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A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives
Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9733071/ https://www.ncbi.nlm.nih.gov/pubmed/36482476 http://dx.doi.org/10.1186/s13065-022-00902-1 |
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author | Gill, Muhammad Shoaib Ali Azzman, Nursyuhada Hassan, Sharifah Syed Shah, Syed Adnan Ali Ahemad, Nafees |
author_facet | Gill, Muhammad Shoaib Ali Azzman, Nursyuhada Hassan, Sharifah Syed Shah, Syed Adnan Ali Ahemad, Nafees |
author_sort | Gill, Muhammad Shoaib Ali |
collection | PubMed |
description | Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00902-1. |
format | Online Article Text |
id | pubmed-9733071 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-97330712022-12-10 A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives Gill, Muhammad Shoaib Ali Azzman, Nursyuhada Hassan, Sharifah Syed Shah, Syed Adnan Ali Ahemad, Nafees BMC Chem Research Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00902-1. Springer International Publishing 2022-12-08 /pmc/articles/PMC9733071/ /pubmed/36482476 http://dx.doi.org/10.1186/s13065-022-00902-1 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Gill, Muhammad Shoaib Ali Azzman, Nursyuhada Hassan, Sharifah Syed Shah, Syed Adnan Ali Ahemad, Nafees A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title | A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title_full | A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title_fullStr | A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title_full_unstemmed | A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title_short | A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
title_sort | green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives |
topic | Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9733071/ https://www.ncbi.nlm.nih.gov/pubmed/36482476 http://dx.doi.org/10.1186/s13065-022-00902-1 |
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