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Synthesis and antiviral activity of novel 3-substituted pyrazolinium salts

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Chemistry of Heterocyclic Compounds Aims and scope

For the first time, convenient methods for the preparation of pyrazoline N-alkylidene salts based on terpene (camphor, camphorquinone, carvone) ketones, cage (adamantanone and norcamphor) ketones, and natural aldehydes (carvone and myrtenal) allowing the isolation of stable pyrazolinium salts in individual form were proposed. Optimization of the conditions for the synthesis of the target products was carried out. The antiviral activity of the synthesized salts was studied; among the tested compounds 1-bornylidene-3-phenylpyrazolinium tetrafluoroborate (IC50 6.2 μM, SI 107) exhibited the greatest activity against influenza A/Puerto Rico/8/34 (H1N1) virus.

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Figure 1.
Scheme 1.
Scheme 2.

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Notes

  1. The numbering of the atoms in the bornyl fragment in the description of the spectra is carried out by analogy with other cyclic ketones: the atom bonded to the pyrazoline ring is designated as C-1.

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Authors and Affiliations

  1. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Nikolai O. Vorozhtsov, Vitalii A. Roznyatovskii, Boris N. Tarasevich, Yuliya A. Kozlovskaya, Aneliya I. Petkova & Elena K. Beloglazkina

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Olga I. Yarovaya & Nariman F. Salakhutdinov

  3. Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St., Saint Petersburg, 197101, Russia

    Aleksander V. Slita, Ekaterina O. Sinegubova & Vladimir V. Zarubaev

Authors
  1. Nikolai O. Vorozhtsov
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  2. Olga I. Yarovaya
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  3. Vitalii A. Roznyatovskii
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  4. Boris N. Tarasevich
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  5. Yuliya A. Kozlovskaya
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  6. Aneliya I. Petkova
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  7. Aleksander V. Slita
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  8. Ekaterina O. Sinegubova
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  9. Vladimir V. Zarubaev
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  10. Nariman F. Salakhutdinov
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  11. Elena K. Beloglazkina
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Corresponding author

Correspondence to Nikolai O. Vorozhtsov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(4), 432–441

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Vorozhtsov, N.O., Yarovaya, O.I., Roznyatovskii, V.A. et al. Synthesis and antiviral activity of novel 3-substituted pyrazolinium salts. Chem Heterocycl Comp 57, 432–441 (2021). https://doi.org/10.1007/s10593-021-02921-7

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  • DOI: https://doi.org/10.1007/s10593-021-02921-7

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