{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,2]],"date-time":"2026-08-02T05:21:57Z","timestamp":1785648117780,"version":"3.56.0"},"reference-count":82,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2024,9,23]],"date-time":"2024-09-23T00:00:00Z","timestamp":1727049600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100009390","name":"Plovdiv University","doi-asserted-by":"publisher","award":["0000"],"award-info":[{"award-number":["0000"]}],"id":[{"id":"10.13039\/100009390","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009526","name":"Amrita Vishwa Vidyapeetham","doi-asserted-by":"publisher","award":["0000"],"award-info":[{"award-number":["0000"]}],"id":[{"id":"10.13039\/100009526","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004242","name":"Princess Nourah bint Abdulrahman University","doi-asserted-by":"publisher","award":["0000"],"award-info":[{"award-number":["0000"]}],"id":[{"id":"10.13039\/501100004242","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>A series of edaravone derivatives and the corresponding Cu(II) complexes were synthesized and characterized using spectroscopic and analytical techniques such as IR, UV, NMR and elemental analysis. Antioxidant activities of all compounds were examined using free radical scavenging methods such as hydrogen peroxide scavenging activity (HPSA), 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2-2\u2032-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS) assays. All of the tested compounds exhibited good antioxidant activity. Further, the frontier orbital energy levels, as well as various chemical properties, were determined using the density functional theory (DFT) calculations. The MEP maps of all of the derivatives were plotted to identify the nucleophilic and electrophilic reactive sites. Further, binding energies of all of the organic compounds with the protein tyrosinase was investigated to determine their potential anti-melanogenic applications. The selected ligand, L6 was subjected to molecular dynamics simulation analysis to determine the stability of the ligand\u2013protein complex. The MD simulation was performed (150 ns) to estimate the stability of the tyrosinase\u2013L6 complex. Other key parameters, such as, RMSD, RMSF, Rg, hydrogen bonds, SASA and MMPBSA were also analyzed to understand the interaction of L6 with the tyrosinase protein.<\/jats:p>","DOI":"10.3390\/antiox13091148","type":"journal-article","created":{"date-parts":[[2024,9,23]],"date-time":"2024-09-23T09:15:07Z","timestamp":1727082907000},"page":"1148","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis, Characterization and Assessment of Antioxidant and Melanogenic Inhibitory Properties of Edaravone Derivatives"],"prefix":"10.3390","volume":"13","author":[{"given":"R.","family":"Divya Mohan","sequence":"first","affiliation":[{"name":"Department of Chemistry, Amrita Vishwa Vidyapeetham, Amritapuri 690525, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S. A.","family":"Anaswara","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Amrita Vishwa Vidyapeetham, Amritapuri 690525, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4566-9384","authenticated-orcid":false,"given":"Naveen V.","family":"Kulkarni","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Amrita Vishwa Vidyapeetham, Amritapuri 690525, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6569-8348","authenticated-orcid":false,"given":"Dimitar G.","family":"Bojilov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen str., 4000 Plovdiv, Bulgaria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0314-6553","authenticated-orcid":false,"given":"Stanimir P.","family":"Manolov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen str., 4000 Plovdiv, Bulgaria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4662-3735","authenticated-orcid":false,"given":"Iliyan I.","family":"Ivanov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, University of Plovdiv, 24 Tzar Assen str., 4000 Plovdiv, Bulgaria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jamelah S.","family":"Al-Otaibi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Y.","family":"Sheena Mary","sequence":"additional","affiliation":[{"name":"Department of Physics, FMNC, University of Kerala, Kollam 691001, India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Bailly, C., Hecquet, P.-E., Kouach, M., Thuru, X., and Goossens, J.