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

Pavel A. Sakharov,

^a Alexander N. Koronatov,

^a Alexander F. Khlebnikov,

^a Mikhail S. Novikov,^a Artem G. Glukharev,^a Elizaveta V. Rogacheva,^ab Liudmila A. Kraeva,^b Vladimir V. Sharoyko,^a Tatiana B. Tennikova

^a and Nikolai V. Rostovskii

*^a

Author affiliations

* Corresponding authors

^a Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., Saint Petersburg, Russia
E-mail: n.rostovskiy@spbu.ru

^b Pasteur Institute of Epidemiology and Microbiology, 14 Mira Street, Saint Petersburg, 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.

RSC Advances

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements