article · Molecules
Computational analysis of 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one reveals its chemical reactivity and potential antibacterial action against Staphylococcus aureus. Using density functional theory, the molecular structure was optimised, demonstrating high chemical reactivity driven by oxygen atoms and the pi-system, which serve as electron donor spots and electrophilic attack sites. Quantum chemical descriptors, including hardness, softness, electronegativity, and electrophilicity, were established to characterise molecular behaviour, with theoretical vibrational spectra matching experimental FT-IR and Raman measurements. Molecular docking simulations demonstrated strong binding affinity to penicillin-binding proteins of Staphylococcus aureus, yielding a binding energy of -7.40 kcal/mol. The compound formed six interactions with the bacterial protein, with the carbonyl group playing a central role through three hydrogen bonds and one van der Waals interaction.
Staphylococcus aureus poses persistent challenges in clinical medicine due to bacterial resistance. Identifying the electronic structure and binding mechanisms of candidate molecules helps explain how specific functional groups disrupt key bacterial targets. Computational assessments provide a foundational understanding of target engagement, enabling researchers to explore how particular chemical features might be exploited against bacterial proteins.
This work represents early-stage computational research relevant to antibacterial drug discovery targeting Staphylococcus aureus infections. Pharmaceutical researchers and medicinal chemists could use these structural and docking insights to guide the design of prospective antimicrobial agents. However, because the study is limited to theoretical modelling and spectroscopic verification, substantial in vitro testing and laboratory validation are required before any commercial application or clinical development can occur.
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The present investigation informs a descriptive study of 1-(4-Hydroxyphenyl) -3-phenylprop-2-en-1-one compound, by using density functional theory at B3LYP method with 6-311G** basis set. The oxygen atoms and π-system revealed a high chemical reactivity for the title compound as electron donor spots and active sites for an electrophilic attack. Quantum chemical parameters such as hardness (η), softness (S), electronegativity (χ), and electrophilicity (ω) were yielded as descriptors for the molecule's chemical behavior. The optimized molecular structure was obtained, and the experimental data were matched with geometrical analysis values describing the molecule's stable structure. The computed FT-IR and Raman vibrational frequencies were in good agreement with those observed experimentally. In a molecular docking study, the inhibitory potential of the studied molecule was evaluated against the penicillin-binding proteins of Staphylococcus aureus bacteria. The carbonyl group in the molecule was shown to play a significant role in antibacterial activity, four bonds were formed by the carbonyl group with the key protein of the bacteria (three favorable hydrogen bonds plus one van der Waals bond) out of six interactions. The strong antibacterial activity was also indicated by the calculated high binding energy (-7.40 kcal/mol).
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DOI: 10.3390/molecules26123631
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