-F. (2020). Chemical Reactivity and Uses of 1-Phenyl-3-Methyl-5-Pyrazolone (PMP), Also Known as Edaravone. Bioorganic Med. Chem., 28.","DOI":"10.1016\/j.bmc.2020.115463"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Mohan, D., and Kulkarni, N. (2024). Recent Developments in the Design of Functional Derivatives of Edaravone and Exploration of Their Antioxidant Activities. Mol. Divers.","DOI":"10.1007\/s11030-024-10940-7"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1111\/j.1527-3466.2008.00041.x","article-title":"The Novel Antioxidant Edaravone: From Bench to Bedside","volume":"26","author":"Watanabe","year":"2008","journal-title":"Cardiovasc. Ther."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Yamashita, T., and Abe, K. (2024). Update on Antioxidant Therapy with Edaravone: Expanding Applications in Neurodegenerative Diseases. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25052945"},{"key":"ref_5","unstructured":"Canadian Agency for Drugs and Technologies in Health (2019). Pharmacoeconomic Review Report: Edaravone (Radicava): (Mitsubishi Tanabe Pharma Corporation): Indication: For the treatment of Amyotrophic Lateral Sclerosis (ALS) [Internet], Canadian Agency for Drugs and Technologies in Health."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3429","DOI":"10.1007\/s10072-023-06869-8","article-title":"Safety and Efficacy of Edaravone in Patients with Amyotrophic Lateral Sclerosis: A Systematic Review and Meta-Analysis","volume":"44","author":"Nourelden","year":"2023","journal-title":"Neurol. Sci."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Cho, H., and Shukla, S. (2020). Role of Edaravone as a Treatment Option for Patients with Amyotrophic Lateral Sclerosis. Pharmaceuticals, 14.","DOI":"10.3390\/ph14010029"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"105967","DOI":"10.1016\/j.intimp.2019.105967","article-title":"Potential Use of Edaravone to Reduce Specific Side Effects of Chemo-, Radio- and Immuno-Therapy of Cancers","volume":"77","author":"Bailly","year":"2019","journal-title":"Int. Immunopharmacol."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Cha, S.J., and Kim, K. (2022). Effects of the Edaravone, a Drug Approved for the Treatment of Amyotrophic Lateral Sclerosis, on Mitochondrial Function and Neuroprotection. Antioxidants, 11.","DOI":"10.3390\/antiox11020195"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"907","DOI":"10.1111\/jcpt.13392","article-title":"Clinical Effects and Safety of Edaravone in Treatment of Acute Ischaemic Stroke: A Meta-analysis of Randomized Controlled Trials","volume":"46","author":"Chen","year":"2021","journal-title":"J. Clin. Pharm. Ther."},{"key":"ref_11","first-page":"e25960","article-title":"Ethnical Disparities in Response to Edaravone in Patients With Amyotrophic Lateral Sclerosis","volume":"14","author":"Jayasinghe","year":"2022","journal-title":"Cur\u0113us"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Rahim, M., Madi, F., Nouar, L., Haiahem, S., Fateh, D., and Khatmi, D. (2014). \u03b2-Cyclodextrin Interaction with Edaravone: Molecular Modeling Study. Advances in Quantum Chemistry, Academic Press.","DOI":"10.1016\/B978-0-12-800536-1.00014-9"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1180","DOI":"10.1021\/jp209930y","article-title":"On the Outstanding Antioxidant Capacity of Edaravone Derivatives through Single Electron Transfer Reactions","volume":"116","author":"Galano","year":"2012","journal-title":"J. Phys. Chem. B"},{"key":"ref_14","first-page":"610","article-title":"Antioxidant and Acetylcholinesterase Inhibition Activity of Aliphatic and Aromatic Edaravone Derivatives","volume":"30","author":"Rivero","year":"2020","journal-title":"Med. Chem. Res."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Minnelli, C., Laudadio, E., Galeazzi, R., Rusciano, D., Armeni, T., Stipa, P., Cantarini, M., and Mobbili, G. (2019). Synthesis, Characterization and Antioxidant Properties of a New Lipophilic Derivative of Edaravone. Antioxidants, 8.","DOI":"10.3390\/antiox8080258"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2562","DOI":"10.1016\/j.bmcl.2016.03.024","article-title":"Synthesis, Molecular Properties Prediction and Anticancer, Antioxidant Evaluation of New Edaravone Derivatives","volume":"26","author":"Polkam","year":"2016","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"133044","DOI":"10.1016\/j.molstruc.2022.133044","article-title":"A Critical Review on Recent Trends on Pharmacological Applications of Pyrazolone Endowed Derivatives","volume":"1262","author":"Mustafa","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Minnelli, C., Laudadio, E., Fiorini, R., Galeazzi, R., Armeni, T., Stipa, P., Rusciano, D., and Mobbili, G. (2022). Influence of a Lipophilic Edaravone on Physical State and Activity of Antioxidant Liposomes: An Experimental and in Silico Study. Colloids Surf. B Biointerfaces, 210.","DOI":"10.1016\/j.colsurfb.2021.112217"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5784","DOI":"10.1039\/D2OB01143C","article-title":"Salt Effects on Mixed Composition Membranes Containing an Antioxidant Lipophilic Edaravone Derivative: A Computational-Experimental Study","volume":"20","author":"Laudadio","year":"2022","journal-title":"Org. Biomol. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3535","DOI":"10.1016\/j.bmcl.2015.06.090","article-title":"Novel Hybrids of 3-n-Butylphthalide and Edaravone: Design, Synthesis and Evaluations as Potential Anti-Ischemic Stroke Agents","volume":"25","author":"Sheng","year":"2015","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.bbrc.2021.03.171","article-title":"Design, Synthesis, and Neuroprotective Effects of Novel Hybrid Compounds Containing Edaravone Analogue and 3-n-Butylphthalide Ring-Opened Derivatives","volume":"556","author":"Li","year":"2021","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"718","DOI":"10.1016\/j.bmcl.2017.01.050","article-title":"DL -3- n -Butylphthalide-Edaravone Hybrids as Novel Dual Inhibitors of Amyloid- \u03b2 Aggregation and Monoamine Oxidases with High Antioxidant Potency for Alzheimer\u2019s Therapy","volume":"27","author":"Qiang","year":"2017","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1038\/aps.2015.31","article-title":"The Edaravone and 3-n-Butylphthalide Ring-Opening Derivative 10b Effectively Attenuates Cerebral Ischemia Injury in Rats","volume":"36","author":"Hua","year":"2015","journal-title":"Acta Pharmacol. Sin."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Jia, J., Wu, J., Ji, D., Jiao, W., Wang, X., Huang, Z., and Zhang, Y. (2022). Synthesis and Biological Evaluation of Hybrids from Optically Active Ring-Opened 3-N-Butylphthalide Derivatives and 4-Fluro-Edaravone as Potential Anti-Acute Ischemic Stroke Agents. Bioorganic Med. Chem., 69.","DOI":"10.1016\/j.bmc.2022.116891"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"e01438","DOI":"10.1002\/brb3.1438","article-title":"Human Urinary Kallidinogenase or Edaravone Combined with Butylphthalide in the Treatment of Acute Ischemic Stroke","volume":"9","author":"Qian","year":"2019","journal-title":"Brain Behav."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3892\/mmr.2021.12490","article-title":"Protective Multi-target Effects of DL-3-n-butylphthalide Combined with 3-methyl-1-phenyl-2-pyrazolin-5-one in Mice with Ischemic Stroke","volume":"24","author":"Guan","year":"2021","journal-title":"Mol. Med. Rep."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Lapshina, M.A., Shevtsova, E.F., Grigoriev, V.V., Aksinenko, A.Y., Ustyugov, A.A., Steinberg, D.A., Maleev, G.V., Dubrovskaya, E.S., Goreva, T.V., and Epishina, T.A. (2023). New Adamantane-Containing Edaravone Conjugates as Potential Neuroprotective Agents for ALS Treatments. Molecules, 28.","DOI":"10.3390\/molecules28227567"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1596","DOI":"10.1080\/14756366.2020.1801673","article-title":"Design, Synthesis and Biological Evaluation of Edaravone Derivatives Bearing the N-Benzyl Pyridinium Moiety as Multifunctional Anti-Alzheimer\u2019s Agents","volume":"35","author":"Zondagh","year":"2020","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Thawabteh, A.M., Jibreen, A., Karaman, D., Thawabteh, A., and Karaman, R. (2023). Skin Pigmentation Types, Causes and Treatment\u2014A Review. Molecules, 28.","DOI":"10.20944\/preprints202305.0751.v1"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7395","DOI":"10.1021\/acs.jmedchem.7b00967","article-title":"Inhibitors of Melanogenesis: An Updated Review","volume":"61","author":"Pillaiyar","year":"2018","journal-title":"J. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Maddaleno, A.S., Camargo, J., Mitjans, M., and Vinardell, M.P. (2021). Melanogenesis and Melasma Treatment. Cosmetics, 8.","DOI":"10.3390\/cosmetics8030082"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1111\/j.1468-2494.2010.00616.x","article-title":"The Melanogenesis and Mechanisms of Skin-lightening Agents\u2014Existing and New Approaches","volume":"33","author":"Gillbro","year":"2011","journal-title":"Int. J. Cosmet. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"163","DOI":"10.4103\/2225-4110.113443","article-title":"Evaluation of the Antioxidant and Melanogenesis Inhibitory Properties of Pracparatum Mungo (Lu-Do Huang)","volume":"3","author":"Kao","year":"2013","journal-title":"J. Tradit. Complement. Med."