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Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity.

ABSTRACT: Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon-carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus.

SUBMITTER: Kalyaev MV

PROVIDER: S-EPMC9325161 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity.

Kalyaev Mikhail V MV Ryabukhin Dmitry S DS Borisova Marina A MA Ivanov Alexander Yu AY Boyarskaya Irina A IA Borovkova Kristina E KE Nikiforova Lia R LR Salmova Julia V JV Ul'yanovskii Nikolay V NV Kosyakov Dmitry S DS Vasilyev Aleksander V AV

Molecules (Basel, Switzerland) 20220719 14

Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon-carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good ...[more]

PMID: 35889484

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