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Synthesis of (1S)-(+)-camphor-10-sulfonamides and evaluation of their anti-filovirus activity

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Abstract

A series of new (1S)-(+)-camphor-10-sulfonamides containing various substituents at the nitrogen atom were synthesized, and their antiviral properties against Ebola virus were evaluated using a vesicular stomatitis virus-based pseudovirus system. The reduction of the carbonyl group at the C(2) atom leads to a significant improvement in the antiviral efficacy, whereas the transformation into oxime results in the almost complete disappearance of antiviral activity. According to the evaluation of antiviral activity against natural Ebola virus, the lead compounds exhibit moderate inhibitory activity. Interactions of the lead compounds with the binding site of Ebola virus glycoprotein were studied by molecular modeling. A comparative analysis of the changes due to possible interactions of the synthesized ligands and known inhibitors with Ebola virus surface glycoprotein was carried out.

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Acknowledgements

We would like to acknowledge the staff of the Multi-Access Chemical Service Center of the N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences for spectral and analytical measurements.

Funding

This study was financially supported by the Russian Science Foundation (Project No. 22-73-00168).

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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. Akademika Lavrentieva, 630090, Novosibirsk, Russian Federation

    A. S. Sokolova, D. V. Baranova, O. I. Yarovaya, D. S. Baev, T. G. Tolstikova & N. F. Salakhutdinov

  2. State Research Center of Virology and Biotechnology “Vector”, Rospotrebnadzor, 630559, Koltsovo, Novosibirsk Region, Russian Federation

    A. V. Zybkina, E. D. Mordvinova, A. V. Zaykovskaya, D. N. Shcherbakov, O. V. Pyankov & R. A. Maksyutov

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  1. A. S. Sokolova
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  2. D. V. Baranova
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  3. O. I. Yarovaya
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  4. A. V. Zybkina
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  5. E. D. Mordvinova
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  6. A. V. Zaykovskaya
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  8. T. G. Tolstikova
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  9. D. N. Shcherbakov
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  11. R. A. Maksyutov
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  12. N. F. Salakhutdinov
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Corresponding author

Correspondence to A. S. Sokolova.

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This paper does not contain descriptions of studies on animals or humans.

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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. 2536–2547, October, 2023.

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Sokolova, A.S., Baranova, D.V., Yarovaya, O.I. et al. Synthesis of (1S)-(+)-camphor-10-sulfonamides and evaluation of their anti-filovirus activity. Russ Chem Bull 72, 2536–2547 (2023). https://doi.org/10.1007/s11172-023-4056-y

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  • DOI: https://doi.org/10.1007/s11172-023-4056-y

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