{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,4]],"date-time":"2026-11-04T14:57:23Z","timestamp":1793804243491,"version":"4.6.1"},"reference-count":86,"publisher":"American Chemical Society (ACS)","issue":"25","license":[{"start":{"date-parts":[[2025,6,13]],"date-time":"2025-06-13T00:00:00Z","timestamp":1749772800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004477","name":"Universiteit Stellenbosch","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004477","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001321","name":"National Research Foundation","doi-asserted-by":"publisher","award":["CPRR23041794158"],"award-info":[{"award-number":["CPRR23041794158"]}],"id":[{"id":"10.13039\/501100001321","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,7,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Two halogenated quinoline derivatives, namely, N-(4-fluorophenyl)-1-(quinoline-2-yl)\u00admethanimine (Q4F) and N-(3-chloro-4-fluorophenyl)-1-(quinoline-2-yl)\u00admethanimine (Q3Cl4F) were synthesized and elucidated by spectroscopic techniques. The molecular structures of Q4F and Q3Cl4F revealed that the azomethine functional group in both compounds is coplanar to the quinoline ring as well as the phenyl ring, as is evident by N2\u2013C8\u2013C7\u2013N1 and C7\u2013N1\u2013C4\u2013C3 torsion angles. In the crystal packing of both compounds, there exists intermolecular C\ue5f8H\u00b7\u00b7\u00b7N hydrogen bonding. In silico approaches were explored to probe the inhibitory potential of the two compounds against MAO-A and MAO-B, proteins that have been implicated in Parkinson\u2019s and neurodegenerative diseases. Docking studies revealed that Q3Cl4F and Q4F exhibit superior binding affinities compared to reference drugs, with Q3Cl4F demonstrating a binding score of \u22127.24 kcal\/mol for MAO-A and \u22128.37 kcal\/mol for MAO-B, outperforming harmine (\u22126.57 kcal\/mol) and rasagiline (\u22126.47 kcal\/mol). Thermodynamic analysis further confirmed the stability of Q3Cl4F and Q4F interactions, with \u0394Gbind values of \u221238.24 and \u221235.80 kcal\/mol for MAO-A, respectively, surpassing that of harmine (\u221227.82 kcal\/mol). Similarly, for MAO-B, Q3Cl4F and Q4F achieved \u0394G bind values of \u221235.02 and \u221233.49 kcal\/mol, respectively, exceeding rasagiline (\u221232.95 kcal\/mol). Post-MD simulations analysis revealed that the complexes of Q4F\/Q3Cl4F with MAO-A and MAO-B displayed stronger structural stability than reference drugs, as depicted by their lower RMSF, RMSD, and RoG values. For MAO-A, harmine (reference drug) had an RMSD of 3.508 \u00b1 1.328 \u00c5, RoG of 24.916 \u00b1 0.364 \u00c5, and RMSF of 5.990 \u00b1 2.984 \u00c5, whereas Q3Cl4F, which outshined both reference drug and Q4F, had an RMSD of 2.683 \u00b1 0.625 \u00c5, RoG of 24.890 \u00b1 0.198 \u00c5, and RMSF of 6.307 \u00b1 2.580 \u00c5. Quantum chemical calculations and charge distribution parameters were done in gaseous and aqueous phases using different basis sets. Compound Q4F was observed to be more chemically reactive and less stable due to its lower energy band gap (\u0394E) relative to that of Q3Cl4F. The influence of solvation was quantified, showing that aqueous environment enhances molecular stability and reduces reactivity.<\/jats:p>","DOI":"10.1021\/acsomega.4c11530","type":"journal-article","created":{"date-parts":[[2025,6,13]],"date-time":"2025-06-13T19:36:49Z","timestamp":1749843409000},"page":"26500-26519","source":"Crossref","is-referenced-by-count":11,"title":["Investigating the Inhibitory Potential of Halogenated\nQuinoline Derivatives against MAO\u2011A and MAO-B: Synthesis, Crystal\nStructure, Density Functional Theory, and Molecular Dynamics Simulations"],"prefix":"10.1021","volume":"10","author":[{"given":"Segun D.","family":"Oladipo","sequence":"first","affiliation":[{"name":"Stellenbosch University , , Private Bag X1 , ,","place":["Matieland, South Africa, 7602"]},{"name":"Olabisi Onabanjo University , , P.M.B , ,","place":["Ago-Iwoye, Nigeria, 2002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5371-358X","authenticated-orcid":true,"given":"Robert C.","family":"Luckay","sequence":"additional","affiliation":[{"name":"Stellenbosch University , , Private Bag X1 , ,","place":["Matieland, South Africa, 7602"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samuel