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Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity |
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| Authors: | Pavel A. Sakharov Alexander N. Koronatov Alexander F. Khlebnikov Mikhail S. Novikov Artem G. Glukharev Elizaveta V. Rogacheva Liudmila A. Kraeva Vladimir V. Sharoyko Tatiana B. Tennikova Nikolai V. Rostovskii |
| Affiliation: | Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., Saint Petersburg 199034 Russia.; Pasteur Institute of Epidemiology and Microbiology, 14 Mira Street, Saint Petersburg 197101 Russia |
| Abstract: | Non-natural 2H-azirine-2-carboxylic acids were obtained in high yields by FeCl2-catalyzed isomerization of 5-chloroisoxazoles to azirine-2-carbonyl chlorides followed by their hydrolysis. The 3-aryl- and 3-heteroaryl-substituted acids are stable during prolonged storage, exhibit antibacterial activity against ESKAPE pathogens and show a low level of cytotoxicity.A method for the synthesis of 2H-azirine-2-carboxylic acids with high antibacterial activity against ESKAPE pathogens and low cytotoxicity was developed. |
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