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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6930484 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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