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"115655","DOI":"10.1016\/j.ejmech.2023.115655","article-title":"Recent Advances in Triazoles as Tyrosinase Inhibitors","volume":"259","author":"Mermer","year":"2023","journal-title":"Eur. J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1512","DOI":"10.1038\/jid.2014.65","article-title":"Melanocytes as Instigators and Victims of Oxidative Stress","volume":"134","author":"Denat","year":"2014","journal-title":"J. Investig. Dermatol."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Upadhyay, P.R., Starner, R.J., Swope, V.B., Wakamatsu, K., Ito, S., and Abdel-Malek, Z.A. (2022). Differential Induction of Reactive Oxygen Species and Expression of Antioxidant Enzymes in Human Melanocytes Correlate with Melanin Content: Implications on the Response to Solar UV and Melanoma Susceptibility. Antioxidants, 11.","DOI":"10.3390\/antiox11061204"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"438","DOI":"10.1111\/pcmr.13165","article-title":"The Metabolism of Melanin Synthesis\u2014From Melanocytes to Melanoma","volume":"37","author":"Snyman","year":"2024","journal-title":"Pigment. Cell Melanoma Res."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Samsonowicz, M., Kalinowska, M., and Gryko, K. (2021). Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study. Materials, 14.","DOI":"10.3390\/ma14020264"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"9076","DOI":"10.1021\/acsomega.3c07885","article-title":"Theoretical Exploration of Enhanced Antioxidant Activity in Copper Complexes of Tetrahydroxystilbenes: Insights into Mechanisms and Molecular Interactions","volume":"9","author":"Hamadouche","year":"2024","journal-title":"ACS Omega"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Rodr\u00edguez-Arce, E., and Sald\u00edas, M. (2021). Antioxidant Properties of Flavonoid Metal Complexes and Their Potential Inclusion in the Development of Novel Strategies for the Treatment against Neurodegenerative Diseases. Biomed. Pharmacother., 143.","DOI":"10.1016\/j.biopha.2021.112236"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"El-Lateef, H.M.A., El-Dabea, T., Khalaf, M.M., and Abu-Dief, A.M. (2023). Recent Overview of Potent Antioxidant Activity of Coordination Compounds. Antioxidants, 12.","DOI":"10.3390\/antiox12020213"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"8351","DOI":"10.1021\/jo101589h","article-title":"Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants","volume":"75","author":"Williams","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_43","unstructured":"Vogel, A.I. (1966). A Textbook of Quantitative Inorganic Analysis, John Wiley & Sons Inc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1093\/carcin\/10.6.1003","article-title":"Prevention of Cytotoxicity and Inhibition of Intercellular Communication by Antioxidant Catechins Isolated from Chinese Green Tea","volume":"10","author":"Ruch","year":"1989","journal-title":"Carcinogenesis"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Manolov, S., Ivanov, I., and Bojilov, D. (2022). Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation. Molbank, 2022.","DOI":"10.3390\/M1350"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1080\/14786419.2014.902947","article-title":"Flavonoid Content and Radical Scavenging Potential of Extracts Prepared from Tobacco Cultivars and Waste","volume":"28","author":"Docheva","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1016\/S0891-5849(98)00315-3","article-title":"Antioxidant Activity Applying an Improved ABTS Radical Cation Decolorization Assay","volume":"26","author":"Re","year":"1999","journal-title":"Free. Radic. Biol. Med."},{"key":"ref_48","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., and Nakatsuji, H. (2016). Gaussian 16, Revision A.03, Gaussian, Inc."},{"key":"ref_49","unstructured":"Dennington, R., Keith, T.A., and Millam, J.M. (2016). GaussView, Version 6.1, Semichem Inc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"120111","DOI":"10.1016\/j.molliq.2022.120111","article-title":"Computational Study of Pd\u2013Cd Bimetallic Crystals: Spectroscopic Properties, Hirshfeld Surface Analysis, Non-Covalent Interaction, and Sensor Activity","volume":"365","author":"Ullah","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading","volume":"31","author":"Trott","year":"2009","journal-title":"J. Comput. