Skip to main content
Log in

Sterically shielded pyrrolidine nitroxides with 3-(4,5-dicarboxy-1H-1,2,3-triazol-1-yl)propyl substituent

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

Abstract

Water-soluble spin probes were obtained from reduction-resistant sterically shielded pyrrolidine nitroxides by forming a 4,5-dicarboxy-1H-1,2,3-triazole fragment in the side chain by the Huisgen reaction of the azido group with acetylenedicarboxylic acid ester followed by hydrolysis. For the synthesized radicals, the reduction rate constants by ascorbate and the partition coefficient in an octanol—water system were determined.

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. Nitroxides — Theory, Experiment and Applications, Ed. A. I. Kokorin, IntechOpen, London, 2012, 448 pp.; DOI: https://doi.org/10.5772/2887.

    Google Scholar 

  2. Nitroxides: Synthesis, Properties and Applications, Eds O. Ouari, D. Gigmes, Royal Society of Chemistry, London, 2021, 592 pp.

    Google Scholar 

  3. G. I. Likhtenshtein, J. Yamauchi, S. Nakatsuji, A. Smirnov, R. Tamura, Nitroxides. Applications in Chemistry, Biomedicine and Material Science, Wiley, New York, 2008, 441 pp.

    Book  Google Scholar 

  4. A. A. Efremov, A. S. Poryvaev, D. M. Polyukhov, S. A. Gromilov, M. V. Fedin, Russ. Chem. Bull., 2022, 71, 1422.

    Article  CAS  Google Scholar 

  5. J. T. Paletta, M. Pink, B. Foley, S. Rajca, A. Rajca, Org. Lett., 2012, 14, 5322–5325; DOI: https://doi.org/10.1021/o1302506f.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. S. S. Ovcherenko, O. A. Chinak, A. V. Chechushkov, S. A. Dobrynin, I. A. Kirilyuk, O. A. Krumkacheva, V. A. Richter, E. G. Bagryanskaya, Molecules, 2021, 26, 5442; DOI: https://doi.org/10.3390/molecules26185442.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. A. P. Jagtap, I. Krstic, N. C. Kunjir, R. Hänsel, T. F. Prisner, S. T. Sigurdsson, Free Radical Res., 2015, 49, 78–85; DOI: https://doi.org/10.3109/10715762.2014.979409.

    Article  CAS  Google Scholar 

  8. G. Karthikeyan, A. Bonucci, G. Casano, G. Gerbaud, S. Abel, V. Thomé, L. Kodjabachian, A. Magalon, B. Guigliarelli, V. Belle, O. Ouari, E. Mileo, Angew. Chem., Int. Ed., 2018, 57, 1366–1370; DOI: https://doi.org/10.1002/anie.201710184.

    Article  CAS  Google Scholar 

  9. S. Ketter, M. Dajka, O. Rogozhnikova, S. A. Dobrynin, V. M. Tormyshev, E. G. Bagryanskaya, B. Joseph, J. Magn. Reson. Open, 2022, 10–11, 100041; DOI: https://doi.org/10.1016/j.jmro.2022.100041.

    Article  Google Scholar 

  10. M. Emoto, F. Mito, T. Yamasaki, K. I. Yamada, H. Sato-Akaba, H. Hirata, H. Fujii, Free Radical Res., 2011, 45, 1325–1332; DOI: https://doi.org/10.3109/10715762.2011.618499.

    Article  CAS  Google Scholar 

  11. M. Soikkeli, M. I. Kettunen, R. Nivajärvi, V. Olsson, S. Rönkkö, J. P. Laakkonen, V. P. Lehto, J. Kavakka, S. Heikkinen, Contrast Media Mol. Imaging, 2019, 2019; DOI:https://doi.org/10.1155/2019/5629597

  12. L. Lampp, U. Morgenstern, K. Merzweiler, P. Imming, R. W. Seidel, J. Mol. Struct., 2019, 1182, 87–94; DOI: https://doi.org/10.1016/j.molstruc.2019.01.015.

    Article  CAS  Google Scholar 

  13. S. A. Dobrynin, Y. I. Glazachev, Y. V. Gatilov, E. I. Chernyak, G. E. Salnikov, I. A. Kirilyuk, J. Org. Chem., 2018, 83, 5392–5397; DOI: https://doi.org/10.1021/acs.joc.8b00085.

