| Title: |
Synthesis of novel bioactive lipophilic hydroxyalkyl esters and diesters based on hydroxyphenylacetic acids |
| Authors: |
Fochetti, Andrea; Villanova, Noemi; Lombardi, Andrea; Lelli, Veronica; Gazzilli, Yuri; Timperio, Anna Maria; Fabrizi, Giancarlo; Bernini, Roberta |
| Contributors: |
Fochetti, Andrea; Villanova, Noemi; Lombardi, Andrea; Lelli, Veronica; Gazzilli, Yuri; Timperio, Anna Maria; Fabrizi, Giancarlo; Bernini, Roberta |
| Publisher Information: |
Multidisciplinary Digital Publishing Institute (MDPI); MDPI AG, Grosspeteranlage 5, CH-4052 BASEL, SWITZERLAND |
| Publication Year: |
2025 |
| Collection: |
Sapienza Università di Roma: CINECA IRIS |
| Subject Terms: |
abts assay; dpph assay; antibacterial activity; antioxidant activity; butyl diarylacetate; hydroxyalkyl ester; hydroxyphenylacetic acid; lipophilicity |
| 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 Staphylococcus aureus and Escherichia coli, obtaining preliminary and promising results. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| Relation: |
info:eu-repo/semantics/altIdentifier/pmid/40807262; info:eu-repo/semantics/altIdentifier/wos/WOS:001549455500001; volume:30; issue:15; firstpage:1; lastpage:23; numberofpages:23; journal:MOLECULES; https://hdl.handle.net/11573/1747888 |
| DOI: |
10.3390/molecules30153087 |
| Availability: |
https://hdl.handle.net/11573/1747888; https://doi.org/10.3390/molecules30153087 |
| Rights: |
info:eu-repo/semantics/openAccess ; license:Creative commons ; license uri:http://creativecommons.org/licenses/by/4.0/ |
| Accession Number: |
edsbas.7FCF3E63 |
| Database: |
BASE |