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Synthesis of cyclic D-(+)-camphoric acid imides and study of their antiviral activity

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Chemistry of Heterocyclic Compounds Aims and scope

Several D-(+)-camphoric acid imides, not previously described in the literature, were synthesized with good yields. The synthesis of previously known imides was improved. The cytotoxicity and antiviral activity of all synthesized imides were studied.

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References

  1. Salakhutdinov, N. F.; Volcho, K. P.; Yarovaya, O. I. Pure Appl. Chem. 2017, 89, 1105.

    Article  CAS  Google Scholar 

  2. Sokolova, A. S.; Yarovaya, О. I.; Shtro, A. A.; Borisova, M. S.; Morozova, E. A.; Tolstikova, T. G.; Zarubaev, V. V; Salakhutdinov, N. F. Chem. Heterocycl. Compd. 2017, 53, 371. [Khim. Geterotsikl. Soedin. 2017, 53, 371.]

  3. Sokolova, A. S.; Yarovaya, O. I.; Shernyukov, A. V.; Gatilov, Y. V.; Razumova, Y. V.; Zarubaev, V. V.; Tretiak, T. S.; Pokrovsky, A. G.; Kiselev, O. I.; Salakhutdinov, N. F. Eur. J. Med. Chem. 2015, 105, 263.

    Article  CAS  Google Scholar 

  4. Sokolova, A. S.; Yarovaya, O. I.; Bormotov, N. I.; Shishkina, L. N.; Salakhutdinov, N. F. MedChemComm 2018, 9, 1746.

    Article  CAS  Google Scholar 

  5. Chernyshov, V. V.; Yarovaya, O. I.; Fadeev, D. S.; Gatilov, Y. V.; Esaulkova, Y. L.; Muryleva, A. S.; Sinegubova, K. O.; Zarubaev, V. V.; Salakhutdinov, N. F. Mol. Diversity 2020, 24, 61.

    Article  CAS  Google Scholar 

  6. Firstova, A. A.; Kofanov, E. R.; Zakshevskaya, V. M.; Kovaleva, M. I. Russ. J. Bioorg. Chem. 2019, 45, 204. [Bioorg. Khim. 2019, 45, 430.]

  7. Xu, M.; Wang, Y.; Yang, F.; Wu, C.; Wang, Z.; Ye, B.; Jiang, X.; Zhao, Q.; Li, J.; Liu, Y.; Zhang, J.; Tian, G.; He, Y.; Shen, J.; Jiang, H. Eur. J. Med. Chem. 2018, 145, 74.

    Article  Google Scholar 

  8. Köse, A.; Kaya, M.; Kishalı, N. H.; Akdemir, A.; Şahin, E.; Kara, Y.; Şanlı-Mohamed, G. Bioorg. Chem. 2020, 94, 103421.

    Article  Google Scholar 

  9. Chen, H.; Song, W.; Huang, S. Chem. Heterocycl. Compd. 2006, 42, 726. [Khim. Geterotsikl. Soedin. 2006, 832.]

  10. Novakov, I. A.; Sheikin, D. S.; Chapurkin, V. V.; Nawrozkij, M. B.; Babushkin, A. S.; Kuznetsov, Y. P.; Ruchko, E. A.; Kachala, V. V.; Maryshev, A. Yu.; Schols, D. Chem. Heterocycl. Compd. 2020, 56, 67. [Khim. Geterotsikl. Soedin. 2020, 56, 67.]

  11. El-Etrawy, A. Sh.; Abdel-Rahman, A. A.-H. Chem. Heterocycl. Compd. 2010, 46, 1105. [Khim. Geterotsikl. Soedin. 2010, 1372.]

  12. Komissarov, I. V.; Dulenko, V. I.; Voshchula, V. N.; Kharin, N. A.; Naletov, S. V.; Mamonov, A. B. Pharm. Chem. J. 1994, 28, 638. [Khim.-Farm. Zh. 1994, 28(9), 27.]

