Skip to main content
Log in

5-Hydroxy-1-phenylimidazolidine-2-thione as a new amidoalkylating agent for heterocyclic compounds

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

We showed a possibility of using 5-hydroxy-1-phenylimidazolidine-2-thione as an amidoalkylating agent in the reactions with 1-methyloxindole, 3-pyrazolone, and pyrazole derivatives to obtain a number of new unsymmetric bis-heterocyclic compounds with a direct C-C bond containing a combination of pharmacophoric groups of two classes of heterocycles.

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

Access this article

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

Instant access to the full article PDF.

References

  1. G. V. Zyryanov, D. S. Kopchuk, I. S. Kovalev, S. Santra, M. Rahman, A. F. Khasanov, A. P. Krinochkin, O. S. Taniya, O. N. Chupakhin, V. N. Charushin, Mendeleev Commun., 2020, 30, 537; DOI: https://doi.org/10.1016/j.mencom.2020.09.001.

    Article  CAS  Google Scholar 

  2. E. S. Matyugina, A. L. Khandazhinskaya, S. N. Kochetkov, K. L. Seley-Radtke, Mendeleev Commun., 2020, 30, 231; DOI: https://doi.org/10.1016/j.mencom.2020.03.034.

    Article  CAS  Google Scholar 

  3. M. A. J. Duncton, Med. Chem. Commun., 2011, 2, 1135; DOI: https://doi.org/10.1039/c1md00134e.

    Article  CAS  Google Scholar 

  4. S. Archana, R. Ranganathan, M. Dinesh, P. Arul, A. Ponnuswamy, P. Kalaiselvi, S. Chellammal, G. Subramanian, Res. Chem. Intermed., 2017, 43, 2471; DOI https://doi.org/10.1007/s11164-016-2774-6.

    Article  CAS  Google Scholar 

  5. Z. Najafi, M. Mahdavi, M. Safavi, M. Saeedi, H. Alinezhad, M. Pordeli, S. K. Ardestani, A. Shafiee, A. Foroumadi, T. Akbarzadeh, J. Heterocycl. Chem., 2015, 52, 1743; DOI: https://doi.org/10.1002/jhet.2273.

    Article  CAS  Google Scholar 

  6. J. C. Reader, T. P. Matthews, S. Klair, K.-M. J. Cheung, J. Scanlon, N. Proisy, G. Addison, J. Ellard, N. Piton, S. Taylor, M. Cherry, M. Fisher, K. Boxall, S. Burns, M. I. Walton, I. M. Westwood, A. Hayes, P. Eve, M. Valenti, A. de Haven Brandon, G. Box, R. L. M. van Montfort, D. H. Williams, G. W. Aherne, F. I. Raynaud, S. A. Eccles, M. D. Garrett, I. Collins, J. Med. Chem., 2011, 54, 8328; DOI: https://doi.org/10.1021/jm2007326.

    Article  CAS  Google Scholar 

  7. P. S. Lemport, V. A. Roznyatovsky, B. N. Tarasevich, O. V. Khromova, V. N. Khrustalev, I. B. Rozentsveig, V. G. Nenajdenko, Mendeleev Commun., 2019, 29, 529; DOI: https://doi.org/10.1016/j.mencom.2019.09.017.

    Article  CAS  Google Scholar 

  8. M. A. Epishina, A. S. Kulikov, L. L. Fershtat, I. V. Ananyev, N. N. Makhova, Mendeleev Commun., 2019, 29, 288; DOI: https://doi.org/10.1016/j.mencom.2019.05.015.

    Article  CAS  Google Scholar 

  9. G. A. Selivanova, E. V. Tretyakov, Russ. Chem. Bull., 2020, 69, 838; DOI: https://doi.org/10.1007/s11172-020-2842-3.

    Article  CAS  Google Scholar 

  10. J. K. Aulakh, T. S. Lobana, H. Sood, D. S. Arora, I. Garcia-Santos, M. Kaur, J. P. Jasinski, Polyhedron, 2020, 175, 114235; DOI: https://doi.org/10.1016/j.poly.2019.114235.

    Article  Google Scholar 

  11. J. K. Aulakh, T. S. Lobana, H. Sood, D. S. Arora, R. Kaur, J. Singh, I. Garcia-Santos, M. Kaur, J. P. Jasinski, RSC Adv., 2019, 9, 15470; DOI: https://doi.org/10.1039/c9ra01804b.

    Article  CAS  Google Scholar 

  12. T. S. Lobana, J. K. Aulakh, H. Sood, D. S. Arora, I. Garcia-Santos, M. Kaur, C. E. Duff, J. P. Jasinski, New J. Chem., 2018, 42, 9886; DOI: https://doi.org/10.1039/C8NJ00206A.

    Article  CAS  Google Scholar 

  13. A. I. El-Shenawy, Russ. J. Bioorg. Chem., 2016, 42, 100; DOI: https://doi.org/10.1134/S1068162016010040.

    Article  CAS  Google Scholar 

  14. H. Beyzaei, S. Kooshki, R. Aryan, M. M. Zahedi, A. Samzadeh-Kermani, B. Ghasemi, M. Moghaddam-Manesh, Appl. Biochem. Biotechnol., 2018, 184, 291; DOI: https://doi.org/10.1007/s12010-017-2544-y.

