Skip to main content
SpringerLink
Log in

Chemoselective aminomethylation of quinopimaric acid

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

Abstract

In the development of research on studying the reactivity of quinopimaric acid, aminomethylation proceeding chemoselectively at position 3 of the carbon backbone was carried out.

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

References

  1. L. A. Baltina, R. M. Kondratenko, L. A. Baltina,Jr., O. A. Plyasunova, A. G. Pokrovskii, G. A. Tolstikov, Pharm. Chem. J. (Engl. Transl.), 2009, 43, 539–548; DOI: https://doi.org/10.1007/s11094-010-0348-2.

    Article  CAS  Google Scholar 

  2. A. V. Shernyukov, N. F. Salakhutdinov, G. A. Tolstikov, Russ. Chem. Bull., 2013, 62, 878–895; DOI: https://doi.org/10.1007/s11172-013-0120-3.

    Article  CAS  Google Scholar 

  3. E. E. Shul’ts, G. A. Tolstikov, Russ. Chem. Bull., 2013, 62, 605–621; DOI: https://doi.org/10.1007/s11172-013-0083-4.

    Article  Google Scholar 

  4. I. V. Nechepurenko, N. F. Salakhutdinov, G. A. Tolstikov, Khimiya v Interesakh Ustoichivogo Razvitiya [Chemistry in Interests of Stable Development], 2010, 18, 1–23 (in Russian).

    CAS  Google Scholar 

  5. G. A. Tolstikov, T. G. Tolstikova, E. E. Shul’ts, S. E. Tolstikov, M. V. Khvostov, Smolyanye Kisloty Khvoinykh Rossii. Khimiya, Farmakologiya [Resin Acids of Conifers in Russia. Chemistry, Pharmacology], Geo, Novosibirsk, 2011, 391 pp. (in Russian).

    Google Scholar 

  6. O. B. Kazakova, G. A. Tolstikov, Khimiya v Interesakh Ustoichivogo Razvitiya [Chemistry in Interests of Stable Development], 2008, 16, 727–730 (in Russian).

    CAS  Google Scholar 

  7. E. E. Shul’ts, V. A. Raldugin, K. P. Volcho, N. F. Salakhutdinov, G. A. Tolstikov, Russ. Chem. Rev., 2007, 76, 655–671; DOI: https://doi.org/10.1070/RC2007v076n07ABEH003717].

    Article  Google Scholar 

  8. A. G. Tolstikov, T. B. Khlebnikova, O. V. Tolstikova, G. A. Tolstikov, Russ. Chem. Rev., 2003, 72, 803–822; DOI: https://doi.org/10.1070/RC2003v072n09ABEH000822.

    Article  CAS  Google Scholar 

  9. I. V. Il’ina, D. V. Korchagina, E. A. Morozova, T. G. Tolstikova, K. P. Volcho, N. F. Salakhutdinov, Russ. Chem. Bull., 2022, 71, 2482–2488; DOI: https://doi.org/10.1007/s11172-022-3677-x.

    Article  Google Scholar 

  10. G. A. Tolstikov, V. M. Potapov, Izv. Akad. Nauk KazSSR. Ser. Khim. [Bull. Acad. Sci. Kazakh SSR, Ser. Chem.], 1969, 2, 43–48 (in Russian).

    Google Scholar 

  11. I. E. Smirnova, O. B. Kazakova, A. Loesche, S. Hoenke, R. Csuk, Med. Chem. Res., 2020, 29, 1478–1485; DOI: https://doi.org/10.1007/s00044-020-02566-9.

    Article  CAS  Google Scholar 

  12. Pat. RU 2472787 C1, 2013 (in Russian).

  13. O. B. Kazakova, E. V. Tret’yakova, I. E. Smirnova, L. V. Spirikhin, G. A. Tolstikov, I. V. Chudov, G. V. Bazekin, A. F. Ismagilova, Russ. J. Bioorg. Chem., 2010, 36, 257–262; DOI: https://doi.org/10.1134/S1068162010020160.

    Article  CAS  Google Scholar 

  14. O. B. Flekhter, E. V. Tret’yakova, N. S. Makara, S. F. Gabdrakhmanova, N. Zh. Baschenko, F. Z. Galin, F. S. Zarudii, G. A. Tolstikov, Pharm. Chem. J., 2003, 37, 142–144; DOI: https://doi.org/10.1023/A:1024538715025.

    Article  CAS  Google Scholar 

  15. O. B. Flekhter, E. V. Tret’yakova, F. Z. Galin, L. T. Karachurina, L. V. Spirikhin, F. S. Zarudii, G. A. Tolstikov, Pharm. Chem. J., 2002, 36, 428–431; DOI: https://doi.org/10.1023/A:1021210627098.

