Skip to main content
Log in

Protolytic and potential antithyroid properties of thioglycolurils and fused azolo-1,2,4-triazines

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

Abstract

The protolytic properties and reactions with molecular iodine and blood serum proteins of 5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione and (R)-1,3-dialkyl-4-[(2-hydroxybenzylidene)amino]-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones were studied. These compounds exhibit different chemical reactivities towards molecular iodine. The binding constants between these compounds and serum albumin attest to a considerable protein affinity of the compounds. The properties of the thiones make them promising as antithyroid agents.

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.

Similar content being viewed by others

References

  1. V. L. Rusinov, O. N. Chupakhin, S. L. Deev, T. S. Shestakova, E. N. Ulomskii, L. I. Rusinova, O. I. Kiselev, E. G. Deeva, Russ. Chem. Bull., 2010, 59, 136; DOI: https://doi.org/10.1007/s11172-010-0056-9.

    Article  CAS  Google Scholar 

  2. V. L. Rusinov, V. N. Charushin, O. N. Chupakhin, Russ. Chem. Bull., 2018, 67, 573; DOI: https://doi.org/10.1007/s11172-018-2113-8.

    Article  CAS  Google Scholar 

  3. V. L. Rusinov, E. N. Ulomsky, O. N. Chupakhin, V. N. Charushin, Russ. Chem. Bull., 2008, 57, 985; DOI: https://doi.org/10.1007/s11172-008-0130-8.

    Article  CAS  Google Scholar 

  4. F. El-Mariah, M. Hosny, A. Deeb, Phosphorus, Sulfur, Silicon, Relat. Elem., 2006, 181, 2505; DOI: https://doi.org/10.1080/10426500600754786.

    Article  CAS  Google Scholar 

  5. G. A. Gazieva, L. V. Anikina, S. A. Pukhov, T. B. Karpova, Yu. V. Nelyubina, A. N. Kravchenko, Mol. Divers., 2016, 20, 837; DOI: https://doi.org/10.1007/s11030-016-9671-1.

    Article  CAS  Google Scholar 

  6. G. A. Gazieva, L. V. Anikina, T. V. Nechaeva, S. A. Pukhov, T. B. Karpova, S. V. Popkov, Yu. V. Nelyubina, N. G. Kolotyrkina, A. N. Kravchenko, Eur. J. Med. Chem., 2017, 140, 141; DOI: https://doi.org/10.1016/j.ejmech.2017.09.009.

    Article  CAS  Google Scholar 

  7. G. A. Gazieva, T. V. Nechaeva, N. N. Kostikova, N. V. Sigay, S. A. Serkov, S. V. Popkov, Russ. Chem. Bull., 2018, 67, 1059; DOI: https://doi.org/10.1007/s11172-018-2180-x.

    Article  CAS  Google Scholar 

  8. G. A. Gazieva, Yu. B. Vikharev, L. V. Anikina, T. B. Karpova, A. N. Kravchenko, E. A. Permyakov, I. V. Svitanko, Mendeleev Commun., 2013, 23, 202; DOI: https://doi.org/10.1016/j.mencom.2013.07.007.

    Article  CAS  Google Scholar 

  9. C. Laurence, M. J. El Ghomari, M. Berthelot, J. Chem. Soc., Perkin Trans. 2, 1998, 1163; DOI: https://doi.org/10.1039/A800902C.

    Article  Google Scholar 

  10. C. Laurence, M. J. El Ghomari, M. Lucon, J. Chem. Soc., Perkin Trans. 2, 1998, 1159; DOI: https://doi.org/10.1039/A803002B.

    Article  Google Scholar 

  11. D. Manna, G. Roy, G. Mugesh, Acc. Chem. Res., 2013, 46, 2706; DOI: https://doi.org/10.1021/ar4001229.

    Article  CAS  Google Scholar 

  12. A. Nagasaka, H. Hidaka, J. Clin. Endocrinol. Metab., 1976, 43, 152; DOI: https://doi.org/10.1210/jcem-43-1-152.

    Article  CAS  Google Scholar 

  13. M. S. Chernov’yants, N. V. Aleshina, Z. A. Starikova, E. N. Sul’zhenko, Russ. Chem. Bull., 2010, 59, 1797; DOI: https://doi.org/10.1007/s11172-010-0315-9.

