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Article

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

CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal
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Authors to whom correspondence should be addressed.
Present address: Department of Biology and Biotechnology, University of Pavia, Via Ferrata 1, 27100 Pavia, Italy.
Academic Editors: Ionel Mangalagiu and John Spencer
Molecules 2019, 24(23), 4214; https://doi.org/10.3390/molecules24234214
Received: 13 September 2019 / Revised: 26 October 2019 / Accepted: 19 November 2019 / Published: 20 November 2019
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 4B10B) 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. View Full-Text
Keywords: chromone-2-carboxylic acids; microwave-assisted reaction; multitarget ligands chromone-2-carboxylic acids; microwave-assisted reaction; multitarget ligands
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MDPI and ACS Style

Cagide, F.; Oliveira, C.; Reis, J.; Borges, F. Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands. Molecules 2019, 24, 4214. https://doi.org/10.3390/molecules24234214

AMA Style

Cagide F, Oliveira C, Reis J, Borges F. Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands. Molecules. 2019; 24(23):4214. https://doi.org/10.3390/molecules24234214

Chicago/Turabian Style

Cagide, Fernando, Catarina Oliveira, Joana Reis, and Fernanda Borges. 2019. "Optimizing the Synthetic Route of Chromone-2-carboxylic Acids: A Step forward to Speed-up the Discovery of Chromone-based Multitarget-directed Ligands" Molecules 24, no. 23: 4214. https://doi.org/10.3390/molecules24234214

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