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1016\/j.jmb.2010.10.048","article-title":"First Structures of an Active Bacterial Tyrosinase Reveal Copper Plasticity","volume":"405","author":"Sendovski","year":"2011","journal-title":"J. Mol. Biol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1107\/S0907444904011679","article-title":"PRODRG: A Tool for High-Throughput Crystallography of Protein\u2013Ligand Complexes","volume":"60","year":"2004","journal-title":"Acta Crystallogr. Sect. D Biol. Crystallogr."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"115652","DOI":"10.1016\/j.molliq.2021.115652","article-title":"Theoretical Investigation on the Reactive and Interaction Properties of Sorafenib\u2014DFT, AIM, Spectroscopic and Hirshfeld Analysis, Docking and Dynamics Simulation","volume":"330","author":"Mary","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4618","DOI":"10.1080\/07391102.2020.1779129","article-title":"In Silicoidentification of Potential Inhibitors fromCinnamonagainst Main Protease and Spike Glycoprotein of SARS CoV-2","volume":"39","author":"Prasanth","year":"2020","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1951","DOI":"10.1021\/ci500020m","article-title":"G_mmpbsa\u2014A GROMACS Tool for High-Throughput MM-PBSA Calculations","volume":"54","author":"Kumari","year":"2014","journal-title":"J. Chem. Inf. Model."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1515\/znb-2018-0117","article-title":"Synthesis, Characterization, and Electrochemical Study of a Mononuclear Cu(II) Complex with a 4-Acyl Pyrazolone Ligand","volume":"73","author":"Nakum","year":"2018","journal-title":"Z. F\u00fcr Naturforschung B"},{"key":"ref_58","first-page":"3069","article-title":"Synthesis, Characterization of Some Metal Complexes of 4-Acetylsemicarbazone-1-Phenyl-3-Methyl-2-Pyrazolin-5-One","volume":"22","author":"Patel","year":"2010","journal-title":"Asian J. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1039\/C9QO01174A","article-title":"K2S2O8-Promoted Direct Thiocyanation of Pyrazolin-5-Ones with Ammonium Thiocyanate at Room Temperature","volume":"7","author":"Mao","year":"2020","journal-title":"Org. Chem. Front."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2099","DOI":"10.13005\/ojc\/310430","article-title":"Synthesis of Some Pyrazolone Derivatives and Evaluation of Its Antibacterial and Cytotoxic Activity","volume":"31","author":"Prajuli","year":"2015","journal-title":"Orient. J. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"129344","DOI":"10.1016\/j.molstruc.2020.129344","article-title":"Synthesis and Structure of Mono and Bis {1,3-Bis(2- Pyridylimino)Isoindoline} Supported 3d Transition Metal Complexes","volume":"1226","author":"Reshma","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"133512","DOI":"10.1016\/j.molstruc.2022.133512","article-title":"Synthesis and Characterization of a Series of Cobalt Complexes: Investigation of Their Efficacy as Sensitizers in Dye-Sensitized Solar Cell Applications","volume":"1266","author":"Hegde","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"132018","DOI":"10.1016\/j.molstruc.2021.132018","article-title":"First Row Transition Metal Complexes of Bis(3,5-Dimethyl Pyrazolyl)Methane: Synthesis, Molecular Structure and Antibacterial Properties","volume":"1251","author":"Swathy","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Hegde, V., Sreekala, C.O., Kulkarni, N.V., and Mathew, J. (2024). Bis(Pyrazolyl)Methane Supported Cobalt (II) Complexes as Sensitizers in Dye-Sensitized Solar Cells. J. Photochem. Photobiology. A Chem., 449.","DOI":"10.1016\/j.jphotochem.2023.115389"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1007\/s00044-011-9576-6","article-title":"Transition Metal Complexes of Thiosemicarbazones with Quinoxaline Hub: An Emphasis on Antidiabetic Property","volume":"21","author":"Kulkarni","year":"2011","journal-title":"Med. Chem. Res."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1016\/j.molstruc.2011.10.008","article-title":"Pyrazole Bridged Binuclear Transition Metal Complexes: Synthesis, Characterization, Antimicrobial Activity and DNA Binding\/Cleavage Studies","volume":"1006","author":"Kulkarni","year":"2011","journal-title":"J. Mol. Struct."