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Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of the primary amino group of hydrazones of (+)-camphor and (–)-fenchone with dihaloalkanes leading to the production of novel nitrogen-containing heterocyclic derivatives was investigated. It was shown that the reaction of hydrazones with 1,2-ethanedithiol in the presence of formaldehyde with the addition of 5% Sm(NO3)3·6H2O leads to the formation of compounds containing the 1,5,3-dithiazepane fragment. The method developed by us offers the advantage of the use of commercially available reagents and good yields in the synthesis of hydrazone heterocyclic derivatives. Studies of antiviral activity have shown that camphor-based N-heterocyclic compounds can be considered promising agents with activity against influenza A.

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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 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Kseniya S. Kovaleva, Olga I. Yarovaya, Yurii V. Gatilov & Nariman F. Salakhutdinov

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

    Aleksander V. Slita, Yana L. Esaulkova & Vladimir V. Zarubaev

  3. State Research Center of Virology and Biotechnology “Vector”, Federal Service for Surveillance on Consumer Rights Protection and Human Wellbeing, Koltsovo, 630559, Novosibirsk Oblast, Russia

    Nadezhda B. Rudometova, Nadezhda S. Shcherbakova & Dmitrii N. Shcherbakov

Authors
  1. Kseniya S. Kovaleva
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  2. Olga I. Yarovaya
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  3. Yurii V. Gatilov
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  4. Aleksander V. Slita
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  5. Yana L. Esaulkova
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  6. Vladimir V. Zarubaev
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  7. Nadezhda B. Rudometova
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  8. Nadezhda S. Shcherbakova
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  9. Dmitrii N. Shcherbakov
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  10. Nariman F. Salakhutdinov
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Corresponding author

Correspondence to Olga I. Yarovaya.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(4), 455–461

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Kovaleva, K.S., Yarovaya, O.I., Gatilov, Y.V. et al. Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone. Chem Heterocycl Comp 57, 455–461 (2021). https://doi.org/10.1007/s10593-021-02923-5

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  • DOI: https://doi.org/10.1007/s10593-021-02923-5

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