Synthesis, Characterization, and Biological Evaluation of Hydroxybenzaldehyde Derivatives of Fluorinated Chalcones with Enhanced Antimicrobial Activity

A series of novel fluorinated chalcone derivatives bearing a hydroxybenzaldehyde moiety was synthesized and comprehensively characterized. The synthetic protocol involved the condensation of various hydroxy-substituted benzaldehydes with fluorinated acetophenones under basic conditions. The structures of the target compounds were elucidated using 1H-NMR, 13C-NMR, IR, and mass spectrometry techniques. The synthesized compounds were evaluated for their antimicrobial activity against a panel of clinically relevant bacterial and fungal strains, including Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans. Several derivatives demonstrated potent antimicrobial properties, with minimum inhibitory concentration (MIC) values ranging from 5 to 25 μg/mL. Structure-activity relationship (SAR) studies revealed that the position and number of hydroxyl groups, as well as the nature of the fluorine substituents, played a crucial role in modulating the antimicrobial efficacy of the chalcone analogues. This study highlights the potential of fluorinated hydroxychalcone derivatives as promising antimicrobial agents and provides a framework for the rational design of future therapeutic candidates