  13. Takeda, K.; Tsuboyama, K.; Suzuki, A.; Ogura, H. Chem. Pharm. Bull. 1985, 33, 2545.

    Article  CAS  Google Scholar 

  14. Wanner, K. T. J. Chem. Inf. Model. 1988, 321, 353.

    CAS  Google Scholar 

  15. Bell, K. H. Aust. J. Chem. 1981, 34, 665.

    Article  CAS  Google Scholar 

  16. Rice, L. M.; Grogan, C. H. Hypotens. Agents 1957, 185.

  17. Merzlikin, S. I.; Sal’nikova, S. I.; Yaremenko, F. G. Pharm. Chem. J. 2001, 35, 139.

    Article  CAS  Google Scholar 

  18. Eagles, J. B.; Hitchcock, S. R. Tetrahedron: Asymmetry 2010, 21, 519.

    Article  CAS  Google Scholar 

  19. Moloney, M. G.; Paul, D. R.; Thompson, R. M.; Wright, E. Tetrahedron: Asymmetry 1996, 7, 2551.

    Article  CAS  Google Scholar 

  20. Hintermann, L.; Broggini, D.; Togni, A. Helv. Chim. Acta 2002, 85, 1597.

    Article  CAS  Google Scholar 

  21. Boeckman, R. K., Jr.; Miller, Y.; Savage, D.; Summerton, J. E. Tetrahedron Lett. 2011, 52, 2243.

    Article  CAS  Google Scholar 

  22. Kazemi, F.; Kiasat, A. R.; Mombaini, B. Synth. Commun. 2007, 37, 3219.

    Article  CAS  Google Scholar 

  23. Kononova, A. A.; Sokolova, A. S.; Cheresiz, S. V.; Yarovaya, O. I.; Nikitina, R. A.; Chepurnov, A. A.; Pokrovsky, A. G.; Salakhutdinov, N. F. MedChemComm 2017, 8, 2233.

    Article  CAS  Google Scholar 

  24. Gwon, Y.-D.; Strand, M.; Lindqvist, R.; Nilsson, E.; Saleeb, M.; Elofsson, M.; Överby, A. K.; Evander, M. Viruses 2020, 12, 351.

    Article  CAS  Google Scholar 

  25. Singh, I. P.; Gupta, S.; Kumar, S. Med. Chem. 2020, 16, 4.

    Article  CAS  Google Scholar 

  26. Saudi, M.; Zmurko, J.; Kaptein, S.; Rozenski, J.; Neyts, J.; Van Aerschot, A. Eur. J. Med. Chem. 2014, 87, 529.

    Article  CAS  Google Scholar 

  27. Spizzichino, S.; Mattedi, G.; Lauder, K.; Valle, C.; Aouadi, W.; Canard, B.; Decroly, E.; Kaptein, S. J. F.; Neyts, J.; Graham, C.; Sule, Z.; Barlow, D. J.; Silvestri, R.; Castagnolo, D. ChemMedChem 2020, 15, 385.

    Article  CAS  Google Scholar 

  28. Delang, L.; Li, C.; Tas, A.; Quérat, G.; Albulescu, I. C.; De Burghgraeve, T.; Segura Guerrero, N. A.; Gigante, A.; Piorkowski, G.; Decroly, E.; Jochmans, D.; Canard, B.; Snijder, E. J.; Pérez-Pérez, M. J.; van Hemert, M. J.; Coutard, B.; Leyssen, P.; Neyts, J. Sci. Rep. 2016, 6, 31819.

    Article  CAS  Google Scholar 

  29. Lacroix, C.; Querol-Audí, J.; Roche, M.; Franco, D.; Froeyen, M.; Guerra, P.; Terme, T.; Vanelle, P.; Verdaguer, N.; Neyts, J.; Leyssen, P. J. Antimicrob. Chemother. 2014, 69, 2723.

    Article  CAS  Google Scholar 

  30. Tănase, C. I.; Drăghici, C.; Hanganu, A.; Pintilie, L.; Maganu, M.; Volobueva, A.; Sinegubova, E.; Zarubaev, V. V.; Neyts, J.; Jochmans, D.; Slita, A. V. Molecules 2019, 24, 2446.

    Article  Google Scholar 

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The authors would like to express their gratitude to the Collective Use Chemical Service Center of the Siberian Branch of Russian Academy of Sciences, for the obtained spectra and analytical data, as well as Dr. D. S. Fadeev for the obtained NMR spectra data. The authors also would like to thank Prof. J. Neyts, Dr. D. Jochmans, and C. Collard (Rega Institute for Medical Research, KU Leuven) for the obtained data on the antiviral activity.

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Correspondence to Vladimir V. Chernyshov.

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Supplementary information file containing 1H and 13C NMR spectra, IR spectra, and HRMS of all synthesized compounds is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(6), 763–768

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Chernyshov, V.V., Yarovaya, O.I., Peshkov, R.Y. et al. Synthesis of cyclic D-(+)-camphoric acid imides and study of their antiviral activity. Chem Heterocycl Comp 56, 763–768 (2020). https://doi.org/10.1007/s10593-020-02728-y

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  • DOI: https://doi.org/10.1007/s10593-020-02728-y

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