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Fischer Reaction in the Synthesis of New Triterpene Indoles of the Fusidane Series

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Abstract

The Fischer reaction of 3,11-dioxo derivatives of fusidic acid and its esters with phenylhydrazine chemoselectively occurred at the 3-position with the formation of indole-fused fusidane triterpenoids. The reaction with 3-chlorophenylhydrazine under similar conditions afforded mixtures of isomeric 6- and 4-chloro derivatives at a ratio of 3:2. 2,4-Dinitrophenylhydrazine reacted with the same fusidane diketones to give the corresponding hydrazones at the 3-oxo group. Biological screening of the synthesized compounds revealed derivatives exhibiting a high antibacterial activity against methicillin-resistant Staphylococcus aureus with a minimum inhibitory concentration of ≤0.25 μg/mL.

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ACKNOWLEDGMENTS

The in vitro antimicrobial activity of compounds 1–20 was evaluated according to the program of the Community for Antimicrobial Drug Discovery (CO-ADD) under financial support by the Wellcome Trust (UK) and University of Queensland (Australia). The spectral studies were carried out at the Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed according to state assignment no. AAAA-A19-119022290012-3.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 450075, Ufa, Russia

    E. V. Salimova & L. V. Parfenova

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  1. E. V. Salimova
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  2. L. V. Parfenova
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Correspondence to E. V. Salimova.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 36–50 https://doi.org/10.31857/S0514749222010037.

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Salimova, E.V., Parfenova, L.V. Fischer Reaction in the Synthesis of New Triterpene Indoles of the Fusidane Series. Russ J Org Chem 58, 25–37 (2022). https://doi.org/10.1134/S1070428022010031

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