Skip to main content
SpringerLink
Log in

Synthesis and anti-inflammatory activity of N-arylamides of 4-aryl- and 4-(thiophen-2-yl)-2-[2-(furan-2-carbonyl)hydrazono]-4-oxobutanoic acids

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

N-Arylamides of 4-aryl/4-(thiophen-2-yl)-2-[2-(furan-2-carbonyl)hydrazono]-4-oxobutanoic acids were synthesized by the reaction of N′-(5-aryl/5-(thiophen-2-yl)-2-oxofuran-3(2H)-ylidene)furan-2-carbohydrazides with arylamines and evaluated for antiinflammatory activity.

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

Similar content being viewed by others

References

  1. J. Tomassini, H. Selnick, M. E. Davies, M. E. Armstrong, J. Baldwin, M. Bourgeois, J. Hastings, D. Hazuda, J. Lewis, W. McClements, Antimicrob. Agents Chemother., 1994, 38, 2827; DOI: https://doi.org/10.1128/AAC.38.12.2827.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. B. M. Baughman, P. Jake Slavish, R. M. DuBois, V. A. Boyd, S. W. White, T. R. Webb, ACS Chem. Biol., 2012, 7, 526; DOI: https://doi.org/10.1021/cb200439z.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. A. Dias, D. Bouvier, T. Crépin, A. A. McCarthy, D. J. Hart, F. Baudin, S. Cusack, R. W. H. Ruigrok, Nature, 2009, 458, 914; DOI: https://doi.org/10.1038/nature07745.

    Article  CAS  PubMed  Google Scholar 

  4. E. Kowalinski, C. Zubieta, A. Wolkerstorfer, O. H. J. Szolar, R. W. H. Ruigrok, S. Cusack, PLOS Pathog., 2012, 8, e1002831; DOI: https://doi.org/10.1371/journal.ppat.1002831.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. V. Uchil, B. Seo, V. Nair, J. Org. Chem., 2007, 72, 8577; DOI: https://doi.org/10.1021/jo701336r.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. X.-H. Jiang, Y.-Q. Long, Chin. J. Chem., 2004, 22, 978; DOI: https://doi.org/10.1002/cjoc.20040220920.

    Article  CAS  Google Scholar 

  7. Z. Michelini, C. M. Galluzzo, D. R. M. Negri, P. Leone, R. Amici, R. Bona, V. Summa, R. Di Santo, R. Costi, Y. Pommier, C. Marchand, L. Palmisano, S. Vella, A. Cara, J. Virol. Methods, 2010, 168, 272; DOI: https://doi.org/10.1016/j.jviromet.2010.06.004.

    Article  CAS  PubMed  Google Scholar 

  8. E. B. de Melo, M. M. C. Ferreira, J. Chem. Inf. Model., 2012, 52, 1722; DOI: https://doi.org/10.1021/ci300039a.

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  10. C. A. Shaw-Reid, V. Munshi, P. Graham, A. Wolfe, M. Witmer, R. Danzeisen, D. B. Olsen, S. S. Carroll, M. Embrey, J. S. Wai, M. D. Miller, J. L. Cole, D. J. Hazuda, J. Biol. Chem., 2003, 278, 2777; DOI: https://doi.org/10.1074/jbc.C200621200.

    Article  CAS  PubMed  Google Scholar 

  11. V. Summa, A. Petrocchi, P. Pace, V. G. Matassa, R. De Francesco, S. Altamura, L. Tomei, U. Koch, P. Neuner, J. Med. Chem., 2004, 47, 14; DOI: https://doi.org/10.1021/jm0342109.

    Article  CAS  PubMed  Google Scholar 

  12. R. Braga, L. Hecquet, C. Blonski, Bioorg. Med. Chem., 2004, 12, 2965; DOI: https://doi.org/10.1016/j.bmc.2004.03.039.

