Non-natural 2 H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity

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

doi:10.1039/c9ra09345a

Non-natural 2 H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity

RSC Adv. 2019 Nov 21;9(65):37901-37905. doi: 10.1039/c9ra09345a. eCollection 2019 Nov 19.

Affiliations

¹ Institute of Chemistry, Saint Petersburg State University 7/9 Universitetskaya nab. Saint Petersburg 199034 Russia n.rostovskiy@spbu.ru.
² 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.