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Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation
In this work, we present the first synthesis of dispirooxindole-β-lactams employing optimized methodology of one-pot Staudinger ketene-imine cycloaddition with N-aryl-2-oxo-pyrrolidine-3-carboxylic acids as the ketene source. Spiroconjugation of indoline-2-one with β-lactams ring is considered to be...
| Autores principales: | , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
MDPI
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9223813/ https://www.ncbi.nlm.nih.gov/pubmed/35743110 http://dx.doi.org/10.3390/ijms23126666 |
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| author | Filatov, Vadim E. Iuzabchuk, Dmitrii A. Tafeenko, Viktor A. Grishin, Yuri K. Roznyatovsky, Vitaly A. Lukianov, Dmitrii A. Fedotova, Yulia A. Sukonnikov, Maxim A. Skvortsov, Dmitry A. Zyk, Nikolai V. Beloglazkina, Elena K. |
| author_facet | Filatov, Vadim E. Iuzabchuk, Dmitrii A. Tafeenko, Viktor A. Grishin, Yuri K. Roznyatovsky, Vitaly A. Lukianov, Dmitrii A. Fedotova, Yulia A. Sukonnikov, Maxim A. Skvortsov, Dmitry A. Zyk, Nikolai V. Beloglazkina, Elena K. |
| author_sort | Filatov, Vadim E. |
| collection | PubMed |
| description | In this work, we present the first synthesis of dispirooxindole-β-lactams employing optimized methodology of one-pot Staudinger ketene-imine cycloaddition with N-aryl-2-oxo-pyrrolidine-3-carboxylic acids as the ketene source. Spiroconjugation of indoline-2-one with β-lactams ring is considered to be able to provide stabilization and wide scope of functionalization to resulting scaffolds. The dispipooxindoles obtained demonstrated medium cytotoxicity in the MTT test on A549, MCF7, HEK293, and VA13 cell lines, and one of the compounds demonstrated antibacterial activity against E. coli strain LPTD. |
| format | Online Article Text |
| id | pubmed-9223813 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | MDPI |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-92238132022-06-24 Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation Filatov, Vadim E. Iuzabchuk, Dmitrii A. Tafeenko, Viktor A. Grishin, Yuri K. Roznyatovsky, Vitaly A. Lukianov, Dmitrii A. Fedotova, Yulia A. Sukonnikov, Maxim A. Skvortsov, Dmitry A. Zyk, Nikolai V. Beloglazkina, Elena K. Int J Mol Sci Communication In this work, we present the first synthesis of dispirooxindole-β-lactams employing optimized methodology of one-pot Staudinger ketene-imine cycloaddition with N-aryl-2-oxo-pyrrolidine-3-carboxylic acids as the ketene source. Spiroconjugation of indoline-2-one with β-lactams ring is considered to be able to provide stabilization and wide scope of functionalization to resulting scaffolds. The dispipooxindoles obtained demonstrated medium cytotoxicity in the MTT test on A549, MCF7, HEK293, and VA13 cell lines, and one of the compounds demonstrated antibacterial activity against E. coli strain LPTD. MDPI 2022-06-15 /pmc/articles/PMC9223813/ /pubmed/35743110 http://dx.doi.org/10.3390/ijms23126666 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Communication Filatov, Vadim E. Iuzabchuk, Dmitrii A. Tafeenko, Viktor A. Grishin, Yuri K. Roznyatovsky, Vitaly A. Lukianov, Dmitrii A. Fedotova, Yulia A. Sukonnikov, Maxim A. Skvortsov, Dmitry A. Zyk, Nikolai V. Beloglazkina, Elena K. Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title | Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title_full | Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title_fullStr | Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title_full_unstemmed | Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title_short | Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation |
| title_sort | dispirooxindole-β-lactams: synthesis via staudinger ketene-imine cycloaddition and biological evaluation |
| topic | Communication |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9223813/ https://www.ncbi.nlm.nih.gov/pubmed/35743110 http://dx.doi.org/10.3390/ijms23126666 |
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