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Synthesis and analgesic activity of alkyl-substituted octahydro-2H-chromenols

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Abstract

A series of new compounds with hydrogenated 2H-chromene framework was synthesized starting from aliphatic aldehydes and available p-menthane monoterpenoid (−)-isopulegol in the presence of montmorillonite K10. These compounds were formed as a pair of diastereoisomers, which were isolated individually using column chromatography. Some of the compounds obtained were found to exhibit high analgesic activity in in vivo tests.

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References

  1. W. F. Stewart, J. A. Ricci, E. Chee, D. Morganstein, R. Lipton, J. Am. Med. Ass., 2003, 290, 2443; DOI: https://doi.org/10.1001/jama.290.18.2443.

    Article  CAS  Google Scholar 

  2. N. D Moore, Acute Pain, 2009, 11, 129; DOI: https://doi.org/10.1016/j.acpain.2009.09.003.

    Article  CAS  Google Scholar 

  3. I. Melnikova, Nat. Rev. Drug. Discov., 2010, 9, 589; DOI: https://doi.org/10.1038/nrd3226.

    Article  CAS  Google Scholar 

  4. N. A. Shostak, A. A. Klimenko, N. A. Demidova, D. A. Anichkov, The Clinician, 2020, 14, 91; DOI: https://doi.org/10.17650/1818-8338-2020-14-1-2-91-99.

    Article  Google Scholar 

  5. D. A. Barrière, F. Boumezbeur, R. Dalmann, R. Cadeddu, D. Richard, J. Pinguet, L. Daulhac, Ph. Sarret, K. Whittingstall, M. Keller, S. Mériaux, A. Eschalier, Ch. Malle, Br. J. Pharmacol., 2020, 177, 1773; DOI: https://doi.org/10.1111/bph.14934.

    Article  Google Scholar 

  6. J. Woodcock, N. Engl. J. Med., 2009, 361, 2105; DOI: https://doi.org/10.1056/NEJMp0908913.

    Article  CAS  Google Scholar 

  7. J. Szychowski, J.-F. Truchon, Y. L. Bennani, J. Med. Chem., 2014, 57, 9292; DOI: https://doi.org/10.1021/jm500941m.

    Article  CAS  Google Scholar 

  8. M. E. Mironov, A. I. Poltanovich, T. V. Rybalova, M. P. Dolgikh, T. G. Tolstikova, E. E. Shults, Russ. Chem. Bull., 2020, 69, 537; DOI: https://doi.org/10.1007/s11172-020-2795-6.

    Article  CAS  Google Scholar 

  9. E. G. Chupakhin, M. Yu. Krasavin, Russ. Chem. Bull., 71, 2022, 443; DOI: https://doi.org/10.1007/s11172-022-3431-4.

    Article  CAS  Google Scholar 

  10. N. F. Salakhutdinov, K. P. Volcho, O. I. Yarovaya, Pure Appl. Chem., 2017, 89, 1105; DOI: https://doi.org/10.1515/pac-2017-0109.

    Article  CAS  Google Scholar 

  11. O. S. Patrusheva, K. P. Volcho, N. F. Salakhutdinov, Russ. Chem. Rev., 2018, 87, 771; DOI: https://doi.org/10.1070/RCR4810.

    Article  CAS  Google Scholar 

  12. O. I. Yarovaya, N. F. Salakhutdinov, Russ. Chem. Rev., 2021, 90, 488; DOI: https://doi.org/10.1070/RCR4969.

    Article  Google Scholar 

  13. O. S. Patrusheva, K. P. Volcho, N. F. Salakhutdinov, Russ. Chem. Rev., 2018, 87, 771; DOI: https://doi.org/10.1070/RCR4810.

    Article  CAS  Google Scholar 

  14. I. V. Il’ina, D. V. Korchagina, E. A. Morozova, T. G. Tolstikova, K. P. Volcho, N. F. Salakhutdinova, Russ. Chem. Bull., 2019, 68, 1061; DOI: https://doi.org/10.1007/s11172-019-2520-5.