O.","family":"Olalekan","sequence":"additional","affiliation":[{"name":"Olabisi Onabanjo University , , Sagamu Campus, Sagamu, Ogun State , ,","place":["Ago-Iwoye, Nigeria, 2002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abosede A.","family":"Badeji","sequence":"additional","affiliation":[{"name":"Tai Solarin University of Education , , Ijagun, Ogun State , ,","place":["Ago-Iwoye, Nigeria, 120103"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nonkosi","family":"Matinise","sequence":"additional","affiliation":[{"name":"Stellenbosch University , , Private Bag X1 , ,","place":["Matieland, South Africa, 7602"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fulufhelo","family":"Tshikhudo","sequence":"additional","affiliation":[{"name":"University of Venda , , Private Bag X5050 , ,","place":["Thohoyandou, South Africa, 0950"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,6,13]]},"reference":[{"key":"2026081811260139600_cit1","doi-asserted-by":"publisher","first-page":"105798","DOI":"10.1016\/j.neuint.2024.105798","article-title":"Combating Parkinson\u2019s disease with plant-derived\npolyphenols: Targeting oxidative stress and neuroinflammation","volume":"178","author":"Gahtani","year":"2024","journal-title":"Neurochem. Int."},{"key":"2026081811260139600_cit2","doi-asserted-by":"publisher","first-page":"1015","DOI":"10.1002\/mds.23669","article-title":"Milestones\nin Parkinson\u2019s\ndisease\ue5f8clinical and pathologic features","volume":"26","author":"Halliday","year":"2011","journal-title":"Mov. Disord."},{"key":"2026081811260139600_cit3","doi-asserted-by":"publisher","first-page":"4271","DOI":"10.1016\/j.csbj.2022.08.017","article-title":"Network metrics, structural dynamics\nand density functional theory calculations identified a novel Ursodeoxycholic\nAcid derivative against therapeutic target Parkin for Parkinson\u2019s\ndisease","volume":"20","author":"Naha","year":"2022","journal-title":"Comput. Struct. Biotechnol. J."},{"key":"2026081811260139600_cit4","doi-asserted-by":"publisher","first-page":"104749","DOI":"10.1016\/j.neubiorev.2022.104749","article-title":"Prevalence and clinical\naspects of depression in Parkinson\u2019s\ndisease: a systematic review and meta-analysis of 129 studies","volume":"141","author":"Cong","year":"2022","journal-title":"Neurosci. Biobehav. Rev."},{"key":"2026081811260139600_cit5","doi-asserted-by":"publisher","first-page":"231","DOI":"10.1002\/mdc3.13122","article-title":"Prevalence\nof non-motor symptoms\nand non-motor fluctuations in Parkinson\u2019s disease using the\nMDS-NMS","volume":"8","author":"Rodriguez-Blazquez","year":"2021","journal-title":"Mov. Disord. Clin. Pract."},{"key":"2026081811260139600_cit6","doi-asserted-by":"publisher","first-page":"650","DOI":"10.1172\/JCI37617","article-title":"Parkin, PINK1, and DJ-1 form a ubiquitin\nE3 ligase complex promoting unfolded protein degradation","volume":"119","author":"Xiong","year":"2009","journal-title":"J. Clinical invest."},{"key":"2026081811260139600_cit7","doi-asserted-by":"publisher","first-page":"118","DOI":"10.1016\/j.cbi.2011.01.006","article-title":"Dopamine-derived\nbiological reactive intermediates and protein modifications: Implications\nfor Parkinson\u2019s disease","volume":"192","author":"Jinsmaa","year":"2011","journal-title":"Chem.-Biological\nInteract."},{"key":"2026081811260139600_cit8","doi-asserted-by":"publisher","first-page":"36","DOI":"10.1016\/j.parkreldis.2018.12.004","article-title":"Parkinson\u2019s disease in Nigeria:\na review of published studies and recommendations for future research","volume":"62","author":"Oluwole","year":"2019","journal-title":"Parkinsonism Relat. Disord."},{"key":"2026081811260139600_cit9","doi-asserted-by":"crossref","first-page":"521","DOI":"10.3233\/JPD-230291","article-title":"The Prevalence\nof Parkinson\u2019s Disease in Poland:\nRegional and Sex-Related Differences","volume":"14","author":"S\u0301mi\u0142owska","year":"2024","journal-title":"J. Parkinson\u2019s\nDis."