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A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities †
The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10058827/ https://www.ncbi.nlm.nih.gov/pubmed/36985452 http://dx.doi.org/10.3390/molecules28062479 |
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author | Zapol’skii, Viktor A. Kaul, Sandra Karge, Bianka Brönstrup, Mark Gjikaj, Mimoza Kaufmann, Dieter E. |
author_facet | Zapol’skii, Viktor A. Kaul, Sandra Karge, Bianka Brönstrup, Mark Gjikaj, Mimoza Kaufmann, Dieter E. |
author_sort | Zapol’skii, Viktor A. |
collection | PubMed |
description | The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the precursor. Due to the steric bulk and high electron density ring, the ring closure of benzo[h]quinolines takes place exclusively. Such highly substituted annelated pyridine systems can be modified in subsequent, selective reactions to build up new N-heterocycles with promising microbiological properties. The antibacterial and antiproliferative assays against four mammalian cell lines demonstrate that some of the sulfur-substituted benzo[h]quinoline analogs display potent phenotypic bioactivities in the single-digit micromolar range. |
format | Online Article Text |
id | pubmed-10058827 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100588272023-03-30 A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † Zapol’skii, Viktor A. Kaul, Sandra Karge, Bianka Brönstrup, Mark Gjikaj, Mimoza Kaufmann, Dieter E. Molecules Article The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the precursor. Due to the steric bulk and high electron density ring, the ring closure of benzo[h]quinolines takes place exclusively. Such highly substituted annelated pyridine systems can be modified in subsequent, selective reactions to build up new N-heterocycles with promising microbiological properties. The antibacterial and antiproliferative assays against four mammalian cell lines demonstrate that some of the sulfur-substituted benzo[h]quinoline analogs display potent phenotypic bioactivities in the single-digit micromolar range. MDPI 2023-03-08 /pmc/articles/PMC10058827/ /pubmed/36985452 http://dx.doi.org/10.3390/molecules28062479 Text en © 2023 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 | Article Zapol’skii, Viktor A. Kaul, Sandra Karge, Bianka Brönstrup, Mark Gjikaj, Mimoza Kaufmann, Dieter E. A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title | A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title_full | A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title_fullStr | A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title_full_unstemmed | A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title_short | A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities † |
title_sort | new way to 2,3,4-trisubstituted benzo[h]quinolines: synthesis, consecutive reactions and cellular activities † |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10058827/ https://www.ncbi.nlm.nih.gov/pubmed/36985452 http://dx.doi.org/10.3390/molecules28062479 |
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