Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives,and Study of Their Antimicrobial Activity |
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Authors: | Mikhail V. Kalyaev,Dmitry S. Ryabukhin,Marina A. Borisova,Alexander Yu. Ivanov,Irina A. Boyarskaya,Kristina E. Borovkova,Lia R. Nikiforova,Julia V. Salmova,Nikolay V. Ul’ yanovskii,Dmitry S. Kosyakov,Aleksander V. Vasilyev |
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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. |
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Keywords: | furans, Friedel– Crafts reaction, carbocations, superelectrophilic activation, antibacterial activity |
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