Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and...

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Autores principales: Mollova-Sapundzhieva, Yordanka, Angelov, Plamen, Georgiev, Danail, Yanev, Pavel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10682542/
https://www.ncbi.nlm.nih.gov/pubmed/38033452
http://dx.doi.org/10.3762/bjoc.19.132
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author Mollova-Sapundzhieva, Yordanka
Angelov, Plamen
Georgiev, Danail
Yanev, Pavel
author_facet Mollova-Sapundzhieva, Yordanka
Angelov, Plamen
Georgiev, Danail
Yanev, Pavel
author_sort Mollova-Sapundzhieva, Yordanka
collection PubMed
description β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and its C(5)-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively.
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spelling pubmed-106825422023-11-30 Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors Mollova-Sapundzhieva, Yordanka Angelov, Plamen Georgiev, Danail Yanev, Pavel Beilstein J Org Chem Full Research Paper β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and its C(5)-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively. Beilstein-Institut 2023-11-23 /pmc/articles/PMC10682542/ /pubmed/38033452 http://dx.doi.org/10.3762/bjoc.19.132 Text en Copyright © 2023, Mollova-Sapundzhieva et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Mollova-Sapundzhieva, Yordanka
Angelov, Plamen
Georgiev, Danail
Yanev, Pavel
Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title_full Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title_fullStr Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title_full_unstemmed Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title_short Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
title_sort synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10682542/
https://www.ncbi.nlm.nih.gov/pubmed/38033452
http://dx.doi.org/10.3762/bjoc.19.132
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