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Reactions of highly electrophilic azolo[b]pyridines with polyphenols

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Abstract

Reactions of highly electrophilic azolo[b]pyridines with di- and triatomic phenols lead to products of 1,4-addition of C-nucleophiles to the pyridine cycle. It is found that another type of azoloazines, namely [1,2,4]triazolo[1,5-a]pyridines, are also capable to form adducts with polyphenols. Synthesized compounds containing simultaneously several pharmacophoric fragments are of interest as potential biologically active compounds.

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References

  1. M. McDonald, I. Mila, A. Scalbert, J. Agricult. Food Chem., 1996, 44, 599; DOI: https://doi.org/10.1021/jf950459q.

    Article  CAS  Google Scholar 

  2. Polyphenols: Properties, Recovery, and Application, Ed. C. M. Galanakis, Woodhead Publishing, 2018, 456 c.

  3. M. Funakoshi-Tago, M. Matsutaka, S. Hokimoto, K. Kobata, K. Tago, J. Funct. Foods, 2022, 90, 104980; DOI: https://doi.org/10.1016/j.jff.2022.104980.

    Article  CAS  Google Scholar 

  4. L. Zapór, Int. J. Occupational Safety and Ergonomics, 2004, 10, 319; DOI: https://doi.org/10.1080/10803548.2004.11076620.

    Article  Google Scholar 

  5. E. N. Ulomskiy, A. V. Ivanova, E. B. Gorbunov, I. L. Esaulkova, A. V. Slita, E. O. Sinegubova, E. K. Voinkov, R. A. Drokin, I. I. Butorin, E. R. Gazizullina, E. L. Gerasimova, V. V. Zarubaev, V. L. Rusinov, Bioorg. Med. Chem. Lett., 2020, 30, 127216; DOI: https://doi.org/10.1016/j.bmcl.2020.127216.

    Article  CAS  PubMed  Google Scholar 

  6. A. Ivanova, E. Gerasimova, E. Gazizullina, M. Borisova, R. Drokin, E. Gorbunov, E. Ulomskiy, V. Rusinov, Anal. Bioanal. Chem., 2020, 412, 5147; DOI: https://doi.org/10.1007/s00216-020-02466-2.

    Article  CAS  PubMed  Google Scholar 

  7. G. Micheletti, C. Boga, S. Cino, S. Bordoni, E. Chugunova, RSC Adv., 2018, 72, 41663; DOI: https://doi.org/10.1039/C8RA09460H.

    Article  Google Scholar 

  8. F. Terrier, M.-J. Pouet, J.-C. Halle, E. Kizilian, E. Buncel, J. Phys. Org. Chem., 1998, 11, 707; DOI: https://doi.org/10.1002/(SICI)1099-1395(1998100)11:10<707::AID-POC37>3.0.CO;2-V.

    Article  CAS  Google Scholar 

  9. A. M. Strarosotnikov, D. V. Shkaev, M. A. Bastrakov, I. V. Fedyanin, S. A. Shevelev, I. L. Dalinger, Beilstein J. Org. Chem., 2017, 13, 2854; DOI: https://doi.org/10.3762/bjoc.13.277.

    Article  Google Scholar 

  10. A. M. Starosotnikov, D. V. Shkaev, M. A. Bastrakov, I. V. Fedyanin, S. A. Shevelev, I. L. Dalinger, Mendeleev Commun., 2018, 28, 638; DOI: https://doi.org/10.1016/j.mencom.2018.11.025.

    Article  CAS  Google Scholar 

  11. M. A. Bastrakov, A. K. Fedorenko, A. M. Starosotnikov, Russ. Chem. Bull., 2020, 69, 394; DOI: https://doi.org/10.1007/s11172-020-2774-y.

    Article  CAS  Google Scholar 

  12. M. A. Bastrakov, A. K. Fedorenko, A. M. Starosotnikov, I. V. Fedyanin, V. A. Kokorekin, Molecules, 2020, 25, 2194; DOI: https://doi.org/10.3390/molecules25092194.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. A. M. Starosotnikov, K. V. Ilkov, M. A. Bastrakov, I. V. Fedyanin, V. A. Kokorekin, Chem. Heterocycl. Compd., 2020, 56, 92; DOI: https://doi.org/10.1007/s10593-020-02628-1.

    Article  CAS  Google Scholar 

  14. A. M. Starosotnikov, M. A. Bastrakov, V. A. Kokorekin, Russ. Chem. Bull., 2022, 71, 474; DOI: https://doi.org/10.1007/s11172-022-3435-0.

    Article  CAS  Google Scholar 

  15. V. V. Ivanova, A. K. Fedorenko, A. M. Starosotnikov, M. A. Bastrakov, Russ. Chem. Bull., 2022, 71, 1826; DOI: https://doi.org/10.1007/s11172-022-3596-x.

    Article  CAS  Google Scholar 

  16. V. K. Sharma, S. K. Singh, RSC Adv., 2017, 7, 2682; DOI:https://doi.org/10.1039/C6RA24823C.

    Article  CAS  Google Scholar 

  17. E. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem., 2014, 57, 10257; DOI: https://doi.org/10.1021/jm501100b.

    Article  CAS  PubMed  Google Scholar 

  18. A. M. Starosotnikov, M. A. Bastrakov, D. A. Knyazev, I. V. Fedyanin, V. V. Kachala, I. L. Dalinger, ChemistrySelect, 2019, 4, 1510; DOI: https://doi.org/10.1002/slct.201803068.

    Article  CAS  Google Scholar 

  19. K. S. Sharma, S. Kumari, R. P. Singh, Synthesis, 1981, 4, 316; DOI: https://doi.org/10.1055/s-1981-29435.

    Article  Google Scholar 

  20. M. A. Bastrakov, V. V. Nikol’skiy, A. M. Starosotnikov, I. V. Fedyanin, S. A. Shevelev, D. A. Knyazev, Tetrahedron, 2019, 75, 130659; DOI: https://doi.org/10.1016/j.tet.2019.130659.

    Article  Google Scholar 

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Correspondence to A. M. Starosotnikov.

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This work was performed under financial support of the Russian Science Foundation (Project No. 19-73-20259).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1219–1224, May, 2023.

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Starosotnikov, A.M., Bastrakov, M.A. & Kokorekin, V.A. Reactions of highly electrophilic azolo[b]pyridines with polyphenols. Russ Chem Bull 72, 1219–1224 (2023). https://doi.org/10.1007/s11172-023-3892-0

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  • DOI: https://doi.org/10.1007/s11172-023-3892-0

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