},{"key":"2026081811260139600_cit10","doi-asserted-by":"publisher","first-page":"776847","DOI":"10.3389\/fpubh.2021.776847","article-title":"Global trends\nin the incidence, prevalence, and years lived with\ndisability of Parkinson\u2019s disease in 204 countries\/territories\nfrom 1990 to 2019","volume":"9","author":"Ou","year":"2021","journal-title":"Front. Public Health"},{"key":"2026081811260139600_cit11","doi-asserted-by":"publisher","first-page":"572","DOI":"10.2174\/1871527319666200722153156","article-title":"Levodopa therapy for\nParkinson\u2019s disease: history, current status and perspectives","volume":"19","author":"Bogetofte","year":"2020","journal-title":"CNS Neurol. Disord. Drug Targets"},{"key":"2026081811260139600_cit12","doi-asserted-by":"publisher","first-page":"45","DOI":"10.4103\/aomd.aomd_37_22","article-title":"Adverse effects\nof medications used\nto treat motor symptoms of Parkinson\u2019s disease: A narrative\nreview","volume":"6","author":"Mishal","year":"2023","journal-title":"Ann. Mov. Disord."},{"key":"2026081811260139600_cit13","doi-asserted-by":"publisher","first-page":"319","DOI":"10.17344\/acsi.2023.8484","article-title":"Synthesis, Characterization and Biological Activity\nEvaluation of Novel Quinoline Derivatives as Antibacterial Drug","volume":"71","author":"Kassar","year":"2024","journal-title":"Acta Chim. Slov."},{"key":"2026081811260139600_cit14","doi-asserted-by":"publisher","first-page":"909","DOI":"10.3390\/molecules21070909","article-title":"New potential antimalarial\nagents: design, synthesis and biological evaluation of some novel\nquinoline derivatives as antimalarial agents","volume":"21","author":"Radini","year":"2016","journal-title":"Molecules"},{"key":"2026081811260139600_cit15","doi-asserted-by":"publisher","first-page":"65496","DOI":"10.1039\/C5RA08778C","article-title":"Antihypertensive\nactivity of a quinoline appended chalcone derivative and its site\nspecific binding interaction with a relevant target carrier protein","volume":"5","author":"Kumar","year":"2015","journal-title":"RSC Adv."},{"key":"2026081811260139600_cit16","doi-asserted-by":"publisher","first-page":"4333","DOI":"10.1080\/10406638.2022.2089177","article-title":"The versatile\nquinoline and its derivatives as anti-cancer agents: an overview","volume":"43","author":"Mathada","year":"2023","journal-title":"Polycycl. Aromat. Compd."},{"issue":"630","key":"2026081811260139600_cit17","first-page":"489","article-title":"Quinoline derivatives as tyrosine\nkinase inhibitors","volume":"6","author":"Crawley","year":"2003","journal-title":"U.S. Patent"},{"key":"2026081811260139600_cit18","doi-asserted-by":"publisher","first-page":"11","DOI":"10.3390\/ph16010011","article-title":"Synthesis and evaluation\nof novel S-alkyl phthalimide-and\nS-benzyl-oxadiazole-quinoline hybrids as inhibitors of monoamine oxidase\nand acetylcholinesterase","volume":"16","author":"Khan","year":"2023","journal-title":"Pharmaceuticals"},{"key":"2026081811260139600_cit19","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1016\/j.bmcl.2012.11.006","article-title":"Synthesis and antioxidant activities\nof 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives","volume":"23","author":"Zhang","year":"2013","journal-title":"Bioorg. Med. Ghem. Lett."},{"key":"2026081811260139600_cit20","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202300209","article-title":"Synthesis, Characterization, In Silico\nand In Vivo Evaluation of Benzimidazole-Bearing Quinoline Schiff Bases\nas New Anticonvulsant Agents","volume":"8","author":"Shabana","year":"2023","journal-title":"ChemistrySelect"},{"key":"2026081811260139600_cit21","doi-asserted-by":"publisher","first-page":"1197","DOI":"10.1080\/15257770802400081","article-title":"Synthesis and DNA binding studies\nof novel heterocyclic\nsubstituted quinoline schiff bases: a potent antimicrobial agent","volume":"27","author":"Lamani","year":"2008","journal-title":"Nucleosides, Nucleotides and Nucleic Acids"},{"key":"2026081811260139600_cit22","doi-asserted-by":"publisher","first-page":"27073","DOI":"10.1038\/s41598-024-78460-w","article-title":"Evaluating\nthe antidiabetes and antioxidant\nactivities of halogenated Schiff bases derived from 4-(diethylamino)\nsalicylaldehyde: in vitro antidiabetes, antioxidant and computational\ninvestigation","volume":"14","author":"Oladipo","year":"2024","journal-title":"Sci. Rep."