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"115647","DOI":"10.1016\/j.poly.2021.115647","article-title":"Interplay of the Intermolecular and Intramolecular Interactions in Stabilizing the Thione-Based Copper(I) Complexes and Their Significance in Protecting the Biomolecules against Metal-Mediated Oxidative Damage","volume":"215","author":"Chalana","year":"2022","journal-title":"Polyhedron"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"6625","DOI":"10.1021\/jp912001c","article-title":"Mechanism of the OH Radical Scavenging Activity of Nordihydroguaiaretic Acid: A Combined Theoretical and Experimental Study","volume":"114","author":"Galano","year":"2010","journal-title":"J. Phys. Chem. B"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"4290","DOI":"10.1021\/jf0502698","article-title":"Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary Supplements","volume":"53","author":"Prior","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4583","DOI":"10.1021\/ol048015f","article-title":"Reducing Activity of Polyphenols with Stable Radicals of the TTM Series. Electron Transfer versus H-Abstraction Reactions in Flavan-3-Ols","volume":"6","author":"Selga","year":"2004","journal-title":"Org. Lett."},{"key":"ref_71","doi-asserted-by":"crossref","unstructured":"Halliwell, B., and Gutteridge, J.M. (1985). Free Radicals in Biology and Medicine, Oxford University Press.","DOI":"10.1016\/0748-5514(85)90140-0"},{"key":"ref_72","first-page":"3227","article-title":"Characterization of in Vitro Antioxidant Potential ofAzadirachta Indica and Abutilon Indicum by Different Assay Methods","volume":"5","author":"Ravichandran","year":"2012","journal-title":"J. Pharm. Res."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Cano, A., Maestre, A.B., Hern\u00e1ndez-Ruiz, J., and Arnao, M.B. (2023). ABTS\/TAC Methodology: Main Milestones and Recent Applications. Processes, 11.","DOI":"10.3390\/pr11010185"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1084","DOI":"10.1021\/jp053641v","article-title":"Careful Scrutiny of the Philicity Concept","volume":"110","author":"Roy","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2785","DOI":"10.1002\/jcc.21256","article-title":"AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility","volume":"30","author":"Morris","year":"2009","journal-title":"J. Comput. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"3284","DOI":"10.1021\/ci500467k","article-title":"iLOGP: A Simple, Robust, and Efficient Description of n-Octanol\/Water Partition Coefficient for Drug Design Using the GB\/SA Approach","volume":"54","author":"Daina","year":"2014","journal-title":"J. Chem. Inf. Model."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1080\/14756366.2018.1545767","article-title":"A Comprehensive Review on Tyrosinase Inhibitors","volume":"34","author":"Zolghadri","year":"2019","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1002\/jssc.200700414","article-title":"Environmentally Friendly LC for the Simultaneous Determination of Ascorbic Acid and Its Derivatives in Skin-whitening Cosmetics","volume":"31","author":"Balaguer","year":"2008","journal-title":"J. Sep. Sci."},{"key":"ref_79","first-page":"4522","article-title":"DFT and MD Investigations of the Biomolecules of Phenothiazine Derivatives: Interactions with Gold and Water Molecules and Investigations in Search of Effective Drug for SARS-CoV-2","volume":"41","author":"Mary","year":"2022","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"131074","DOI":"10.1016\/j.molstruc.2021.131074","article-title":"Structural and Reactivity Studies of Pravadoline \u2013An Ionic Liquid, with Reference to Its Wavefunction-Relative Properties Using DFT and MD Simulation","volume":"1245","author":"Mary","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"116192","DOI":"10.1016\/j.molliq.2021.116192","article-title":"Stability and Reactivity Study of Bio-Molecules Brucine and Colchicine towards Electrophile and Nucleophile Attacks: Insight from DFT and MD Simulations","volume":"335","author":"Mary","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"130397","DOI":"10.1016\/j.molstruc.2021.130397","article-title":"Modeling the DFT Structural and Reactivity Studies of a Pyrimidine -6-Carboxylate Derivative with Reference to Its Wavefunction-Dependent, MD Simulations and Evaluation for Potential Antimicrobial Activity","volume":"1237","author":"Smitha","year":"2021","journal-title":"J. Mol. Struct."}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/13\/9\/1148\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:00:36Z","timestamp":1760112036000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/13\/9\/1148"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9,23]]},"references-count":82,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2024,9]]}},"alternative-id":["antiox13091148"],"URL":"https:\/\/doi.org\/10.3390\/antiox13091148","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,9,23]]}}}