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Synthesis and antimicrobial activity of new thiomonoterpene carboxylic acids

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Abstract

A series of new compounds containing monoterpenoid fragments, sulfide and carboxy groups was synthesized. The reaction of monoterpene thiols with bromoacetic acid and ethyl 2-bromo-2,2-difluoroacetate afforded new thiomonoterpene carboxylic acids in 80–96% and 56–80% yields, respectively. The synthesized compounds were studied for antimicrobial activity. Some structure–property interrelations were revealed, which depended on the monoterpene fragment structure and the presence of fluorine atoms in the carboxymethyl group.

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Funding

This work was financially supported by the Russian Science Foundation (Project No. 21-13-00245) and carried out using the equipment of the Center of Collective Usage (CCU) “Chemistry”, Institute of Chemistry of Komi Science Center of the Ural Branch of the Russian Academy of Sciences.

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167000, Syktyvkar, Russian Federation

    D. V. Sudarikov, E. V. Chashchina & S. A. Rubtsova

  2. Pitirim Sorokin Syktyvkar State University, 55 Octyabr’sky prosp., 167001, Syktyvkar, Russian Federation

    E. V. Chashchina

  3. Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    A. I. Kolesnikova, D. R. Baidamshina & A. R. Kayumov

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  1. D. V. Sudarikov
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  2. E. V. Chashchina
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  3. A. I. Kolesnikova
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  4. D. R. Baidamshina
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  5. A. R. Kayumov
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  6. S. A. Rubtsova
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Correspondence to D. V. Sudarikov.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii auk. Seriya Khimicheskaya, Vol. 73, No. 2, pp. 449–57, February, 2024.

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Sudarikov, D.V., Chashchina, E.V., Kolesnikova, A.I. et al. Synthesis and antimicrobial activity of new thiomonoterpene carboxylic acids. Russ Chem Bull 73, 449–457 (2024). https://doi.org/10.1007/s11172-024-4152-7

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