},{"key":"2026081811260139600_cit23","doi-asserted-by":"publisher","first-page":"122447","DOI":"10.1016\/j.ica.2024.122447","article-title":"Exploring\nSchiff bases derived from 4-(diethylamino) salicylaldehyde and their\ncopper (II) complexes as antidiabetes and antioxidant agents: Structural\nelucidation, DFT computational and in vitro studies","volume":"575","author":"Oladipo","year":"2025","journal-title":"Inorg. Chim. Acta"},{"key":"2026081811260139600_cit24","doi-asserted-by":"publisher","DOI":"10.1016\/j.heliyon.2023.e23174","article-title":"Antidiabetes\nand antioxidant potential of Schiff bases derived from 2-naphthaldehye\nand substituted aromatic amines: Synthesis, crystal structure, Hirshfeld\nsurface analysis, computational, and invitro studies","volume":"10","author":"Oladipo","year":"2024","journal-title":"Heliyon"},{"key":"2026081811260139600_cit25","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202304967","article-title":"Synthesis\nand Therapeutic Potential of selected Schiff\nBases: In vitro Antibacterial, Antioxidant, Antidiabetic, and Computational\nStudies","volume":"9","author":"Adeleke","year":"2024","journal-title":"ChemistrySelect"},{"key":"2026081811260139600_cit26","doi-asserted-by":"publisher","first-page":"130620","DOI":"10.1016\/j.molstruc.2021.130620","article-title":"Synthesis,\ncrystal structure, Hirshfeld surface analysis and DFT studies of N-(2,\n6-diisopropylphenyl)-1-(4-methoxyphenyl) methanimine","volume":"1241","author":"Oladipo","year":"2021","journal-title":"J. Mol. Struct."},{"key":"2026081811260139600_cit27","doi-asserted-by":"publisher","first-page":"1863","DOI":"10.1134\/S1068162024050078","article-title":"Antidiabetic,\nAntidepressant, Antiparkinson\u2019s, Neuroprotective, and Antioxidant\nPotentials of Novel Schiff Base Derivatives of a Lichen Metabolite,\nUsnic Acid","volume":"50","author":"Yabo-Dambagi","year":"2024","journal-title":"Russ. J. Bioorg. Chem."},{"key":"2026081811260139600_cit28","doi-asserted-by":"publisher","first-page":"624","DOI":"10.1007\/s00044-020-02666-6","article-title":"Design, synthesis and\nbiological evaluation of Schiff\u2019s\nbase derivatives as multifunctional agents for the treatment of Alzheimer\u2019s\ndisease","volume":"30","author":"Shi","year":"2021","journal-title":"Med. Chem. Res."},{"key":"2026081811260139600_cit29","doi-asserted-by":"publisher","first-page":"60","DOI":"10.3390\/molecules23010060","article-title":"Synthesis\nand biological evaluation\nof new thiosemicarbazone derivative schiff bases as monoamine oxidase\ninhibitory agents","volume":"23","author":"C\u0327avus\u0327og\u0306lu","year":"2018","journal-title":"Molecules"},{"key":"2026081811260139600_cit30","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1016\/j.bioorg.2018.11.016","article-title":"Synthesis and biological evaluation\nof new pyrazolone Schiff bases as monoamine oxidase and cholinesterase\ninhibitors","volume":"84","author":"Tok","year":"2019","journal-title":"Bioorg. Chem."},{"key":"2026081811260139600_cit31","doi-asserted-by":"publisher","first-page":"18","DOI":"10.3390\/scipharm92020018","article-title":"Synthesis,\nBiological Evaluation,\nMolecular Docking and ADME Studies of Novel Pyrrole-Based Schiff Bases\nas Dual Acting MAO\/AChE Inhibitors","volume":"92","author":"Mateev","year":"2024","journal-title":"Scientia\nPharmaceutica"},{"key":"2026081811260139600_cit32","doi-asserted-by":"publisher","first-page":"4160","DOI":"10.3390\/molecules26144160","article-title":"Synthesis\nand bioinformatic characterization of new Schiff bases with possible\napplicability in brain disorders","volume":"26","author":"Avram","year":"2021","journal-title":"Molecules"},{"key":"2026081811260139600_cit33","doi-asserted-by":"publisher","first-page":"13276","DOI":"10.1039\/D4NJ01621A","article-title":"Copper (II) complexes derived from\nnaphthalene-based\nhalogenated Schiff bases: Synthesis, structural analysis, DFT computational\nstudies and in vitro biological activities","volume":"48","author":"Oladipo","year":"2024","journal-title":"New J. Chem."},{"key":"2026081811260139600_cit34","doi-asserted-by":"publisher","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short\nhistory of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A:\nFound. Crystallogr."},{"key":"2026081811260139600_cit35","doi-asserted-by":"publisher","first-page":"1141","DOI":"10.1107\/S1600576720007438","article-title":"X-Seed\n4: updates to a program for small-molecule supramolecular crystallography","volume":"53","author":"Barbour","year":"2020","journal-title":"J. Appl. Crystallogr."