    Article  Google Scholar 

  15. I. V. Il’ina, E. A. Morozova, D. V. Korchagina, K. P. Volcho, T. G. Tolstikova, N. F. Salakhutdinov, Lett. Drug Des. Discov., 2020, 17, 68; DOI: https://doi.org/10.2174/1570180816666181114131220.

    Article  Google Scholar 

  16. A. Pavlova, O. Patrusheva, I. Il’ina, K. Volcho, T. Tolstikova, N. Salakhutdinov, Lett. Drug Des. Discov., 2017, 14, 508; DOI: https://doi.org/10.2174/1570180813666161102142642.

    Article  CAS  Google Scholar 

  17. Sh. Slater, P. B. Lasonkar, S. Haider, M. J. Alqahtani, A. G. Chittiboyina, I. A. Khan, Tetrahedron Lett., 2018, 59, 807; DOI: https://doi.org/10.1016/j.tetlet.2018.01.040.

    Article  CAS  Google Scholar 

  18. N. S. Li-Zhulanov, I. V. Il’ina, A. Chicca, P. Schenker, O. S. Patrusheva, E. V. Nazimova, D. V. Korchagina, M. Krasavin, K. P. Volcho, N. F. Salakhutdinov, Med. Chem. Res., 2019, 28, 450; DOI: https://doi.org/10.1007/s00044-019-02294-9.

    Article  CAS  Google Scholar 

  19. I. V. Il’ina, O. S. Patrusheva, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov, Chem. Heterocycl. Compd., 2020, 56, 867; DOI: https://doi.org/10.1007/s10593-020-02743-z.

    Article  Google Scholar 

  20. I. Il’ina, A. Pavlova, D. Korchagina, O. Ardashov, T. Tolstikova, K. Volcho, N. Salakhutdinov, Med. Chem. Res., 2017, 26, 1415; DOI: https://doi.org/10.1007/s00044-017-1847-4.

    Article  Google Scholar 

  21. T. G. Tolstikova, A. V. Pavlova, E. A. Morozova, T. M. Khomenko, K. P. Volcho, N. F. Salakhutdinov, Lett. Drug Des. Discov., 2012, 9, 513; DOI: https://doi.org/10.2174/157018012800389296.

    Article  CAS  Google Scholar 

  22. M. V. Khvostov, S. A. Borisov, T. G. Tolstikova, A. V. Dushkin, B. D. Tsyrenova, Y. S. Chistyachenko, N. E. Polyakov, G. G. Dultseva, A. A. Onischuk, S. V. An’kov, Eur. J. Drug Metab. Ph., 2017, 42, 431; DOI: https://doi.org/10.1007/s13318-016-0357-y.

    Article  CAS  Google Scholar 

  23. N. B. Eddy, D. Leimbach, J. Pharm. Exp. Ther., 1953, 107, 385.

    CAS  Google Scholar 

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    I. V. Il’ina, D. V. Korchagina, E. A. Morozova, T. G. Tolstikova, K. P. Volcho & N. F. Salakhutdinov

Authors
  1. I. V. Il’ina
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  2. D. V. Korchagina
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  3. E. A. Morozova
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  4. T. G. Tolstikova
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  5. K. P. Volcho
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  6. N. F. Salakhutdinov
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Corresponding author

Correspondence to K. P. Volcho.

Additional information

This work was carried out within the framework of the Russian state assignment to the Pharmacological Research Laboratory of the N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (NIOC SB RAS) No. 1021051402785-4-1.4.1 and the Russian state assignment to the Laboratories of Physiologically Active Compounds of the NIOC SB RAS No. 1021051703312-0-1.4.1.

The authors of the work express their gratitude to the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for the spectral and analytical measurements.

The authors declare no competing interests.

Based on the materials of the V Russian Conference on Medicinal Chemistry with international participation “MedChem-Russia 2021” (May 16–19, 2022, Volgograd, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2482–2488, November, 2022.

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Il’ina, I.V., Korchagina, D.V., Morozova, E.A. et al. Synthesis and analgesic activity of alkyl-substituted octahydro-2H-chromenols. Russ Chem Bull 71, 2482–2488 (2022). https://doi.org/10.1007/s11172-022-3677-x

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  • DOI: https://doi.org/10.1007/s11172-022-3677-x

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