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Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers

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Abstract

The reaction of isoalantolactone with primary amines or piperazine proceeds under mild conditions with high stereoselectivity to give 11,13-isoalantolactone dimers connected by an alkyldiamine or piperazine linker. The reaction of isoalantolactone with propargylamine hydrochloride afforded the corresponding 13-propargylamino-11,13-dihydroisoalantolactone or 13-propargylamino-N-bis(11,13-dihydroisoalantolactone). The synthesized propargylamines showed high activity in the Cu-catalyzed cycloaddition with organic azides. The newly synthesized compounds with a bis-eudesman structure were found to exhibit antibacterial activity against strains of Staphylococcus aureus, Bacillus cereus, and Escherichia coli.

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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. 23-73-00077).

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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

    S. S. Patrushev, D. O. Vasil’eva & E. E. Shults

  2. Novosibirsk State University, 1 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    S. S. Patrushev

  3. Novosibirsk State Medical University, 52 Krasnyi prosp., 630091, Novosibirsk, Russian Federation

    L. G. Burova, E. A. Bondareva, L. N. Zakharova & A. N. Evstropov

Authors
  1. S. S. Patrushev
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  2. D. O. Vasil’eva
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  3. L. G. Burova
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  4. E. A. Bondareva
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  5. L. N. Zakharova
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  6. A. N. Evstropov
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  7. E. E. Shults
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Corresponding author

Correspondence to E. E. Shults.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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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. 2513–2524, October, 2023.

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Patrushev, S.S., Vasil’eva, D.O., Burova, L.G. et al. Synthesis and evaluation of antibacterial activity of bis-eudesmanolides connected by nitrogen-containing linkers. Russ Chem Bull 72, 2513–2524 (2023). https://doi.org/10.1007/s11172-023-4054-0

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  • DOI: https://doi.org/10.1007/s11172-023-4054-0

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