},{"key":"2026081811260139600_cit36","doi-asserted-by":"publisher","first-page":"5739","DOI":"10.1073\/pnas.0710626105","article-title":"Structure of human monoamine oxidase A at 2.2-\u00c5\nresolution: the control of opening the entry for substrates\/inhibitors","volume":"105","author":"Son","year":"2008","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"2026081811260139600_cit37","doi-asserted-by":"publisher","first-page":"12684","DOI":"10.1073\/pnas.0505975102","article-title":"Three-dimensional structure of human\nmonoamine oxidase A (MAO A): relation to the structures of rat MAO\nA and human MAO B","volume":"102","author":"De\nColibus","year":"2005","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"2026081811260139600_cit38","doi-asserted-by":"publisher","first-page":"681","DOI":"10.1007\/s10822-007-9133-z","article-title":"Epik: a software program for pK a\nprediction and protonation state generation for drug-like molecules","volume":"21","author":"Shelley","year":"2007","journal-title":"J. Comput. Aided mol. Des."},{"key":"2026081811260139600_cit39","doi-asserted-by":"publisher","first-page":"351","DOI":"10.1002\/prot.10613","article-title":"A hierarchical approach\nto all-atom\nprotein loop prediction","volume":"55","author":"Jacobson","year":"2004","journal-title":"Proteins: Struct. Funct.\nBioinf."},{"key":"2026081811260139600_cit40","doi-asserted-by":"publisher","first-page":"1739","DOI":"10.1021\/jm0306430","article-title":"Glide: a new approach\nfor rapid, accurate docking and scoring. 1. Method and assessment\nof docking accuracy","volume":"47","author":"Friesner","year":"2004","journal-title":"J. Med. Chem."},{"key":"2026081811260139600_cit41","doi-asserted-by":"publisher","first-page":"4","DOI":"10.1186\/s40203-014-0004-8","article-title":"Molecular dynamics simulations: from structure function\nrelationships to drug discovery","volume":"2","author":"Nair","year":"2014","journal-title":"Silico Pharmacol"},{"key":"2026081811260139600_cit42","doi-asserted-by":"publisher","first-page":"1157","DOI":"10.1002\/jcc.20035","article-title":"Development\nand testing of a general amber force field","volume":"25","author":"Wang","year":"2004","journal-title":"J. Computat. Chem."},{"key":"2026081811260139600_cit43","doi-asserted-by":"publisher","first-page":"523","DOI":"10.1002\/bip.360320508","article-title":"Langevin\ndynamics of peptides: The\nfrictional dependence of isomerization rates of N-acetylalanyl-N\u2032-methylamide","volume":"32","author":"Loncharich","year":"1992","journal-title":"Biopolymers"},{"key":"2026081811260139600_cit44","doi-asserted-by":"publisher","first-page":"1552","DOI":"10.1021\/ci500161d","article-title":"OriginPro\n9.1: scientific data analysis and graphing software-software review","volume":"54","author":"Seifert","year":"2014","journal-title":"J. Chem. Inf. Model."},{"issue":"18","key":"2026081811260139600_cit45","doi-asserted-by":"publisher","first-page":"1530010","DOI":"10.1142\/S0217979215300108","article-title":"Variational\nprinciple of Bogoliubov and generalized mean fields in many-particle\ninteracting systems","volume":"29","author":"Kuzemsky","year":"2015","journal-title":"Int. J. Mod. Phys. B"},{"key":"2026081811260139600_cit46","doi-asserted-by":"publisher","first-page":"2091","DOI":"10.1021\/jm5019093","article-title":"PAINS in the assay:\nchemical mechanisms of assay interference and promiscuous enzymatic\ninhibition observed during a sulfhydryl-scavenging HTS","volume":"58","author":"Dahlin","year":"2015","journal-title":"J. Med. Chem."},{"key":"2026081811260139600_cit47","doi-asserted-by":"publisher","first-page":"42717","DOI":"10.1038\/srep42717","article-title":"SwissADME: a free web tool to evaluate\npharmacokinetics, drug-likeness and medicinal chemistry friendliness\nof small molecules","volume":"7","author":"Daina","year":"2017","journal-title":"Sci. Rep."},{"key":"2026081811260139600_cit48","unstructured":"Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.\n          Gaussian 16.\nRev. C. 01: Wallingford, CT. Wallingford, CT, 2016."},{"key":"2026081811260139600_cit49","unstructured":"Dennington, R. D. I. I.; Keith, T. A.; Millam, J. M.\n          GaussView. version 6.0. 16; Semichem Inc Shawnee Mission KS, 2016."