Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives

Objective: A series of novel fluorine containing (Z)-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2H)-one (IVa–IVe) and (E)-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives (Va–Ve) have been synthesized by using (E)-1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (IIIa–IIIe). Methods: The formation of the synthesized compounds was confirmed by IR, ¹H, ¹³C NMR, and mass spectral data. All synthesized compounds were screened for their antimicrobial activity. Results and Discussion: Most of the synthesized compounds have shown better antimicrobial activity as compared to standard drug. Molecular docking study against DNA gyrase could provide insights into binding modes and affinities. The binding affinity data was found to be in harmony with the experimental antimicrobial activities. Conclusions: Furthermore, analysis of the drug-like properties produced good results qualifying these leads as oral drug candidates.