov, A.E., J. Org. Chem., 2019, vol. 84, p. 15788. https://doi.org/10.1021/acs.joc.9b00711

    Article  CAS  PubMed  Google Scholar 

  5. Sayed, H.H., Hashem, A.I., Yousif, N.M., and ElSayed, W.A., Arch. Pharm., 2007, vol. 6, p. 315. https://doi.org/10.1002/ardp.200700043

    Article  CAS  Google Scholar 

  6. Dias, A., Bouvier, D., Crepin, T., McCarthy, A.A., Hart, D.J., Baudin, F., Cusack, S., and Ruigrok, R.W., Nature, 2009, vol. 458, p. 914. https://doi.org/10.1038/nature07745

    Article  CAS  PubMed  Google Scholar 

  7. Fernández-García, Y., Horst, S., Bassetto, M., Brancale, A., Neyts, J., Rogolino, D., Sechi, M., Carcelli, M., Günther, S., and Rocha-Pereira, J., Antivir. Res., 2020, vol. 183, p. 104947. https://doi.org/10.1016/j.antiviral.2020.104947

    Article  CAS  PubMed  Google Scholar 

  8. Joksimović, N., Janković, N., Davidović, G., and Bugarčić, Z., Bioorg. Chem., 2020, vol. 105, p. 104343. https://doi.org/10.1016/j.bioorg.2020.104343

    Article  CAS  PubMed  Google Scholar 

  9. Nair, V. and Okello, M., Molecules, 2015, vol. 20, p. 12623. https://doi.org/10.3390/molecules200712623

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Sharma, H., Sanchez, T.W., Neamati, N., Detorio, M., Schinazi, R.F., Cheng, X., and Buolamwini, J.K., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6146. https://doi.org/10.1016/j.bmcl.2013.09.009

    Article  CAS  PubMed  Google Scholar 

  11. Bobrovskaya, O.V., Russkih, A.A., Yankin, A.N., Dmitriev, M.V., Bunev, A.S., and Gein, V.L., Synth. Commun., 2021, vol. 51, p. 1731. https://doi.org/10.1080/00397911.2021.1903930

    Article  CAS  Google Scholar 

  12. Sobin, F.V., Pulina, N.A., Lipatnikov, K.V., Starkova, A.V., Yushkova, T.A., and Naugol’nykh, E.A., Pharm. Chem. J., 2021, vol. 54, p. 1003. https://doi.org/10.1007/s11094-021-02310-6

    Article  CAS  Google Scholar 

  13. Gein, V.L., Zamaraeva, T.M., Gorgopina, E.V., and Dmitriev, M.V., Chem. Heterocycl. Compd., 2020, vol. 56, p. 339. https://doi.org/10.1007/s10593-020-02665-w

    Article  CAS  Google Scholar 

  14. Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Gen. Chem., 2020, vol. 90, p. 943. https://doi.org/10.1134/S1070363220060031

    Article  CAS  Google Scholar 

  15. Igidov, N.M., Kiselev, M.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 526. https://doi.org/10.1134/S1070428016040084

    Article  CAS  Google Scholar 

  16. Shipilovskikh, S.A., Vaganov, V.Y., Makhmudov, R.R., and Rubtsov, A.E., Russ. J. Gen. Chem., 2020, vol. 90, p. 583. https://doi.org/10.1134/S1070363220040040

    Article  CAS  Google Scholar 

  17. Shipilovskikh, S.A., Makhmudov, R.R., Lupach, D.Yu., Pavlov, P.T., Babushkina, E.V., and Rubtsov, A.E., Pharm. Chem. J., 2013, vol. 47, p. 366. https://doi.org/10.1007/s11094-013-0960-z

    Article  CAS  Google Scholar 

  18. Kizimova, I.A., Igidov, N.M., Chaschina, S.V., Chernov, I.N., and Rubtsov, A.E., Russ. J. Org. Chem., 2021, vol. 55, no. 11, p. 1704. https://doi.org/10.1134/S1070428019110101

    Article  Google Scholar 

  19. Mironov, A.N., Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh veshchestv (Guidelines for Conducting Preclinical Studies of Medicinal Substances), Moscow: Grif i K, 2012, p. 509.

  20. Belen’kii, M.L., Elementy kolichestvennoi otsenki farmakologicheskogo effekta (Elements of a Quantitative Assessment of the Pharmacological Effect), Leningrad: Medgiz, 1963, p. 146.

Download references

Funding

This was financially supported by the Perm Scientific and Educational Center “Rational Subsoil Use,” 2021.

Author information

Authors and Affiliations

  1. Perm State University, 614990, Perm, Russia

    D. V. Lipin, E. I. Denisova, Е. А. Okoneshnikova, D. A. Shipilovskikh, R. R. Makhmudov & S. A. Shipilovskikh

  2. Perm State Pharmaceutical Academy, 614990, Perm, Russia

    E. I. Denisova, I. О. Devyatkin & N. M. Igidov

  3. Perm National Research Polytechnic University, 614990, Perm, Russia

    D. A. Shipilovskikh

  4. Federal Research Center for Medical and Preventive Technologies for Managing Public Health Risks, 614045, Perm, Russia

    R. R. Makhmudov

  5. ITMO University, School of Physics and Engineering, 197101, St. Petersburg, Russia

    S. A. Shipilovskikh

Authors
  1. D. V. Lipin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. I. Denisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. О. Devyatkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Е. А. Okoneshnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. A. Shipilovskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. R. R. Makhmudov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. M. Igidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. S. A. Shipilovskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Shipilovskikh.

Ethics declarations

The studies were performed in accordance with all applicable international, national and institutional guidelines for the care and use of animals.

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lipin, D.V., Denisova, E.I., Devyatkin, I.О. et al. Synthesis and Antinociceptive Activity of Substituted 5-(Het)aryl-3-(4-methylbenzoyl)hydrazono-3H-furan-2-ones. Russ J Gen Chem 91, 2469–2474 (2021). https://doi.org/10.1134/S1070363221120161

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221120161

Keywords:

Search

Navigation