Density Functional Theory and Molecular Docking Investigations of the Chemical and Antibacterial Activities for 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one

Abstract

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).

DFT, ADMET and Molecular Docking Investigations for the Antimicrobial Activity of 6,6′-Diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]

“…The molecular docking method is widely used to determine the proper orientation of drug molecules in the protein-active site as well as to measure their binding affinity. Previously, extensive molecular docking studies were conducted to explore the biological activity of many chemical materials [ 19 , 20 , 21 , 22 ]. Drug likeness criteria and an in silico ADMET profile are two other virtual screening tools for the adoption of compounds that may exhibit physiological activity and drug-like identity.…”

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

“…The global and local chemical reactivity parameters and the impact of pertinent substituted groups on the synthesized scaffold were also achieved by utilizing the DFT method. 21 …”

“…However, the density functional theory (DFT) method has also emerged as an influential technique for appraising the structural and spectral properties of organic compounds. The global and local chemical reactivity parameters and the impact of pertinent substituted groups on the synthesized scaffold were also achieved by utilizing the DFT method …”

“…The global and local chemical reactivity parameters and the impact of pertinent substituted groups on the synthesized scaffold were also achieved by utilizing the DFT method. 21 Hence, encouraged by these advances, we sought to explore the relevance of these reagents and methods in the synthesis of fused imidazo-pyridine scaffolds. In continuation of our research program focused on the development of synthetic methodologies 22−24 herein, we wish to disclose for the first time the ultrasonic-assisted synthesis of 2-phenylimidazo[1,2-a]pyridin-3-yl cyclohex-2-enones derivatives by employing iodine as a catalyst in aquatic conditions via one-pot MCR of 2-aminopyridine derivatives and pertinent aryl aldehydes along with dimedone embracing differently as one of the precursor substrates (Scheme 1).…”

Probing the Action of Screened Anticancer Triazole–Tetrazole Derivatives Against COVID-19 Using Molecular Docking and DFT Investigations

“…The success and popularity of the DFT method in the field of computational chemistry can be attributed to its high accuracy in describing small/large molecules over the course of many prior publications. 18,21 Molecular docking is a computational method for evaluating ligand-protein interactions with the help of virtual screening software. The applicability of the docking algorithm for virtual screening was proven by the accuracy of simulating the experimental binding pose.…”