{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,24]],"date-time":"2026-04-24T14:36:20Z","timestamp":1777041380789,"version":"3.51.4"},"reference-count":69,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2026,4,17]],"date-time":"2026-04-17T00:00:00Z","timestamp":1776384000000},"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>Oxidative stress and inflammation are interconnected pathological processes involved in the progression of neurodegenerative, cardiovascular, and metabolic diseases, highlighting the need for multifunctional therapeutic agents targeting multiple pathways. In this study, two novel hybrid compounds were designed and synthesized in three steps by conjugating butylated phenolic moieties derived from butylated hydroxytoluene and p-coumaric acid with proline and \u03b3-aminobutyric acid (GABA). The aim was the combination of antioxidant, anti-inflammatory, and cytoprotective properties within a single molecular framework. The compounds were evaluated using a comprehensive panel of in vitro and in vivo assays to assess antioxidant, metal-reducing, iron-chelating, antiglycation, anti-inflammatory, and acetylcholinesterase inhibitory activities. Both compounds exhibited significant antioxidant activity, with compound 2 demonstrating superior radical scavenging ability against DPPH, ABTS\u00b7+ and hydrogen peroxide (IC50 86 \u03bcM, 25 \u03bcM and 104 \u03bcM, respectively), enhanced ferric-reducing capacity (up to 91% of trolox activity), and strong iron-chelating activity (61.3%). Compound 2 also showed potent inhibition of lipid peroxidation (IC50 17.5 \u03bcM) and moderate antiglycation effects (44%), indicating substantial cytoprotective potential. Furthermore, both compounds selectively inhibited COX-2 over COX-1 and demonstrated moderate lipoxygenase inhibition, while compound 2 exhibited significant in vivo anti-inflammatory activity (53%), exceeding that of ibuprofen. Moderate acetylcholinesterase inhibition was also observed. In summary, the results confirm the design rationale, indicating that compound 2 could be further optimized as a multi-targeting molecule directed against oxidative stress- and inflammation-mediated conditions.<\/jats:p>","DOI":"10.3390\/molecules31081323","type":"journal-article","created":{"date-parts":[[2026,4,17]],"date-time":"2026-04-17T14:24:51Z","timestamp":1776435891000},"page":"1323","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Butylated Hydroxytoluene (BHT) and p-Coumaric Acid Conjugates of Dipeptide Proline and GABA as Multi-Functional Agents with High Pharmacological Potential"],"prefix":"10.3390","volume":"31","author":[{"given":"Georgios","family":"Papagiouvannis","sequence":"first","affiliation":[{"name":"Department of Pharmacy, School of Health Sciences, Frederick University, Nicosia 1036, Cyprus"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Panagiotis","family":"Theodosis-Nobelos","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, School of Health Sciences, Frederick University, Nicosia 1036, Cyprus"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eleni A.","family":"Rekka","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,4,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Krishnamurthy, H.K., Pereira, M., Rajavelu, I., Jayaraman, V., Krishna, K., Wang, T., Bei, K., and Rajasekaran, J.J. (2024). Oxidative stress: Fundamentals and advances in quantification techniques. Front. Chem., 12.","DOI":"10.3389\/fchem.2024.1470458"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1126","DOI":"10.1089\/ars.2012.5149","article-title":"Reactive oxygen species in inflammation and tissue injury","volume":"20","author":"Mittal","year":"2014","journal-title":"Antioxid. Redox Signal."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"122007","DOI":"10.1016\/j.lfs.2023.122007","article-title":"The crosstalk between Nrf2 and NF-\u03baB pathways in coronary artery disease: Can it be regulated by SIRT6?","volume":"330","author":"Casper","year":"2023","journal-title":"Life Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1603","DOI":"10.1016\/j.freeradbiomed.2010.09.006","article-title":"Oxidative stress, inflammation, and cancer: How are they linked?","volume":"49","author":"Reuter","year":"2010","journal-title":"Free Radic. Biol. Med."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1186\/1756-8722-6-19","article-title":"Targeting mitochondrial reactive oxygen species as novel therapy for inflammatory diseases and cancers","volume":"6","author":"Li","year":"2013","journal-title":"J. Hematol. Oncol."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Dubsky, M., Veleba, J., Sojakova, D., Marhefkova, N., Fejfarova, V., and Jude, E.B. (2023). Endothelial Dysfunction in Diabetes Mellitus: New Insights. