Synthesis of Novel Bioactive Lipophilic Hydroxyalkyl Esters and Diesters Based on Hydroxyphenylacetic Acids
Author(s)
Date Issued
2025
Type
article
Volume
30
Issue
15
Journal
Abstract
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.
File(s)![Thumbnail Image]()
Name
molecules-30-03087.pdf
Size
1.08 MB
Format
Adobe PDF
Checksum (MD5)
22736cc05d315dfb50357b24cc79729e