Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity
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
Affiliations
Mikhail V. Kalyaev
Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky Per., 5, 194021 Saint Petersburg, Russia
Dmitry S. Ryabukhin
Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky Per., 5, 194021 Saint Petersburg, Russia
Marina A. Borisova
Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky Per., 5, 194021 Saint Petersburg, Russia
Alexander Yu. Ivanov
Center for Magnetic Resonance, Research Park, Saint Petersburg State University, Universitetskiy Pr., 26, 198504 Saint Petersburg, Russia
Irina A. Boyarskaya
Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab., 7/9, 199034 Saint Petersburg, Russia
Kristina E. Borovkova
Research and Manufacturing Company «Home of Pharmacy», Zavodskaya St., 3-245, Kuz’molovskiy Settlement, 188663 Saint Petersburg, Russia
Lia R. Nikiforova
Research and Manufacturing Company «Home of Pharmacy», Zavodskaya St., 3-245, Kuz’molovskiy Settlement, 188663 Saint Petersburg, Russia
Julia V. Salmova
Research and Manufacturing Company «Home of Pharmacy», Zavodskaya St., 3-245, Kuz’molovskiy Settlement, 188663 Saint Petersburg, Russia
Nikolay V. Ul’yanovskii
Core Facility Center “Arktika”, Northern (Arctic) Federal University, Nab. Severnoy Dviny, 17, 163002 Arkhangelsk, Russia
Dmitry S. Kosyakov
Core Facility Center “Arktika”, Northern (Arctic) Federal University, Nab. Severnoy Dviny, 17, 163002 Arkhangelsk, Russia
Aleksander V. Vasilyev
Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky Per., 5, 194021 Saint Petersburg, Russia
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.