    Article  CAS  Google Scholar 

  16. O. B. Flekhter, I. E. Smirnova, E. V. Tret’yakova, G. A. Tolstikov, O. V. Savinova, E. I. Boreko, Russ. J. Bioorg. Chem., 2009, 35, 385–390; DOI: https://doi.org/10.1134/S1068162009030157.

    Article  CAS  Google Scholar 

  17. E. V. Tretyakova, I. E. Smirnova, E. V. Salimova, V. N. Odinokov, Bioorg. Med. Chem., 2015, 23, 6543–6550; DOI: https://doi.org/10.1016/j.bmc.2015.09.006.

    Article  CAS  PubMed  Google Scholar 

  18. E. V. Tret’yakova, X. Ma, O. B. Kazakova, A. A. Shtro, G. D. Petukhova, A. M. Klabukov, D. S. Dyatlov, A. A. Smirnova, H. Xu, S. Xiao, Phytochem. Lett., 2022, 51, 91–96; DOI: https://doi.org/10.1016/j.phytol.2022.07.010.

    Article  PubMed  PubMed Central  Google Scholar 

  19. E. V. Tretyakova, X. Ma, O. B. Kazakova, A. A. Shtro, G. D. Petukhova, A. A. Smirnova, H. Xu, S. Xiao, Nat. Prod. Res., 2023, 37, 1954; DOI: https://doi.org/10.1080/14786419.2022.2112040.

    Article  CAS  PubMed  Google Scholar 

  20. I. E. Smirnova, E. V. Tret’yakova, D. S. Baev, O. B. Kazakova, Nat. Prod. Res., 2023, 37, 313–321; DOI: https://doi.org/10.1080/14786419.2021.1969566.

    Article  CAS  PubMed  Google Scholar 

  21. E. V. Tretyakova, E. V. Salimova, L. V. Parfenova, Nat. Prod. Res., 2022, 36, 79–86; DOI: https://doi.org/10.1080/14786419.2020.1762187.

    Article  CAS  PubMed  Google Scholar 

  22. E. V. Tret’yakova, I. E. Smirnova, O. B. Kazakova, G. A. Tolstikov, N. P. Yavorskaya, I. S. Golubeva, R. B. Pugacheva, G. N. Apryshko, V. V. Poroikov, Bioorg. Med. Chem., 2014, 22, 6481–6489; DOI: https://doi.org/10.1016/j.bmc.2014.09.030.

    Article  Google Scholar 

  23. E. V. Tret’yakova, E. V. Salimova, L. V. Parfenova, M. M. Yunusbaeva, L. U. Dzhemileva, V. V. D’yakonov, U. M. Dzhemilev, Anticancer Agents in Medicinal Chemistry, 2019, 19, 1172–1183; DOI: https://doi.org/10.2174/1871520619666190404100846.

    Article  Google Scholar 

  24. O. B. Kazakova, E. V. Tret’yakova, I. E. Smirnova, T. I. Nazyrov, O. S. Kukovinets, G. A. Tolstikov, K. Y. Suponitskii, Nat. Prod. Commun., 2013, 8, 293–296.

    CAS  PubMed  Google Scholar 

  25. I. E. Smirnova, O. B. Kazakova, E. V. Tret’yakova, G. A. Tolstikov, L. V. Spirikhin, Russ. J. Org. Chem. (Int. Ed.), 2011, 47, 1576–1580; DOI: https://doi.org/10.1134/S1070428011100228.

    Article  CAS  Google Scholar 

  26. I. E. Smirnova, O. B. Kazakova, E. V. Tret’yakova, A. N. Lobov, L. V. Spirikhin, G. A. Tolstikov, K. Y. Suponitskii, Russ. J. Org. Chem. (Int. Ed.), 2011, 47, 1385–1389; DOI: https://doi.org/10.1134/S1070428011090223.

    Article  CAS  Google Scholar 

  27. D. S. Dyatlov, L. R. Yarmukhametova, O. S. Kukovinets, E. V. Tret’yakova, Vestnik Bashkir. Univ. [Bull. Bashkir Univ.], 2021, 26, 373–377; DOI: https://doi.org/10.33184/bulletin-bsu-2021.2.17 (in Russian).

    Article  Google Scholar 

  28. E. V. Tret’yakova, L. R. Yarmukhametova, E. V. Salimova, O. S. Kukovinets, L. V. Parfenova, Chem. Heterocycl. Compd., 2020, 56, 1366–1369; DOI: https://doi.org/10.1007/s10593-020-02824-z.

    Article  Google Scholar 

  29. A. S. Aboraia, H. M. Abdel-Rahman, N. M. Mahfouz, M. A. El-Gendy, Bioorg. Med. Chem., 2006, 14, 1236–1246; DOI: https://doi.org/10.1016/j.bmc.2005.09.053.