},{"key":"2026081811260139600_cit50","doi-asserted-by":"publisher","first-page":"1372","DOI":"10.1063\/1.464304","article-title":"A new mixing\nof Hartree\u2013Fock and local density-functional theories","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"2026081811260139600_cit51","doi-asserted-by":"publisher","first-page":"161103","DOI":"10.1063\/1.2126975","article-title":"Exchange-correlation\nfunctional with\nbroad accuracy for metallic and nonmetallic compounds, kinetics, and\nnoncovalent interactions","volume":"123","author":"Zhao","year":"2005","journal-title":"J. Chem. Phys."},{"key":"2026081811260139600_cit52","doi-asserted-by":"publisher","first-page":"12590","DOI":"10.1021\/jp408166m","article-title":"Performance of M06,\nM06\u20132X, and M06-HF density functionals for conformationally\nflexible anionic clusters: M06 functionals perform better than B3LYP\nfor a model system with dispersion and ionic hydrogen-bonding interactions","volume":"117","author":"Walker","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"2026081811260139600_cit53","doi-asserted-by":"publisher","first-page":"9113","DOI":"10.1063\/1.1413524","article-title":"Polarization\nconsistent basis sets: Principles","volume":"115","author":"Jensen","year":"2001","journal-title":"J. Chem.\nPhys."},{"key":"2026081811260139600_cit54","doi-asserted-by":"publisher","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal\nsolvation model based on\nsolute electron density and on a continuum model of the solvent defined\nby the bulk dielectric constant and atomic surface tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"2026081811260139600_cit55","unstructured":"Legault, C.\n          \n          CYLview, 1.0 b http:\/\/www.cylview.org:Universite\u0301deSherbrooke.Sherbrooke,QC.2009, Canada. Accessed (Jan 24, 2025)."},{"key":"2026081811260139600_cit56","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1601","article-title":"Molecular electrostatic potential\nanalysis: A powerful tool to interpret and predict chemical reactivity","volume":"12","author":"Suresh","year":"2022","journal-title":"Comput. Mol. Sci."},{"key":"2026081811260139600_cit57","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1016\/j.molstruc.2012.09.047","article-title":"Molecular orbital studies (hardness,\nchemical potential, electrophilicity, and first electron excitation),\nvibrational investigation and theoretical NBO analysis of 2-hydroxy-5-bromobenzaldehyde\nby density functional method","volume":"1031","author":"Nataraj","year":"2013","journal-title":"J. Mol. Struct."},{"key":"2026081811260139600_cit58","doi-asserted-by":"publisher","first-page":"160","DOI":"10.1016\/j.jorganchem.2018.03.036","article-title":"Computational\ninsights into the mechanisms of Ru-catalyzed\ncycloisomerization of 2-ethynylaniline and 2-(2-propynyl) tosylanilide:\nThe role of pyridine in assisting the metal-vinylidene formation","volume":"864","author":"Ogunlana","year":"2018","journal-title":"J. Organomet. Chem."},{"key":"2026081811260139600_cit59","doi-asserted-by":"publisher","first-page":"722","DOI":"10.1063\/1.1700523","article-title":"A molecular\norbital theory of reactivity\nin aromatic hydrocarbons","volume":"20","author":"Fukui","year":"1952","journal-title":"J. Chem. Phys."},{"key":"2026081811260139600_cit60","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1177\/1747519820932091","article-title":"Theoretical\ninvestigations on the HOMO\u2013LUMO gap and global reactivity descriptor\nstudies, natural bond orbital, and nucleus-independent chemical shifts\nanalyses of 3-phenylbenzo [d] thiazole-2 (3 H)-imine and its para-substituted\nderivatives: Solvent and substituent effects","volume":"45","author":"Miar","year":"2021","journal-title":"J. Chem. Res."},{"key":"2026081811260139600_cit61","doi-asserted-by":"publisher","first-page":"26076","DOI":"10.1021\/acsomega.2c00985","article-title":"Formamidine-based\nthiuram disulfides as efficient inhibitors of acid corrosion of mild\nsteel: electrochemical, surface, and density functional theory\/monte\ncarlo simulation studies","volume":"7","author":"Akpan","year":"2022","journal-title":"ACS omega"},{"key":"2026081811260139600_cit62","doi-asserted-by":"publisher","first-page":"4184","DOI":"10.1021\/jp0225774","article-title":"Ionization potential,\nelectron affinity,\nelectronegativity, hardness, and electron excitation energy: molecular\nproperties from density functional theory orbital energies","volume":"107","author":"Zhan","year":"2003","journal-title":"J. Phys. Chem. A"},{"key":"2026081811260139600_cit63","doi-asserted-by":"publisher","first-page":"139734","DOI":"10.1016\/j.molstruc.2024.139734","article-title":"Structural\nstudies, DFT computational analysis and\ninhibitory potential of (E)-N\u2019-(2-bromophenyl)-N-(2, 6-diisopropylphenyl)\nformamidine against CDK1 and CDK2","volume":"1320","author":"Oladipo","year":"2025","journal-title":"J. Mol. Struct."