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

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

机译：非天然2H-叠氮基-2-羧酸：便利的合成方法和抗菌活性

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Non-natural 2 H -azirine-2-carboxylic acids were obtained in high yields by FeCl _(2) -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.

机译：通过FeCl_（2）催化5-氯异恶唑异构化为azirine-2-羰基氯，然后水解，可以高收率获得非天然2 H -azirine-2-羧酸。 3-芳基和3-杂芳基取代的酸在长时间存储期间稳定，对ESKAPE病原体表现出抗菌活性，并显示出低水平的细胞毒性。

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《RSC Advances》 |2019年第65期|共5页
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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;
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1. Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity [J] . RSC Advances . 2019,第65期

机译：非天然2H-氮杂胺-2-羧酸：有利的合成和抗微生物活性
2. Use of Non-Natural Amino Acids for the Design and Synthesis of a Selective, Cell-Permeable MALT1 Activity-Based Probe [J] . van de Plassche Merel A. T., ONeill Thomas J., Seeholzer Thomas, Journal of Medicinal Chemistry . 2020,第8期

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3. An engineered mutant,L307V of phenylalanine dehydrogenase from Bacillus sphaericus:high activity and stability in organic-aqueous solvent mixtures and utility for synthesis of non-natural L-amino acids [J] . Sihong Chen, Paul C.Engel Enzyme and Microbial Technology . 2007,第5期

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4. Towards SERS-based multiplexed monitoring of protease activity using non-natural aromatic amino acids [C] . Nina Turk, Hans Demol, Andre Skirtach, EOS Annual Meeting . 2020

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5. Non-natural mimics of lung surfactant proteins and antimicrobial peptides: Studies of biophysical, lipid-associated activities [D] . Dohm, Michelle Theresa 2009

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6. Cell-Free Protein Synthesis Using S30 Extracts from Escherichia coli RFzero Strains for Efficient Incorporation of Non-Natural Amino Acids into Proteins [O] . Jiro Adachi, Kazushige Katsura, Eiko Seki, 2019

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7. Synthesis of Non-Natural Amino Acids from N-(p-Tolylsulfonyl)-α,β-didehydroamino Acid Derivatives [O] . Paula M. T. Ferreira, Hernâni L. S. Maia, Luís S. Monteiro 2003

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8. Synthesis of Some N-Carboxy Methyl Amino Acid Esters and an Attempt to Prepare Di-(N-Carboxy Methyl Amino Acids Esters)-Sulphones for Possible Antimicrobial Activity [R] . Pasha, T. 1989

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

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