    Article  CAS  PubMed  Google Scholar 

  13. S. Liu, L.-F. Zeng, L. Wu, X. Yu, T. Xue, A. M. Gunawan, Y.-Q. Long, Z.-Y. Zhang, J. Am. Chem. Soc., 2008, 130, 17075; DOI: https://doi.org/10.1021/ja8068177.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. C. Paz, M. G. Peter, B. Schmidt, J. Becerra, M. Guti-érrez, L. Astudillo, M. Silva, J. Chil. Chem. Soc., 2012, 57, 1292; DOI: https://doi.org/10.4067/S0717-97072012000300020.

    Article  CAS  Google Scholar 

  15. A. I. Siutkina, N. M. Igidov, M. V. Dmitriev, R. R. Makhmudov, V. V. Novikova, Russ. J. Gen. Chem., 2019, 89, 1388; DOI: https://doi.org/10.1134/S1070363219070065.

    Article  CAS  Google Scholar 

  16. I. A. Kizimova, N. M. Igidov, M. V. Dmitriev, S. V. Chashchina, R. R. Makhmudov, A. I. Siutkina, Russ. J. Gen. Chem., 2019, 89, 2345; DOI: https://doi.org/10.1134/S107036321912003X.

    Article  CAS  Google Scholar 

  17. S. A. Shipilovskikh, V. Yu. Vaganov, R. R. Makhmudov, A. E. Rubtsov, Russ. J. Gen. Chem., 2020, 90, 583; DOI: https://doi.org/10.1134/S1070363220040040.

    Article  CAS  Google Scholar 

  18. I. A. Gorbunova, Yu. O. Sharavyeva, R. R. Makhmudov, D. A. Shipilovskikh, V. M. Shadrin, N. A. Pulina, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2022, 92, 1899; DOI: https://doi.org/10.1134/S1070363222100048.

    Article  CAS  Google Scholar 

  19. S. N. Igidov, A. Yu. Turyshev, R. R. Makhmudov, D. A. Shipilovskikh, M. V. Dmitriev, O. V. Zvereva, P. S. Silaichev, N. M. Igidov, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2023, 93, 253; DOI: https://doi.org/10.1134/S1070363223020044.

    Article  CAS  Google Scholar 

  20. A. I. Siutkina, Yu. O. Sharavyeva, S. V. Chashchina, S. A. Shipilovskikh, N. M. Igidov, Russ. Chem. Bull., 2022, 71, 496; DOI: https://doi.org/10.1007/s11172-022-3439-9.

    Article  CAS  Google Scholar 

  21. B. J. Drakulić, M. Stavri, S. Gibbons, Ž. S. Žižak, T. ž. Verbić, I. O. Juranić, M. Zloh, Chem. Med. Chem., 2009, 4, 1971; DOI: https://doi.org/10.1002/cmdc.200900273.

    Article  PubMed  Google Scholar 

  22. Yu. O. Sharavyeva, A. I. Siutkina, S. V. Chashchina, V. V. Novikova, R. R. Makhmudov, S. A. Shipilovskikh, Russ. Chem. Bull., 2022, 71, 538; DOI: https://doi.org/10.1007/s11172-022-3445-y.

    Article  CAS  Google Scholar 

  23. C. Paz, D. Cajas-Madriaga, C. Torres, Y. Moreno, M. J. Fernández, J. Becerra, M. Silva, J. Chil. Chem. Soc., 2013, 58, 1713; DOI: https://doi.org/10.4067/S0717-97072013000200015.

    Article  CAS  Google Scholar 

  24. I. A. Gorbunova, V. M. Shadrin, N. A. Pulina, V. V. Novikova, S. S. Dubrovina, D. A. Shipilovskikh, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2023, 93, 9; DOI: https://doi.org/10.1134/S1070363223010024.

    Article  Google Scholar 

  25. D. V. Lipin, E. I. Denisova, D. A. Shipilovskikh, R. R. Makhmudov, N. M. Igidov, S. A. Shipilovskikh, Russ. J. Org. Chem., 2022, 58, 1354; DOI: https://doi.org/10.1134/S1070428022120041.

    Article  Google Scholar 

  26. A. Rogova, I. A. Gorbunova, T. E. Karpov, R. Yu. Sidorov, N. Domracheva, A. E. Rubtsov, D. A. Shipi-lovskikh, A. R. Muslimov, M. V. Zyuzin, A. S. Timin, S. A. Shipilovskikh, Eur. J. Med. Chem., 2023, 115325; DOI: https://doi.org/10.1016/j.ejmech.2023.115325.

