Skip to main content
SpringerLink
Log in

5-Arylmethylidene-2-iminothiazolidin-4-ones in the synthesis of novel dispiro-fused oxindolepyrrolidineiminothiazolidinones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel series of dispiro(indolinonepyrrolidineiminothiazolidinones) were synthesized by 1,3-dipolar cycloaddition of 5-arylmethylidene-2-iminothiazolidin-4-ones and azomethine ylides generated from N-alkylamino acids and isatin derivatives. A number of iminothiazolidinones and dispiro compounds were tested for antiproliferative activity. Seven compounds showed moderate antiproliferative activity at micromolar concentrations against cancer cell lines.

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

Figure. 1.
Figure 2.

Similar content being viewed by others

References

  1. (a) Nirwan, S.; Chahal, V.; Kakkar, R. J. Heterocycl. Chem. 2019, 56, 1239. (b) Mech, D.; Kurowska, A.; Trotsko, N. Int. J. Mol. Sci. 2021, 22, 11533. (c) Kumar, H.; Aggarwal, N.; Marwaha, M. G.; Deep, A.; Chopra, H.; Matin, M. M.; Roy, A.; Emran, T. B.; Mohanta, Y. K.; Ahmed, R.; Mohanta, T. K.; Saravanan, M.; Marwaha, R. K.; Al-Harrasi, A. Molecules 2022, 27, 6763. (d) Izmest'ev, A. N.; Streltsov, A. A.; Kravchenko, A. N.; Gazieva, G. A. Chem. Heterocycl. Compd. 2022, 58, 483.

  2. (a) Rabelo Pessoa de Siqueira, L.; Teixeira de Moraes Gomes, P. A.; de Lima Ferreira, L. P.; Barreto de Melo Rêgo, M. J.; Lima Leite, A. C. Eur. J. Med. Chem. 2019, 170, 237. (b) Szczepański, J.; Tuszewska, H.; Trotsko, N. Molecules 2022, 27, 3750. (c) Gazieva, G. A.; Izmest'ev, A. N. Chem. Heterocycl. Compd. 2015, 50, 1515. (d) Kovaleva, K.; Mamontova, E.; Yarovaya, O.; Zakharova, O.; Zakharenko, A.; Lavrik, O.; Salakhutdinov, N. Mol. Diversity 2021, 25, 2389.

  3. (a)Tratrat, C.; Petrou, A.; Geronikaki, A.; Ivanov, M.; Kostić, M.; Soković, M.; Vizirianakis, I. S.; Theodoroula, N. F.; Haroun, M. Molecules 2022, 27, 1930. (b) Trotsko, N. Eur. J. Med. Chem. 2021, 215, 113266.

  4. Levshin, I. B.; Simonov, A. Y.; Lavrenov, S. N.; Panov, A. A.; Grammatikova, N. E.; Alexandrov, A. A.; Ghazy, E. S. M. O.; Savin, N. A.; Gorelkin, P. V.; Erofeev, A. S.; Polshakov, V. I. Pharmaceuticals 2022, 15, 563.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Ma, L.; Xie, C.; Ma, Y.; Liu, J.; Xiang, M.; Ye, X.; Zheng, H.; Chen, Z.; Xu, Q.; Chen, T.; Chen, J.; Yang, J.; Qiu, N.; Wang, G.; Liang, X.; Peng, A.; Yang, S.; Wei, Y.; Chen L. J. Med. Chem. 2011, 54, 2060.

    Article  CAS  PubMed  Google Scholar 

  6. (a) Izmest'ev, A. N.; Gazieva, G. A.; Kolotyrkina, N. G.; Daeva, E. D.; Kravchenko, A. N. Chem. Heterocycl. Compd. 2020, 56, 1569. (b) Izmest'ev, A. N.; Streltsov, A. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Strelenko, Y. A.; Kravchenko, A. N.; Gazieva, G. A. ChemistrySelect 2022, 7, e202104128. (c) Song, Y.-X.; Du, D.-M. Org. Biomol. Chem. 2020, 18, 6018.

  7. (a) Murugan, R.; Anbazhagan, S.; Narayanan, S. S. Eur. J. Med. Chem. 2009, 44, 3272. (b) Toumi, A.; Boudriga, S.; Hamden, K.; Sobeh, M.; Cheurfa, M.; Askri, M.; Knorr, M.; Strohmann, C.; Brieger, L. Bioorg. Chem. 2021, 106, 104507.

  8. Beloglazkina, A. A.; Mazhuga, A. G.; Beloglazkina, E. K.; Mefedova, S. R.; Karpov, N. A. RU Patent 2730286 C1.

  9. (a) Izmest'ev, A. N.; Gazieva, G. A.; Karnoukhova, V. A.; Kravchenko, A. N. Org. Biomol. Chem. 2020, 18, 6905. (b) Izmest'ev, A. N.; Karnoukhova, V. A.; Larin, A. A.; Kravchenko, A. N.; Fershtat, L. L.; Gazieva, G. A. Int. J. Mol. Sci. 2022, 23, 13820.

  10. (a) Izmest'ev, A. N.; Vasileva, D. A.; Melnikova, E. K.; Kolotyrkina, N. G.; Borisova, I. A.; Kravchenko, A. N.; Gazieva, G. A. New J. Chem. 2019, 43, 1038. (b) Izmest'ev, A. N.; Gazieva, G. A.; Anikina, L. V.; Pukhov, S. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Kravchenko, A. N. New J. Chem. 2021, 45, 12271.

  11. Lafayette, E. A.; Vitalino de Almeida, S. M.; Cavalcanti Santos, R. V.; Ferreira de Oliveira, J.; da Cruz Amorim, C. A.; Ferreira da Silva, R. M.; Galdino da Rocha Pitta, M.; da Rocha Pitta, I.; de Moura, R. O.; Bezerra de Carvalho, L., Jr.; Barreto de Melo Rêgo, M. J.; Alves de Lima, M. d. C. Eur. J. Med. Chem. 2017, 136, 511.

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Alexei N. Izmest’ev, Andrey A. Streltsov, Angelina N. Kravchenko & Galina A. Gazieva

  2. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    Andrey A. Streltsov

Authors
  1. Alexei N. Izmest’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrey A. Streltsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Angelina N. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Galina A. Gazieva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Galina A. Gazieva.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 309–316

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 3556 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Izmest’ev, A.N., Streltsov, A.A., Kravchenko, A.N. et al. 5-Arylmethylidene-2-iminothiazolidin-4-ones in the synthesis of novel dispiro-fused oxindolepyrrolidineiminothiazolidinones. Chem Heterocycl Comp 59, 309–316 (2023). https://doi.org/10.1007/s10593-023-03198-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03198-8

Keywords

Search

Navigation