    Article  CAS  Google Scholar 

  15. P. Thanigaimalai, L. Ki-Cheul, B. Seong-Cheol, L. Jee-Hyun, Y. Cheong-Yong, R. Eunmiri, H. Bang-Yeon, K. Youngsoo, J. Sang-Hun, Bioorg. Med. Chem., 2018, 18, 1135; DOI: https://doi.org/10.1016/j.bmc.2009.12.044.

    Article  Google Scholar 

  16. T. R. de Moura, S. L. Cavalcanti, P. R. D. V. de Godoy, E. T. Sakamoto-Hojo, F. V. Rocha, E. T. de Almeida, V. M. Deflon, A. E. Mauro, A. V. G. Netto, Transit. Met. Chem., 2017, 42, 565; DOI: https://doi.org/10.1007/s11243-017-0161-9.

    Article  CAS  Google Scholar 

  17. N. Nisha, P. Singh, D. T. Hendricks, K. Bisetty, V. Kumar, Synlett, 2013, 24, 1865; DOI: https://doi.org/10.1055/s-0033-1339315.

    Article  CAS  Google Scholar 

  18. S. Cesarini, A. Spallarossa, A. Ranise, S. Schenone, C. Rosano, P. La Colla, G. Sanna, B. Busonera, R. Loddo, Eur. J. Med. Chem., 2009, 44, 1106; DOI: https://doi.org/10.1016/j.ejmech.2008.06.010.

    Article  CAS  Google Scholar 

  19. P. F. Espuri, L. L. Dos Reis, E. de Figueiredo Peloso, V. S. Gontijo, F. A. Colombo, J. B. Nunes, C. E. de Oliveira, E. T. De Almeida, D. E. S. Silva, J. Bortoletto, D. F. Segura, A. V. G. Netto, M. J. Marques, J. Biol. Inorg. Chem., 2019, 24, 419; DOI: https://doi.org/10.1007/s00775-019-01657-2.

    Article  CAS  Google Scholar 

  20. V. A. Ivolgina, L. D. Popov, G. A. Gazieva, A. N. Kravchenko, Russ. Chem. Bull., 2020, 69, 2215; DOI: https://doi.org/10.1007/s11172-020-3024-z.

    Article  CAS  Google Scholar 

  21. R. Mazurkiewiczl, A. Pazdzierniok-Holewa, J. Adamek, K. Zielińska, Adv. Heterocycl. Chem., 2014, 111, 43; DOI: https://doi.org/10.1016/B978-0-12-420160-6.00002-1.

    Article  Google Scholar 

  22. O. N. Gorunova, INEOS OPEN, 2021, 4, 90; DOI: https://doi.org/10.32931/io2113r.

    CAS  Google Scholar 

  23. L. A. Sviridova, S. V. Afanas’eva, G. A. Golubeva, P. B. Terent’ev, Yu. G. Bundel’, Chem. Heterocycl. Compd., 1990, 26, 1008; DOI: https://doi.org/10.1007/BF00472482.

    Article  Google Scholar 

  24. I. V. Dlinnykh, G. A. Golubeva, I. F. Leshcheva, V. V. Nesterov, M. Yu. Antipin, L. A. Sviridova, Chem. Heterocycl. Compd., 2004, 40, 1142; DOI: https://doi.org/10.1023/B:COHC.0000048286.22570.9f.

    Article  CAS  Google Scholar 

  25. L. A. Sviridova, G. A. Golubeva, I. V. Dlinnykh, Chem. Heterocycl. Compd., 1996, 32, 1430; DOI: https://doi.org/10.1007/BF01169975.

    Article  Google Scholar 

  26. V. Sadovoy, A. E. Kovrov, G. A. Golubeva, L. A. Sviridova, Chem. Heterocycl. Compd., 2011, 46, 1215; DOI: https://doi.org/10.1007/s10593-011-0655-x.

    Article  CAS  Google Scholar 

  27. L. A. Sviridova, P. S. Protopopova, M. G. Akimov, P. V. Dudina, E. K. Melnikova, K. A. Kochetkov, Mendeleev Commun., 2020, 30, 347; DOI: https://doi.org/10.1016/j.mencom.2020.05.029.

    Article  CAS  Google Scholar 

  28. S. Cortes, H. Kohn, J. Org. Chem., 1983, 48, 2246; DOI: https://doi.org/10.1021/jo00161a021.

    Article  CAS  Google Scholar 

  29. L. A. Sviridova, G. A. Golubeva, A. N. Tavtorkin, Yu. V. Nelyubina, K. A. Kochetkov, Chem. Heterocycl. Compd., 2008, 44, 542; DOI: https://doi.org/10.1007/s10593-008-0073-x.

    Article  CAS  Google Scholar 

  30. H. Handa, Y. Fu, T. Baba, Y. Ono, Catalysis Lett., 1999, 59, 195; DOI: https://doi.org/10.1023/A:1019093126342.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. A. Kochetkov.

Ethics declarations

The authors declare no competing interests.

Additional information

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation using the equipment of the Center for Molecular Structure Studies at the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 587–590, March, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kochetkov, K.A., Gorunova, O.N. & Bystrova, N.A. 5-Hydroxy-1-phenylimidazolidine-2-thione as a new amidoalkylating agent for heterocyclic compounds. Russ Chem Bull 71, 587–590 (2022). https://doi.org/10.1007/s11172-022-3454-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3454-x

Key words

Navigation