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

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...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2022, Vol.58 (1), p.25-37
Main Authors: Salimova, E. V., Parfenova, L. V.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Chemistry and Materials Science
Diketones
Esters
Hydrazones
Indoles
Organic Chemistry
Staphylococcus infections
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Summary: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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022010031