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241310705"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2321","DOI":"10.1016\/j.devcel.2022.09.002","article-title":"Competition for endothelial cell polarity drives vascular morphogenesis in the mouse retina","volume":"57","author":"Barbacena","year":"2022","journal-title":"Dev. Cell"},{"key":"ref_8","first-page":"4838","article-title":"Relationship between lipid profile, inflammatory and endothelial dysfunction biomarkers, and type 1 diabetes mellitus: A case-control study","volume":"14","author":"Alkaabi","year":"2022","journal-title":"Am. J. Transl. Res."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Corpas, F.J., R\u00edo, L.A.D., and Palma, J.M. (2019). Impact of Nitric Oxide (NO) on the ROS Metabolism of Peroxisomes. Plants, 8.","DOI":"10.3390\/plants8020037"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"313","DOI":"10.2337\/dbi22-0036","article-title":"Cardiac Microvascular Dysfunction and Cardiomyopathy in Diabetes: Is Ferroptosis a Therapeutic Target?","volume":"72","author":"Liu","year":"2023","journal-title":"Diabetes"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1186\/s12933-025-02600-3","article-title":"The protective role of SGLT2 inhibitors on aortic aneurysm mediated by oxidative stress and inflammation in type 2 diabetes mellitus","volume":"24","author":"Zheng","year":"2025","journal-title":"Cardiovasc. Diabetol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1221","DOI":"10.1021\/acs.chemrev.8b00138","article-title":"Development of Multifunctional Molecules as Potential Therapeutic Candidates for Alzheimer\u2019s Disease, Parkinson\u2019s Disease, and Amyotrophic Lateral Sclerosis in the Last Decade","volume":"119","author":"Savelieff","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"880","DOI":"10.1017\/S1041610224000085","article-title":"Efficacy and safety of transcranial magnetic stimulation on cognition in mild cognitive impairment, Alzheimer\u2019s disease, Alzheimer\u2019s disease-related dementias, and other cognitive disorders: A systematic review and meta-analysis","volume":"36","author":"Pagali","year":"2024","journal-title":"Int. Psychogeriatr."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Misrani, A., Tabassum, S., and Yang, L. (2021). Mitochondrial Dysfunction and Oxidative Stress in Alzheimer\u2019s Disease. Front. Aging Neurosci., 13.","DOI":"10.3389\/fnagi.2021.617588"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"988","DOI":"10.1021\/acschemneuro.7b00410","article-title":"Advanced Glycation End Products Modulate Amyloidogenic APP Processing and Tau Phosphorylation: A Mechanistic Link between Glycation and the Development of Alzheimer\u2019s Disease","volume":"9","author":"Batkulwar","year":"2018","journal-title":"ACS Chem. Neurosci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1007\/s12035-014-9053-6","article-title":"Mechanism of Oxidative Stress and Synapse Dysfunction in the Pathogenesis of Alzheimer\u2019s Disease: Understanding the Therapeutics Strategies","volume":"53","author":"Kamat","year":"2016","journal-title":"Mol. Neurobiol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1251","DOI":"10.2174\/1381612826666200113162641","article-title":"Excitotoxicity as a Target Against Neurodegenerative Processes","volume":"26","author":"Binvignat","year":"2020","journal-title":"Curr. Pharm. Des."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Hemonnot, A.L., Hua, J., Ulmann, L., and Hirbec, H. (2019). Microglia in Alzheimer Disease: Well-Known Targets and New Opportunities. Front. Aging Neurosci., 11.","DOI":"10.3389\/fnagi.2019.00233"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1016\/j.bbi.2021.08.234","article-title":"Elevated \u03b2-secretase 1 expression mediates CD4+ T cell dysfunction via PGE2 signalling in Alzheimer\u2019s disease","volume":"98","author":"Dai","year":"2021","journal-title":"Brain Behav. Immun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"885","DOI":"10.2174\/1570159X18666200924122732","article-title":"Inflammation Drives Alzheimer\u2019s Disease: Emphasis on 5-lipoxygenase Pathways","volume":"19","author":"Siddiqui","year":"2021","journal-title":"Curr. Neuropharmacol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1917","DOI":"10.1093\/brain\/awy132","article-title":"The cholinergic system in the pathophysiology and treatment of Alzheimer\u2019s disease","volume":"141","author":"Hampel","year":"2018","journal-title":"Brain"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"108352","DOI":"10.1016\/j.neuropharm.2020.108352","article-title":"Efficacy