Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids
Novel lipophilic hydroxyalkyl esters were synthetized by Fischer esterification in good to excellent yields (60–96%) from a panel of hydroxyphenylacetic acids and increasing chain length (2 to 8 carbon atoms) α,ω-diols. The in vitro antioxidant activity of these compounds was evaluated by DPPH and A...
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| Language: | English |
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MDPI AG
2025-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/15/3087 |
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| author | Andrea Fochetti Noemi Villanova Andrea Lombardi Veronica Lelli Yuri Gazzilli Anna Maria Timperio Giancarlo Fabrizi Roberta Bernini |
| author_facet | Andrea Fochetti Noemi Villanova Andrea Lombardi Veronica Lelli Yuri Gazzilli Anna Maria Timperio Giancarlo Fabrizi Roberta Bernini |
| author_sort | Andrea Fochetti |
| collection | DOAJ |
| description | Novel lipophilic hydroxyalkyl esters were synthetized by Fischer esterification in good to excellent yields (60–96%) from a panel of hydroxyphenylacetic acids and increasing chain length (2 to 8 carbon atoms) α,ω-diols. The in vitro antioxidant activity of these compounds was evaluated by DPPH and ABTS assays. Hydroxybutyl esters and hydroxyphenylacetic acids were used as starting materials for the synthesis of novel lipophilic diesters (butyl diarylacetates) using Mitsunobu reaction. The final products were isolated in moderate to good yields (40–78%), and their structure–antioxidant activity relationships are discussed. Compounds bearing the catechol moiety on one of the two aromatic rings and high lipophilicity proved to be the strongest antioxidants and were selected for testing as antibacterials against <i>Staphylococcus aureus</i> and <i>Escherichia coli</i>, obtaining preliminary and promising results. |
| format | Article |
| id | doaj-art-e282d3eff54d4b0b850a59de3e876cc4 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-e282d3eff54d4b0b850a59de3e876cc42025-08-20T03:36:27ZengMDPI AGMolecules1420-30492025-07-013015308710.3390/molecules30153087Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic AcidsAndrea Fochetti0Noemi Villanova1Andrea Lombardi2Veronica Lelli3Yuri Gazzilli4Anna Maria Timperio5Giancarlo Fabrizi6Roberta Bernini7Department of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via San Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via San Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via San Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Ecological and Biological Sciences (DEB), University of Tuscia, 01100 Viterbo, ItalyDepartment of Chemistry and Technology of Drugs, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, ItalyDepartment of Ecological and Biological Sciences (DEB), University of Tuscia, 01100 Viterbo, ItalyDepartment of Chemistry and Technology of Drugs, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via San Camillo de Lellis, 01100 Viterbo, ItalyNovel lipophilic hydroxyalkyl esters were synthetized by Fischer esterification in good to excellent yields (60–96%) from a panel of hydroxyphenylacetic acids and increasing chain length (2 to 8 carbon atoms) α,ω-diols. The in vitro antioxidant activity of these compounds was evaluated by DPPH and ABTS assays. Hydroxybutyl esters and hydroxyphenylacetic acids were used as starting materials for the synthesis of novel lipophilic diesters (butyl diarylacetates) using Mitsunobu reaction. The final products were isolated in moderate to good yields (40–78%), and their structure–antioxidant activity relationships are discussed. Compounds bearing the catechol moiety on one of the two aromatic rings and high lipophilicity proved to be the strongest antioxidants and were selected for testing as antibacterials against <i>Staphylococcus aureus</i> and <i>Escherichia coli</i>, obtaining preliminary and promising results.https://www.mdpi.com/1420-3049/30/15/3087hydroxyphenylacetic acidshydroxyalkyl estersbutyl diarylacetateslipophilicityantioxidant activityDPPH assay |
| spellingShingle | Andrea Fochetti Noemi Villanova Andrea Lombardi Veronica Lelli Yuri Gazzilli Anna Maria Timperio Giancarlo Fabrizi Roberta Bernini Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids Molecules hydroxyphenylacetic acids hydroxyalkyl esters butyl diarylacetates lipophilicity antioxidant activity DPPH assay |
| title | Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids |
| title_full | Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids |
| title_fullStr | Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids |
| title_full_unstemmed | Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids |
| title_short | Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids |
| title_sort | synthesis of novel bioactive lipophilic hydroxyalkyl esters and diesters based on hydroxyphenylacetic acids |
| topic | hydroxyphenylacetic acids hydroxyalkyl esters butyl diarylacetates lipophilicity antioxidant activity DPPH assay |
| url | https://www.mdpi.com/1420-3049/30/15/3087 |
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