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Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands

6-Bromochromone-2-carboxylic acid (3) was synthesized by a microwave-assisted process. The optimization of the reaction was performed varying parameters, such as type of base/number of reagent equivalents, solvent, temperature and reaction time. The yield of the reaction was improved to 87%. The new...

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Autores principales: Cagide, Fernando, Oliveira, Catarina, Reis, Joana, Borges, Fernanda
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930484/
https://www.ncbi.nlm.nih.gov/pubmed/31757041
http://dx.doi.org/10.3390/molecules24234214
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author Cagide, Fernando
Oliveira, Catarina
Reis, Joana
Borges, Fernanda
author_facet Cagide, Fernando
Oliveira, Catarina
Reis, Joana
Borges, Fernanda
author_sort Cagide, Fernando
collection PubMed
description 6-Bromochromone-2-carboxylic acid (3) was synthesized by a microwave-assisted process. The optimization of the reaction was performed varying parameters, such as type of base/number of reagent equivalents, solvent, temperature and reaction time. The yield of the reaction was improved to 87%. The new synthetic route is versatile as several chromone-2-carboxylic acids (compounds 4B–10B) were obtained with good yields (54–93%). Only in the case of the nitro substituent (compound 11B), an ester was obtained instead of the desired carboxylic acid. Following this synthetic route chromone carboxylic acids can be attained with a high degree of purity, without the need of the tedious and expensive purification processes through column chromatography. The reaction is safe, cost-effective, fast and robust, and can be used in the development of concise and diversity-oriented libraries based on chromone scaffold. The overall study can be looked as a step forward to speed-up the discovery of chromone-based multitarget-directed ligands.
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spelling pubmed-69304842019-12-26 Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands Cagide, Fernando Oliveira, Catarina Reis, Joana Borges, Fernanda Molecules Article 6-Bromochromone-2-carboxylic acid (3) was synthesized by a microwave-assisted process. The optimization of the reaction was performed varying parameters, such as type of base/number of reagent equivalents, solvent, temperature and reaction time. The yield of the reaction was improved to 87%. The new synthetic route is versatile as several chromone-2-carboxylic acids (compounds 4B–10B) were obtained with good yields (54–93%). Only in the case of the nitro substituent (compound 11B), an ester was obtained instead of the desired carboxylic acid. Following this synthetic route chromone carboxylic acids can be attained with a high degree of purity, without the need of the tedious and expensive purification processes through column chromatography. The reaction is safe, cost-effective, fast and robust, and can be used in the development of concise and diversity-oriented libraries based on chromone scaffold. The overall study can be looked as a step forward to speed-up the discovery of chromone-based multitarget-directed ligands. MDPI 2019-11-20 /pmc/articles/PMC6930484/ /pubmed/31757041 http://dx.doi.org/10.3390/molecules24234214 Text en © 2019 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Cagide, Fernando
Oliveira, Catarina
Reis, Joana
Borges, Fernanda
Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title_full Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title_fullStr Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title_full_unstemmed Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title_short Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands
title_sort optimizing the synthetic route of chromone-2-carboxylic acids: a step forward to speed-up the discovery of chromone-based multitarget-directed ligands
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930484/
https://www.ncbi.nlm.nih.gov/pubmed/31757041
http://dx.doi.org/10.3390/molecules24234214
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