{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T02:14:58Z","timestamp":1788833698633,"version":"build-2803163510"},"reference-count":50,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2021,6,14]],"date-time":"2021-06-14T00:00:00Z","timestamp":1623628800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 \u03c0-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 (\u03b7), softness (S), electronegativity (\u03c7), and electrophilicity (\u03c9) were yielded as descriptors for the molecule\u2019s chemical behavior. The optimized molecular structure was obtained, and the experimental data were matched with geometrical analysis values describing the molecule\u2019s 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 (\u22127.40 kcal\/mol).<\/jats:p>","DOI":"10.3390\/molecules26123631","type":"journal-article","created":{"date-parts":[[2021,6,14]],"date-time":"2021-06-14T22:25:46Z","timestamp":1623709546000},"page":"3631","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":56,"title":["Density Functional Theory and Molecular Docking Investigations of the Chemical and Antibacterial Activities for 1-(4-Hydroxyphenyl)-3-phenylprop-2-en-1-one"],"prefix":"10.3390","volume":"26","author":[{"given":"Ahmed M.","family":"Deghady","sequence":"first","affiliation":[{"name":"Basic Science Department, Higher Technological Institute, 10th of Ramadan City 44629, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rageh K.","family":"Hussein","sequence":"additional","affiliation":[{"name":"Physics Department, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5116-3622","authenticated-orcid":false,"given":"Abdulrahman G.","family":"Alhamzani","sequence":"additional","affiliation":[{"name":"Chemistry Department, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abeer","family":"Mera","sequence":"additional","affiliation":[{"name":"Physics Department, College of Arts and Science, Prince Sattam Bin Abdulaziz University, Wadi Addawasir 11991, Saudi Arabia"},{"name":"Physics Department, Faculty of Science, Kafrelsheikh University, Kafrelsheikh 33516, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,6,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1007\/s10311-019-00959-w","article-title":"Chalcone Synthesis, Properties and Medicinal Applications: A Review","volume":"18","author":"Rammohan","year":"2020","journal-title":"Environ. Chem. Lett."},{"key":"ref_2","first-page":"13672","article-title":"Chalcones as Sythons for Heterocyclic Compounds- A Review","volume":"12","author":"Owaba","year":"2020","journal-title":"Int. J. Curr. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"239","DOI":"10.13181\/mji.v23i4.1015","article-title":"Antioxidant Properties of Flavonoids","volume":"23","author":"Banjarnahor","year":"2015","journal-title":"Med. J. Indones."},{"key":"ref_4","first-page":"388","article-title":"Diverse Molecular Targets for Chalcones with Varied Bioactivities","volume":"5","author":"Zhou","year":"2015","journal-title":"Med. Chem."},{"key":"ref_5","first-page":"286","article-title":"Antimicrobial, Anti-Inflammatory and Antioxidant Activities of Polyoxygenated Chalcones","volume":"30","author":"Osorio","year":"2019","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_6","first-page":"20","article-title":"Chemical and Biological Potentials of Chalcones: A Review","volume":"1","author":"Yazdan","year":"2015","journal-title":"Org. Med. Chem. Int. J."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"129743","DOI":"10.1016\/j.molstruc.2020.129743","article-title":"Comparative Conformational Study of a New Terpenoid-like Chalcone","volume":"1228","author":"Silva","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"110675","DOI":"10.1016\/j.molliq.2019.03.134","article-title":"Experimental and Theoretical Study of the Structure, Frontier Molecular Orbital, Tautomerism and Spectral Analysis of 3-(p-Substituted Phenyl)-5-Phenyl-1H-Pyrazole","volume":"287","author":"Ibnaouf","year":"2019","journal-title":"J. Mol. Liq."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Bonvicini, F., Gentilomi, G., Bressan, F., Gobbi, S., Rampa, A., Bisi, A., and Belluti, F. (2019). Functionalization of the Chalcone Scaffold for the Discovery of Novel Lead Compounds Targeting Fungal Infections. Molecules, 24.","DOI":"10.3390\/molecules24020372"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Al-Anazi, M., Al-Najjar, B., and Khairuddean, M. (2018). Structure-Based Drug Design Studies Toward the Discovery of Novel Chalcone Derivatives as Potential Epidermal Growth Factor Receptor (EGFR) Inhibitors. Molecules, 23.","DOI":"10.3390\/molecules23123203"},{"key":"ref_11","first-page":"479","article-title":"Catalytic Synthesis of 1,3-Diaryl-2-Propene-1-Ones by Using Heteropolyacids as heterogeneous recyclable green catalysts","volume":"46","author":"Gharib","year":"2014","journal-title":"Bulg. Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.4314\/tjpr.v13i12.3","article-title":"Inclusion Mechanism and Heat Stability of the Complex of 4\u2032-Hydroxychalcone and Hydroxypropyl-\u03b2-Cyclodextrin","volume":"13","author":"Guo","year":"2015","journal-title":"Trop. J. Pharm. