Synthesis, structural elucidation, and antimicrobial evaluation of (2E)-3-(4-fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one: insights from experimental and computational studies

The compound (2E)-3-(4-Fluorophenyl)-1-(4-isopropylphenyl)prop-2-en-1-one (FIPP) was synthesized via Claisen-Schmidt condensation and fully characterized using FT-IR, 1H and 13C NMR, HRMS, and single-crystal X-ray diffraction. HRMS analysis validated the molecular composition and purity, while single-crystal X-ray diffraction revealed that FIPP crystallizes in the orthorhombic system [space group P2(1)2(1)2(1)] with unit cell parameters a = 6.4704 (4) Å, b = 12.9304 (8) Å, c = 16.7181 (11) Å, α = β = γ = 90°, and Z = 4. DFT/B3LYP calculations with a 6–311++G(d,p) basis set showed strong agreement with experimental data, confirming the reliability of the computational approach. Antimicrobial studies demonstrated moderate antibacterial activity against gram-negative (Escherichia coli, Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus, Streptococcus pyogenes) bacteria, as well as moderate antifungal activity against Candida albicans, Aspergillus niger, and Aspergillus clavatus. Docking studies against 4URO (antibacterial target) and 5V5Z (antifungal target) gave docking scores of − 8.1 kcal/mol and − 9.1 kcal/mol, respectively, indicating strong binding interactions through hydrogen bonding, electrostatic, and hydrophobic forces. ADME profiling revealed high gastrointestinal absorption, blood–brain barrier permeability, selective P450 inhibition, and moderate bioavailability, highlighting ’s pharmacokinetic potential.