  27. E. Gunina, N. Zhestkij, S. Bachinin, S. P. Fisenko, D. A. Shipilovskikh, V. A. Milichko, S. A. Shipilovskikh, Photonics Nanostruct. — Fundam. Appl., 2022, 48, 100990; DOI: https://doi.org/10.1016/j.photonics.2021.100990.

    Article  Google Scholar 

  28. N. A. Zhestkij, E. V. Gunina, S. P. Fisenko, A. E. Rubtsov, D. A. Shipilovskikh, V. A. Milichko, S. A. Shipilovskikh, Chim. Techno Acta, 2021, 8, 20218411; DOI: https://doi.org/10.15826/chimtech.2021.8.4.11.

    Article  CAS  Google Scholar 

  29. D. V. Lipin, E. I. Denisova, I. O. Devyatkin, E. A. Okoneshnikova, D. A. Shipilovskikh, R. R. Makh-mudov, N. M. Igidov, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2022, 91, 2469; DOI: https://doi.org/10.1134/s1070363221120161.

    Article  Google Scholar 

  30. E. I. Denisova, D. V. Lipin, K. Yu. Parkhoma, I. O. Devyatkin, D. A. Shipilovskikh, S. V. Chashchina, R. R. Makhmudov, N. M. Igidov, S. A. Shipilovskikh, Russ. J. Org. Chem., 2022, 57, 1955; DOI: https://doi.org/10.1134/s1070428021120083.

    Article  Google Scholar 

  31. I. A. Gorbunova, D. A. Shipilovskikh, A. E. Rubtsov, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2021, 91, 1623; DOI: https://doi.org/10.1134/s1070363221090048.

    Article  Google Scholar 

  32. I. A. Kizimova, N. M. Igidov, M. A. Kiselev, D. V. Ivanov, A. I. Syutkina, Russ. J. Gen. Chem., 2020, 90, 815; DOI: https://doi.org/10.1134/S1070363220050096.

    Article  CAS  Google Scholar 

  33. M. A. Kiselev, N. M. Igidov, Y. S. Toksarova, I. N. Chernov, A. E. Rubtsov, Russ. J. Org. Chem., 2017, 53, 920; DOI: https://doi.org/10.1134/S1070428017060173.

    Article  CAS  Google Scholar 

  34. S. S. Zykova, A. A. Darovskikh, T. F. Odegova, M. A. Kiselev, N. M. Igidov, Pharm. Chem. J., 2016, 49, 657; DOI: https://doi.org/10.1007/s11094-016-1347-8.

    Article  CAS  Google Scholar 

  35. S. S. Zykova, A. R. Galembikova, B. R. Ramazanov, T. F. Odegova, N. M. Igidov, M. A. Kiselev, S. V. Boichuk, Pharm. Chem. J., 2016, 49, 817; DOI: https://doi.org/10.1007/s11094-016-1378-1.

    Article  CAS  Google Scholar 

  36. I. A. Kizimova, N. M. Igidov, M. A. Kiselev, M. V. Dmitriev, S. V. Chashchina, A. I. Siutkina, Russ. J. Gen. Chem., 2020, 90, 182; DOI: https://doi.org/10.1134/S1070363220020036.

    Article  CAS  Google Scholar 

  37. S. S. Zykova, I. A. Kizimova, A. I. Syutkina, Yu. S. Toksarova, N. M. Igidov, D. F. Ibishov, S. V. Boichuk, P. D. Dunaev, A. R. Galembikova, R. R. Korochkina, Pharm. Chem. J., 2020, 53, 895; DOI: https://doi.org/10.1007/s11094-020-02096-z.

