Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity
Mikhail V. Kalyaev, Dmitry S. Ryabukhin, M. A. Borisova, Alexander Yu. Ivanov, Irina А. Boyarskaya, Kristina E. Borovkova, Lia R. Nikiforova, Julia V. Salmova, N. V. Ul’yanovskii, Dmitry S. Kosyakov, Aleksander V. Vasilyev
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.