},{"key":"2026081811260139600_cit64","doi-asserted-by":"publisher","first-page":"55","DOI":"10.1007\/s44371-024-00059-x","article-title":"Quantum\nchemical investigation of the degradation of acid orange 7 by different\noxidants","volume":"1","author":"Badeji","year":"2024","journal-title":"Discovery Chem."},{"key":"2026081811260139600_cit65","doi-asserted-by":"publisher","first-page":"135","DOI":"10.4236\/jqis.2011.13019","article-title":"The electronegativity\nand the global hardness are periodic properties\nof atoms","volume":"01","author":"Islam","year":"2011","journal-title":"J. Quantum Inf. Sci."},{"key":"2026081811260139600_cit66","doi-asserted-by":"publisher","first-page":"5533","DOI":"10.1016\/j.bmc.2004.08.013","article-title":"Electrophilicity\nindex as a possible descriptor of biological activity","volume":"12","author":"Parthasarathi","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"2026081811260139600_cit67","doi-asserted-by":"publisher","first-page":"10068","DOI":"10.1021\/jp904674x","article-title":"Net electrophilicity","volume":"113","author":"Chattaraj","year":"2009","journal-title":"J. Phys. Chem. A"},{"issue":"19","key":"2026081811260139600_cit68","doi-asserted-by":"publisher","first-page":"5708","DOI":"10.1021\/ja00279a008","article-title":"The use of global\nand local molecular parameters for\nthe analysis of the gas-phase basicity of amines","volume":"108","author":"Yang","year":"1986","journal-title":"J. Am. Chem. Soc."},{"key":"2026081811260139600_cit69","doi-asserted-by":"publisher","first-page":"41","DOI":"10.21477\/ijapsr.3.4.1","article-title":"Aluminum corrosion\ninhibition by 7-(Ethylthiobenzimidazolyl) theophylline in 1M hydrochloric\nacid: experimental and DFT studies","volume":"3","author":"Diki","year":"2018","journal-title":"Int. J.\nAppl. Pharm. Sci. Res."},{"key":"2026081811260139600_cit70","doi-asserted-by":"publisher","first-page":"11247","DOI":"10.1039\/c8cp01249k","article-title":"The halogen\neffect on the 13 C NMR chemical shift in substituted benzenes","volume":"20","author":"V\nViesser","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026081811260139600_cit71","doi-asserted-by":"publisher","first-page":"2103","DOI":"10.46481\/jnsps.2024.2103","article-title":"Computational investigation\nand biological activity of selected Schiff bases","author":"Oladipo","year":"2024","journal-title":"J. Niger. Soc. Phys. Sci."},{"key":"2026081811260139600_cit72","doi-asserted-by":"publisher","first-page":"1037","DOI":"10.1515\/ncrs-2024-0279","article-title":"Crystal structure\nof a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene)\nbenzenaminium acetate\u2013 4-bromoaniline (1\/1). Z. fu\u0308r\nKrist","volume":"239","author":"Oladipo","year":"2024","journal-title":"New Cryst. Struct."},{"key":"2026081811260139600_cit73","first-page":"207","article-title":"Synthesis and anti-mycobacterium\nstudy of some fluorine containing Schiff bases of quinoline and their\nmetal complexes","volume":"7","author":"Mandewale","year":"2015","journal-title":"Der Pharm. Chem."},{"key":"2026081811260139600_cit74","doi-asserted-by":"publisher","first-page":"197","DOI":"10.1016\/j.ica.2013.02.029","article-title":"Imino-quinolyl\npalladium (II) and platinum (II) complexes:\nSynthesis, characterization, molecular structures and cytotoxic effect","volume":"400","author":"Motswainyana","year":"2013","journal-title":"Inorg. Chim. Acta"},{"key":"2026081811260139600_cit75","volume-title":"Cambridge\nInternational\nAS and A Level Chemistry Coursebook with CD-ROM","author":"Ryan","year":"2014"},{"key":"2026081811260139600_cit76","doi-asserted-by":"publisher","first-page":"103285","DOI":"10.1016\/j.arabjc.2021.103285","article-title":"Synthesis, characterization, anticancer\nand DNA photocleavage\nstudy of novel quinoline Schiff base and its metal complexes","volume":"14","author":"Patil","year":"2021","journal-title":"Arabian J. Chem."