    Article  CAS  PubMed  Google Scholar 

  14. I. F. Zhurko, S. Dobrynin, A. A. Gorodetskii, Y. I. Glazachev, T. V. Rybalova, E. I. Chernyak, N. Asanbaeva, E. G. Bagryanskaya, I. A. Kirilyuk, Molecules, 2020, 25, 1–17; DOI: https://doi.org/10.3390/molecules25040845.

    Article  Google Scholar 

  15. S. A. Dobrynin, M. S. Usatov, I. F. Zhurko, D. A. Morozov, Y. F. Polienko, Y. I. Glazachev, D. A. Parkhomenko, M. A. Tyumentsev, Y. V. Gatilov, E. I. Chernyak, E. G. Bagryanskaya, I. A. Kirilyuk, Molecules, 2021, 26, 5761; DOI: https://doi.org/10.3390/molecules26195761.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. A. I. Taratayko, Yu. I. Glazachev, I. V. Eltsov, E. I. Chernyak, I. A. Kirilyuk, Molecules, 2022, 27, 1922; DOI: https://doi.org/10.3390/molecules27061922.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. J. F. W. Keana, in Spin Labelling II: Theory and Application, Ed. L. J. Berliner, Acad. Press, New York, 1979, pp. 115–172.

  18. K. Hideg, T. Kálai, C. P. Sár, J. Heterocycl. Chem., 2005, 42, 437; DOI: https://doi.org/10.1002/jhet.5570420311.

    Article  CAS  Google Scholar 

  19. A. Earla, E. D. Walter, R. Braslau, Free Radical Res., 2019, 53, 1084–1100; DOI:https://doi.org/10.1080/10715762.2019.1683171.

    Article  CAS  Google Scholar 

  20. K. Stolze, N. Udilova, T. Rosenau, A. Hofinger, H. Nohl, Biol. Chem., 2003, 384, 493–500; DOI: https://doi.org/10.1515/BC.2003.056.

    Article  CAS  PubMed  Google Scholar 

  21. Y. V. Khoroshunova, D. A. Morozov, A. I. Taratayko, P. D. Gladkikh, Y. I. Glazachev, I. A. Kirilyuk, Beilstein J. Org. Chem., 2019, 15, 2036–2042; DOI: https://doi.org/10.3762/bjoc.15.200.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. J. F. W. Keana, S. Pou, J. Org. Chem., 1989, 54, 2417–2420; DOI: https://doi.org/10.1021/jo00271a033.

    Article  CAS  Google Scholar 

  23. F. An, B. Maji, E. Min, A. R. Ofial, H. Mayr, J. Am. Chem. Soc., 2020, 142, 1526–1547; DOI: https://doi.org/10.1021/jacs.9b11877.

    Article  CAS  PubMed  Google Scholar 

  24. P. Merino, I. Delso, T. Tejero, F. Cardona, M. Marradi, E. Faggi, C. Parmeggiani, A. Goti, Eur. J. Org. Chem., 2008, 17, 2929–2947; DOI: https://doi.org/10.1002/ejoc.200800098.

    Article  Google Scholar 

  25. R. Ballini, G. Bosica, Eur. J. Org. Chem., 1998, 2, 355–357; DOI: https://doi.org/10.1002/(SICI)1099-0690(199802)1998:2<355::AID-EJOC355>3.0.CO;2-2.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. I. Taratayko.

Additional information

The authors are grateful to the stuff of the Chemical Research Center of the Collective Use at the Siberian Branch of the Russian Academy of Sciences for the spectral and analytical measurements.

This work was financially supported by the Russian Science Foundation (Project No. 21-73-00281).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Based on the materials of the All-Russian Conference “Markovnikov Readings: Organic Chemistry from Markovnikov to the Present Day” (WSOC 2022) (September 16–21, 2022, Sochi).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 7, pp. 1569–1575, July, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Trakhinina, S.Y., Taratayko, A.I., Glazachev, Y.I. et al. Sterically shielded pyrrolidine nitroxides with 3-(4,5-dicarboxy-1H-1,2,3-triazol-1-yl)propyl substituent. Russ Chem Bull 72, 1569–1575 (2023). https://doi.org/10.1007/s11172-023-3935-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3935-6

Key words

Navigation