    Article  CAS  Google Scholar 

  38. S. Boichuk, A. Galembikova, K. Syuzov, P. Dunaev, F. Bikinieva, A. Aukhadieva, S. Zykova, N. Igidov, K. Gankova, M. Novikova, P. Kopnin, Molecules, 2021, 26, 5780; DOI: https://doi.org/10.3390/molecules26195780.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. S. Boichuk, K. Syuzov, F. Bikinieva, A. Galembikova, S. Zykova, K. Gankova, S. Igidov, N. Igidov, Molecules, 2022, 27, 2873; DOI: https://doi.org/10.3390/molecules27092873.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. S. A. Shipilovskikh, A. E. Rubtsov, J. Org. Chem., 2019, 84, 15788; DOI: https://doi.org/10.1021/acs.joc.9b00711.

    Article  CAS  PubMed  Google Scholar 

  41. A. I. Siutkina, S. V. Chashchina, R. R. Makhmudov, I. A. Kizimova, S. A. Shipilovskikh, N. M. Igidov, Russ. J. Org. Chem., 2021, 57, 1874; DOI: https://doi.org/10.1134/S1070428021110105.

    Article  CAS  Google Scholar 

  42. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lecarstvennykh sredstv [Guidelines for Preclinical Trials of Medications], Ed. A. N. Mironov, Grif and Co., Moscow, 2012, p. 509 (in Russian).

    Google Scholar 

  43. S. N. Igidov, A. Yu. Turyshev, R. R. Makhmudov, D. A. Shipilovskikh, N. M. Igidov, S. A. Shipilovskikh, Russ. J. Gen. Chem., 2022, 92, 1629; DOI: https://doi.org/10.1134/S1070363222090067.

    Article  CAS  Google Scholar 

  44. S. N. Igidov, I. A. Gorbunova, A. Y. Turyshev, D. A. Shipilovskikh, D. A. Kozlov, A. S. Rogova, R. R. Makhmudov, P. S. Silaichev, N. M. Igidov, Chim. Techno Acta, 2022, 10, 202310101; DOI: https://doi.org/10.15826/chimtech.2023.10.1.01.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation, 101 ul. Ekaterininskaya, 614990, Perm, Russian Federation

    S. N. Igidov, A. Yu. Turyshev, S. V. Chashchina, O. V. Zvereva & N. M. Igidov

  2. Merck LLC, 35 ul. Vavilova, 115054, Moscow, Russian Federation

    S. N. Igidov

  3. Perm State National Research University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    S. V. Chashchina, P. S. Silaichev & S. A. Shipilovskikh

  4. Perm National Research Polytechnic University, 29 Komsomolsky prosp., 614990, Perm, Russian Federation

    D. A. Shipilovskikh

  5. Scientific Research Institute of Chemistry, Lobachevsky State University of Nizhny Novgorod, 23 prosp. Gagarina, 603950, Nizhny Novgorod, Russian Federation

    I. N. Chernov

  6. School of Physics and Engineering, ITMO University, Build. A, 49 Kronverksky prosp., 197101, St. Petersburg, Russian Federation

    S. A. Shipilovskikh

Authors
  1. S. N. Igidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Turyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Chashchina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. A. Shipilovskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. N. Chernov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. V. Zvereva
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. P. S. Silaichev
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. N. M. Igidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. 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 authors declare no competing interests.

Additional information

This study was performed under financial support of the “Rational Use of the Earth Interior” Perm Scientific Educational Center 2023.

All experiments involving animals were carried out in accordance with the guidelines42 in compliance with the ethical rules (Protocol of the Commission on Bioethics at the PGFA No. 03/21-z dated November 11, 2021). The maintenance of the animals complied the rules of good laboratory practice during preclinical studies in the Russian Federation (State Standard GOST 33044–2014 “Principles of Good Laboratory Practice”) and the Order of the Ministry of Health of the Russian Federation dated April 01, 2016, No. 199n “On Approval of the Rules of Good Laboratory Practice”.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2241—2248, September, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Igidov, S.N., Turyshev, A.Y., Chashchina, S.V. et al. Synthesis and anti-inflammatory activity of N-arylamides of 4-aryl- and 4-(thiophen-2-yl)-2-[2-(furan-2-carbonyl)hydrazono]-4-oxobutanoic acids. Russ Chem Bull 72, 2241–2248 (2023). https://doi.org/10.1007/s11172-023-4021-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4021-9

Key words

Search

Navigation