},{"key":"2026081811260139600_cit77","doi-asserted-by":"publisher","first-page":"687","DOI":"10.1080\/08927022.2022.2045016","article-title":"Structural\nbased investigation of novel pyrazole-thiazole Hybrids as dual CDK-1\nand CDK-2 inhibitors for cancer chemotherapy","volume":"48","author":"Obakachi","year":"2022","journal-title":"Mol. Simul."},{"key":"2026081811260139600_cit78","doi-asserted-by":"publisher","first-page":"80","DOI":"10.1007\/s40203-024-00250-z","article-title":"Exploring the therapeutic\npotential of prolinamides as multi-targeted agents for Alzheimer\u2019s\ndisease treatment: molecular docking and molecular dynamic simulation\nstudies","volume":"12","author":"Olalekan","year":"2024","journal-title":"Silico Pharmacol"},{"key":"2026081811260139600_cit79","doi-asserted-by":"publisher","first-page":"2626","DOI":"10.1021\/ci4002475","article-title":"MMGBSA\nas a tool to understand the\nbinding affinities of filamin\u2013peptide interactions","volume":"53","author":"Ylilauri","year":"2013","journal-title":"J. Chem. Inf. Model."},{"key":"2026081811260139600_cit80","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202200875","article-title":"Ligand-Guided Investigation of a\nSeries of Formamidine-Based Thiuram Disulfides as Potential Dual-Inhibitors\nof COX-1and COX-2","volume":"20","author":"Oladipo","year":"2023","journal-title":"Chem. Biodiversity"},{"key":"2026081811260139600_cit81","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1080\/07391102.2024.2323701","article-title":"Repurposing\nof SARS-CoV-2 compounds against Marburg Virus using MD simulation,\nmm\/GBSA, PCA analysis, and free energy landscape","author":"Kumar","year":"2024","journal-title":"J. Biomol. Struct. and Dyn."},{"key":"2026081811260139600_cit82","doi-asserted-by":"publisher","first-page":"164","DOI":"10.1186\/s43094-024-00722-1","article-title":"Computational\nand experimental insights\ninto glycyrrhizin-loaded nanostructured lipid carriers: docking, dynamics,\ndesign optimization, and anticancer efficacy in lung cancer cells","volume":"10","author":"Kumar","year":"2024","journal-title":"Future J. Pharm. Sci."},{"key":"2026081811260139600_cit83","doi-asserted-by":"publisher","first-page":"128553","DOI":"10.1016\/j.molstruc.2020.128553","article-title":"Formamidine-based\nthiuram disulfides: Synthesis, structural characterization, biological\nstudies, and preliminary cheminformatics evaluation","volume":"1219","author":"Oladipo","year":"2020","journal-title":"J. Mol. Struct."},{"key":"2026081811260139600_cit84","doi-asserted-by":"publisher","first-page":"204","DOI":"10.5155\/eurjchem.12.2.204-215.2088","article-title":"Synthesis, crystal\nstructure with free radical scavenging activity and theoretical studies\nof Schiff bases derived from 1-naphthylamine, 2, 6-diisopropylaniline,\nand substituted benzaldehyde","volume":"12","author":"Oladipo","year":"2021","journal-title":"Eur. J. Chem."},{"key":"2026081811260139600_cit85","doi-asserted-by":"publisher","first-page":"120316","DOI":"10.1016\/j.ica.2021.120316","article-title":"Ag (I) symmetrical\nN, N\u2032-diarylformamidine dithiocarbamate PPh3 complexes: Synthesis,\nstructural characterization, quantum chemical calculations and in\nvitro biological studies","volume":"520","author":"Oladipo","year":"2021","journal-title":"Inorg. Chim. Acta"},{"key":"2026081811260139600_cit86","doi-asserted-by":"publisher","first-page":"1959","DOI":"10.1021\/jp003458w","article-title":"Fukui indices\nfrom perturbed kohn\u2013 sham orbitals and regional softness from\nmayer atomic valences","volume":"105","author":"Mineva","year":"2001","journal-title":"J. Phys. Chem. A"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.4c11530","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/10\/25\/26500\/40838223\/ao4c11530.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/10\/25\/26500\/40838223\/ao4c11530.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T17:53:10Z","timestamp":1787075590000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/10\/25\/26500\/3654732\/Investigating-the-Inhibitory-Potential-of"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6,13]]},"references-count":86,"journal-issue":{"issue":"25","published-online":{"date-parts":[[2025,6,13]]},"published-print":{"date-parts":[[2025,7,1]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.4c11530","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,6,13]]}}}