    Article  Google Scholar 

  14. W. W. du Mont, G. Mugesh, C. Wismach, P. G. Jones, Angew. Chem. (Int. Ed. Engl.), 2001, 40, 2486; DOI: https://doi.org/10.1002/1521-3773(20010702)40:13<2486:AID-ANIE2486>3.0.CO;2-N.

    Article  CAS  Google Scholar 

  15. M. S. Chernov’yants, I. V. Burykin, N. E. Erofeev, J. Anal. Chem., 2013, 68, 592; DOI: https://doi.org/10.7868/S0044450213060042.

    Google Scholar 

  16. V. A. Ivolgina, M. S. Chernov’yants, L. D. Popov, V. V. Suslonov, N. V. Lyanguzov, N. A. Avtushenko, J. Mol. Struct., 2019, 1180, 629; DOI: https://doi.org/10.1016/j.molstruc.2018.12.043.

    Article  CAS  Google Scholar 

  17. V. A. Ivolgina, M. S. Chernov’yants, Spectrochim. Acta, Part A, 2018, 199, 315; DOI: https://doi.org/10.1016/j.saa.2018.03.069.

    Article  CAS  Google Scholar 

  18. K. P. Bhabak, D. Bhowmick, J. Mol. Struct., 2012, 1022, 16; DOI: https://doi.org/10.1016/j.molstruc.2012.05.005.

    Article  CAS  Google Scholar 

  19. J. Buxeraud, A. C. Absil, J. Claude, C. Raby, G. Catanzano, C. Beck, Eur. J. Med. Chem., 1985, 20, 43.

    CAS  Google Scholar 

  20. L. D. Popov, G. A. Gazieva, A. N. Kravchenko, Yu. N. Tkachenko, O. I. Askalepova, S. I. Levchenkov, T. B. Karpova, Yu. P. Tupolova, V. A. Kogan, Russ. J. Gen. Chem., 2015, 85, 92; DOI: https://doi.org/10.1134/S1070363215010168.

    Article  CAS  Google Scholar 

  21. M. S. Chernov’yants, A. O. Dolinkin, A. V. Chernyshov, E.V. Khohlov, E. G. Golovanova, J. Pharm. Sci., 2010, 99, 1567; DOI: https://doi.org/10.1002/jps.21915.

    Article  Google Scholar 

  22. G. A. Gazieva, S. V. Vasilevskii, P. A. Belyakov, Yu. V. Nelyubina, E. D. Lubuzh, A. N. Kravchenko, Mendeleev Commun., 2010, 20, 285; DOI: https://doi.org/10.1016/j.mencom.2010.09.016.

    Article  CAS  Google Scholar 

  23. G. A. Gazieva, P. A. Poluboyarov, L. D. Popov, N. G. Kolotyrkina, A. N. Kravchenko, N. N. Makhova, Synthesis, 2012, 44, 3366; DOI: https://doi.org/10.1055/s-0032-1317194.

    Article  CAS  Google Scholar 

  24. G. A. Gazieva, Yu. V. Nelyubina, A. N. Kravchenko, A. S. Sigachev, I. V. Glukhov, M. I. Struchkova, K. A. Lyssenko, N. N. Makhova, Russ. Chem. Bull., 2009, 58, 1945; DOI: https://doi.org/10.1007/s11172-009-0266-1.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. A. Ivolgina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2215—2221, November, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ivolgina, V.A., Popov, L.D., Gazieva, G.A. et al. Protolytic and potential antithyroid properties of thioglycolurils and fused azolo-1,2,4-triazines. Russ Chem Bull 69, 2215–2221 (2020). https://doi.org/10.1007/s11172-020-3024-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-3024-z

Key words

Navigation