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1273","DOI":"10.1016\/j.bmc.2009.12.029","article-title":"A New Series of Flavones, Thioflavones, and Flavanones as Selective Monoamine Oxidase-B Inhibitors","volume":"18","author":"Chimenti","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_14","first-page":"103","article-title":"Synthesis of Some Heterocyclic Compounds Derived From Chalcones","volume":"2","author":"Elarfi","year":"2012","journal-title":"IIb"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.molstruc.2017.08.072","article-title":"Molecular Structure, Nonlinear Optical Studies and Spectroscopic Analysis of Chalcone Derivative (2E)-3-[4-(Methylsulfanyl) Phenyl]-1-(3-Bromophenyl) Prop-2-En-1-One by DFT Calculations","volume":"1150","author":"Kumar","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1016\/j.molstruc.2014.07.074","article-title":"Synthesis, Characterization and Computational Study on Ethyl 4-(3-Furan-2yl-Acryloyl)-3,5-Dimethyl-1H-Pyrrole-2-Carboxylate","volume":"1076","author":"Singh","year":"2014","journal-title":"J. Mol. Struct."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/j.molstruc.2018.10.035","article-title":"Molecular Structure, Frontier Molecular Orbital and Spectral Analysis of Dimethylamino Chalcones Efficient Lasing Dyes","volume":"1178","author":"Elzupir","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"12046","DOI":"10.1088\/1742-6596\/1083\/1\/012046","article-title":"Molecular Structure Investigation On Organic Chalcone Derivative of (E)-3-(4-Bromothiophen-2-1-(3-Nitrophenyl)Prop-2-En-1-One: A Combined Experimental and Theoretical Study","volume":"1083","author":"Arshad","year":"2018","journal-title":"J. Phys. Conf. Ser."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4274","DOI":"10.20964\/2020.05.11","article-title":"Density Functional Theory Investigation of Some Pyridine Dicarboxylic Acids Derivatives as Corrosion Inhibitors","volume":"15","author":"Hassan","year":"2020","journal-title":"Int. J. Electrochem. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"606","DOI":"10.1016\/j.molstruc.2019.05.122","article-title":"New Halogenated Chalcones: Synthesis, Crystal Structure, Spectroscopic and Theoretical Analyses for Third-Order Nonlinear Optical Properties","volume":"1195","author":"Zaini","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.molstruc.2014.12.052","article-title":"Synthesis, Molecular Structure, Spectroscopic Characterization and Quantum Chemical Calculation Studies of (2E)-1-(5-Chlorothiophen-2-Yl)-3-(2,3,4-Trimethoxyphenyl)Prop-2-En-1-One","volume":"1085","author":"Govindarasu","year":"2015","journal-title":"J. Mol. Struct."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1186\/1752-153X-7-17","article-title":"Experimental and Quantum Chemical Studies of a Novel Synthetic Prenylated Chalcone","volume":"7","year":"2013","journal-title":"Chem. Cent. J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.molstruc.2018.02.087","article-title":"Molecular Docking Studies on Fluoro-Substituted Chalcones as Potential DprE1 Enzyme Inhibitors","volume":"1164","author":"Yalcin","year":"2018","journal-title":"J. Mol. Struct."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"129979","DOI":"10.1016\/j.molstruc.2021.129979","article-title":"Molecular Docking Identification for the Efficacy of Some Zinc Complexes with Chloroquine and Hydroxychloroquine against Main Protease of COVID-19","volume":"1231","author":"Hussein","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4191","DOI":"10.1007\/s00044-015-1467-9","article-title":"Synthesis, Molecular Docking and Biological Evaluation of Novel Bis-Pyrazole Derivatives for Analgesic, Anti-Inflammatory and Antimicrobial Activities","volume":"24","author":"Nayak","year":"2015","journal-title":"Med. Chem. Res."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/S0009-2614(01)00771-0","article-title":"OH Stretching Vibrations of the Phenol (H2O)1+ Cation","volume":"344","author":"Gerhards","year":"2001","journal-title":"Chem. Phys. Lett."},{"key":"ref_27","unstructured":"Meyers, R.A. (2006). Interpretation of Infrared Spectra, A Practical Approach. Encyclopedia of Analytical Chemistry, John Wiley & Sons, Ltd."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/0009-2614(70)85042-4","article-title":"The Stretching Vibration of Carbonyl Groups in Cyclic Ketones","volume":"5","author":"Galabov","year":"1970","journal-title":"Chem. Phys. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Balan, V., Mihai, C.-T., Cojocaru, F.-D., Uritu, C.-M., Dodi, G., Botezat, D., and Gardikiotis, I. (2019). Vibrational Spectroscopy Fingerprinting in Medicine: From Molecular to Clinical Practice. Materials, 12.","DOI":"10.3390\/ma12182884"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2015\/489162","article-title":"Infrared Spectroscopic Characterization of Photoluminescent Polymer Nanocomposites","volume":"2015","author":"Gipson","year":"2015","journal-title":"J. Spectrosc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"o86","DOI":"10.1107\/S1600536801021328","article-title":"1-(4-Hydroxyphenyl)-3-Phenylprop-2-En-1-One","volume":"58","author":"Parthasarathi","year":"2002","journal-title":"Acta Crystallogr. Sect. E Struct. Rep. Online"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Domingo, L., R\u00edos-Guti\u00e9rrez, M., and P\u00e9rez, P. (2016). Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity. Molecules, 21.","DOI":"10.3390\/molecules21060748"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"174101","DOI":"10.1063\/1.3491272","article-title":"On Koopmans\u2019 Theorem in Density Functional Theory","volume":"133","author":"Tsuneda","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4615","DOI":"10.1021\/jo800572a","article-title":"Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study","volume":"73","author":"Domingo","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"928","DOI":"10.2478\/s11532-010-0058-3","article-title":"An Ab Initio Simulation of the UV\/Visible Spectra of Substituted Chalcones","volume":"8","author":"Xue","year":"2010","journal-title":"Open Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"7168","DOI":"10.1039\/c1ob05856h","article-title":"The Nucleophilicity N Index in Organic Chemistry","volume":"9","author":"Domingo","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1118","DOI":"10.1515\/chempap-2015-0113","article-title":"Synthesis, Biological Evaluation, Quantitative-SAR and Docking Studies of Novel Chalcone Derivatives as Antibacterial and Antioxidant Agents","volume":"69","author":"Alam","year":"2015","journal-title":"Chem. Pap."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"e1501240","DOI":"10.1126\/sciadv.1501240","article-title":"Regulation of Protein-Ligand Binding Affinity by Hydrogen Bond Pairing","volume":"2","author":"Chen","year":"2016","journal-title":"Sci. Adv."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2267","DOI":"10.1021\/acsomega.9b03479","article-title":"Privileged Scaffold Chalcone: Synthesis, Characterization and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic and Chemoinformatics Approaches","volume":"5","author":"Singh","year":"2020","journal-title":"ACS Omega"},{"key":"ref_40","unstructured":"John Wiley & Sons, Inc (2021, May 20). SpectraBase; SpectraBase Compound ID=15yGNIg0GtJ SpectraBase Spectrum ID=BpE7xdvOvip. Available online: https:\/\/spectrabase.com\/spectrum\/BpE7xdvOvip."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1016\/S0009-2614(97)00207-8","article-title":"On the Parameterization of the Local Correlation Functional. What Is Becke-3-LYP?","volume":"268","author":"Hertwig","year":"1997","journal-title":"Chem. Phys. Lett."},{"key":"ref_42","first-page":"361","article-title":"Perspective on \u201cDensity Functional Thermochemistry. III. The Role of Exact Exchange\u201d","volume":"103","author":"Raghavachari","year":"2000","journal-title":"Theor. Chem. Acc. Theory Comput. Model. Theor. Chim. Acta"},{"key":"ref_43","unstructured":"Frisch, M.J., Trucks, G.W., and Schlegel, H.B. (2009). Gaussian 09, Gaussian Inc."},{"key":"ref_44","unstructured":"Dennington, R., Keith, T., and Millam, J. (2009). Gauss View, Semichem Inc."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Reed, P., Atilano, M.L., Alves, R., Hoiczyk, E., Sher, X., Reichmann, N.T., Pereira, P.M., Roemer, T., Filipe, S.R., and Pereira-Leal, J.B. (2015). Staphylococcus Aureus Survives with a Minimal Peptidoglycan Synthesis Machine but Sacrifices Virulence and Antibiotic Resistance. PLoS Pathog., 11.","DOI":"10.1371\/journal.ppat.1004891"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"656","DOI":"10.1515\/znc-1988-9-1006","article-title":"On the Relationships between Molecular Conformation, Affinity towards Penicillin-Binding Proteins, and Biological Activity of Penicillin G-Sulfoxide","volume":"43","author":"Beise","year":"1988","journal-title":"Z. Naturforschung C"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1128\/JB.00822-09","article-title":"Molecular Basis for the Role of Staphylococcus Aureus Penicillin Binding Protein 4 in Antimicrobial Resistance","volume":"192","author":"Navratna","year":"2010","journal-title":"J. Bacteriol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"11","DOI":"10.3390\/antibiotics2010011","article-title":"The Staphylococcus Aureus Membrane Protein SA2056 Interacts with Peptidoglycan Synthesis Enzymes","volume":"2","author":"Quiblier","year":"2013","journal-title":"Antibiotics"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"128049","DOI":"10.1016\/j.molstruc.2020.128049","article-title":"Ferrocenyl Chalcone Derivative (E)-3-(2-Methylpyrimidin-5-Yl)-1-Ferroceynlprop-2-En-1-One: Synthesis, Structural Analysis, Docking Study and Their Antibacterial Evaluation","volume":"1210","author":"Twinkle","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_50","unstructured":"Dassault Syst\u00e8mes BIOVIA (2016). Discovery Studio Modelling Environment, Release 2017, Dassault Syst\u00e8mes."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3631\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:14:06Z","timestamp":1760163246000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/12\/3631"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,6,14]]},"references-count":50,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2021,6]]}},"alternative-id":["molecules26123631"],"URL":"https:\/\/doi.org\/10.3390\/molecules26123631","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,6,14]]}}}