    Article  CAS  PubMed  Google Scholar 

  30. M. Tramontini, L. Angiolini, Mannich-Bases, Chemistry and Uses, CRC, Boca Raton, FL, 1994, 289 pp.

    Google Scholar 

  31. M. Arend, B. Westermann, N. Risch. Angew. Chem., Int. Ed. Engl., 1998, 37, 1044–1070; DOI: https://doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E.

    Article  PubMed  Google Scholar 

  32. P. Borah, G. Borah, A.C. Nath, W. Latif, B. K. Banik, ChemistrySelect, 2023, 8, e202203758; DOI: https://doi.org/10.1002/slct.202203758.

    Article  CAS  Google Scholar 

  33. S. S. Raoof1, A. S. Sadiq, Iraqi J. Science, 2022, 63, 5086–5105; DOI: https://doi.org/10.24996/ijs.2022.63.12.1.

    Article  Google Scholar 

  34. E. V. Buravlev, O. G. Shevchenko, Russ. Chem. Bull., 2020, 69, 1971–1978; DOI: https://doi.org/10.1007/s11172-020-2987-0.

    Article  CAS  Google Scholar 

  35. I. A. Dvornikova, E. V. Buravlev, O. G. Shevchenko, I. Yu. Chukicheva, A. V. Kutchin, Russ. Chem. Bull., 2021, 70, 2185–2188; DOI: https://doi.org/10.1007/s11172-021-3330-0.

    Article  CAS  Google Scholar 

  36. I. Yu. Chukicheva, E. V. Buravlev, I. A. Dvornikova, I. V. Fedorova, V. V. Zarubaev, A. V. Slita, Ya. L. Esaulkova, A. V. Kutchin, Russ. Chem. Bull., 2022, 71, 2473–2481; DOI: https://doi.org/10.1007/s11172-022-3676-y.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. S. K. Raju, A. Settu, A. Thiyagarajan, D. Rama, Res. J. Biol. Pharm., 2023, 7, 1–15; DOI: https://doi.org/10.53022/oarjbp.2023.7.2.0015.

    Google Scholar 

  38. E. V. Tret’yakova, E. V. Salimova, L. V. Parfenova, V. N. Odinokov, Russ. J. Org. Chem. (Int. Ed.), 2016, 52, 1496–1502; DOI: https://doi.org/10.1134/S1070428016100201.

    Article  Google Scholar 

  39. E. Tret’yakova, I. Smirnova, O. Kazakova, H. T. T. Nguyen, A. Shevchenko, E. Sokolova, D. Babkov, A. Spasov, Int. J. Mol. Sci., 2022, 23, 13535; DOI: https://doi.org/10.3390/ijms232113535.

    Article  Google Scholar 

  40. A. A. Smirnova, E. V. Tret’yakova, O. B. Kazakova, Russ. J. Org. Chem. (Int. Ed.), 2022, 58, 1652–1655; DOI: https://doi.org/10.1134/S1070428022110148.

    Article  CAS  Google Scholar 

  41. G. A. Tolstikov, E. E. Shul’ts, T. Sh. Mukhametzyanova, I. P. Baikova, L. V. Spirikhin, Russ. J. Org. Chem. (Int. Ed.), 1993, 29, 110.

    Google Scholar 

  42. W. Herz, R. C. Blackstone, M. G. Nair, J. Org. Chem., 1967, 32, 2992–2998; DOI: https://doi.org/10.1021/jo01285a014.

    Article  CAS  Google Scholar 

  43. E. E. Shul’ts, D. S. Oleinikov, I. V. Nechepurenko, M. M. Shakirov, G. A. Tolstikov, Russ. J. Org. Chem., 2009, 45, 102–114; DOI: https://doi.org/10.1134/S1070428009010138.

    Article  Google Scholar 

Download references

Funding

This work was carried out in terms of the state assignment No. 1021062311392-9-1.4.1. 1H and 13C NMR spectra were recorded using the equipment of the Centers for Collective Use “Khimiya” and “Agidel” of the Ufa Federal Research Center of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    A. A. Smirnova & E. V. Tret’yakova

Authors
  1. A. A. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Tret’yakova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Tret’yakova.

Ethics declarations

Animal Testing and Ethics

No human or animal subjects were used in this research.

Conflict of Interests

The authors declare no competing interests.

Additional information

Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2404–2410, October, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smirnova, A.A., Tret’yakova, E.V. Chemoselective aminomethylation of quinopimaric acid. Russ Chem Bull 72, 2404–2410 (2023). https://doi.org/10.1007/s11172-023-4040-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4040-6

Key words

Search

Navigation