of acetylcholinesterase inhibitors in Alzheimer\u2019s disease","volume":"190","author":"Marucci","year":"2021","journal-title":"Neuropharmacology"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1515\/revneuro-2019-0089","article-title":"Amyloid-\u03b2, tau, and the cholinergic system in Alzheimer\u2019s disease: Seeking direction in a tangle of clues","volume":"31","author":"Majdi","year":"2020","journal-title":"Rev. Neurosci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1016\/j.pnpbp.2010.07.032","article-title":"Cyclooxygenases and 5-lipoxygenase in Alzheimer\u2019s disease","volume":"35","author":"Manev","year":"2011","journal-title":"Prog. Neuropsychopharmacol. Biol. Psychiatry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9895","DOI":"10.1007\/s11033-020-06033-x","article-title":"Exploring the molecular approach of COX and LOX in Alzheimer\u2019s and Parkinson\u2019s disorder","volume":"47","author":"Kumar","year":"2020","journal-title":"Mol. Biol. Rep."},{"key":"ref_26","first-page":"269","article-title":"Inhibition of 5-lipoxygenase by zileuton in a rat model of myocardial infarction","volume":"17","author":"Abueid","year":"2017","journal-title":"Anatol. J. Cardiol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"488","DOI":"10.1124\/jpet.107.127035","article-title":"Cyclooxygenase inhibition limits blood-brain barrier disruption following intracerebral injection of tumor necrosis factor-alpha in the rat","volume":"323","author":"Taheri","year":"2007","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Song, W.J., Yun, J.H., Jeong, M.S., Kim, K.N., Shin, T., Kim, H.C., and Wie, M.B. (2021). Inhibitors of Lipoxygenase and Cyclooxygenase-2 Attenuate Trimethyltin-Induced Neurotoxicity through Regulating Oxidative Stress and Pro-Inflammatory Cytokines in Human Neuroblastoma SH-SY5Y Cells. Brain Sci., 11.","DOI":"10.3390\/brainsci11091116"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"192","DOI":"10.1007\/s12017-015-8351-0","article-title":"A dual inhibitor of cyclooxygenase and 5-lipoxygenase protects against kainic acid-induced brain injury","volume":"17","author":"Minutoli","year":"2015","journal-title":"NeuroMol. Med."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/j.ejmech.2015.06.026","article-title":"Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): A review","volume":"101","author":"Yehye","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Faraji, P., Borchert, A., Ahmadian, S., and Kuhn, H. (2024). Butylated Hydroxytoluene (BHT) Protects SH-SY5Y Neuroblastoma Cells from Ferroptotic Cell Death: Insights from In Vitro and In Vivo Studies. Antioxidants, 13.","DOI":"10.3390\/antiox13020242"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"204","DOI":"10.1186\/s10020-024-00980-y","article-title":"Oral administration of butylated hydroxytoluene induces neuroprotection in a streptozotocin-induced rat Alzheimer\u2019s disease model via inhibition of neuronal ferroptosis","volume":"30","author":"Faraji","year":"2024","journal-title":"Mol. Med."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"e13276","DOI":"10.1111\/jfbc.13276","article-title":"Antioxidant properties of eugenol, butylated hydroxylanisole, and butylated hydroxyl toluene with key biomolecules relevant to Alzheimer\u2019s diseases-In vitro","volume":"45","author":"Adefegha","year":"2021","journal-title":"J. Food Biochem."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Papagiouvannis, G., Theodosis-Nobelos, P., and Rekka, E.A. (2022). Nipecotic Acid Derivatives as Potent Agents against Neurodegeneration: A Preliminary Study. Molecules, 27.","DOI":"10.3390\/molecules27206984"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Roychoudhury, S., Sinha, B., Choudhury, B.P., Jha, N.K., Palit, P., Kundu, S., Mandal, S.C., Kolesarova, A., Yousef, M.I., and Ruokolainen, J. (2021). Scavenging Properties of Plant-Derived Natural Biomolecule Para-Coumaric Acid in the Prevention of Oxidative Stress-Induced Diseases. Antioxidants, 10.","DOI":"10.3390\/antiox10081205"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Yu, X.D., Zhang, D., Xiao, C.L., Zhou, Y., Li, X., Wang, L., He, Z., Reilly, J., Xiao, Z.Y., and Shu, X. (2022). P-Coumaric Acid Reverses Depression-Like Behavior and Memory Deficit Via Inhibiting AGE-RAGE-Mediated Neuroinflammation. Cells, 11.","DOI":"10.3390\/cells11101594"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/j.nefroe.2020.06.017","article-title":"Antioxidant effect of p-coumaric acid on interleukin 1-\u03b2 and tumor necrosis factor-\u03b1 in rats with renal ischemic reperfusion","volume":"40","author":"Gholizadeh","year":"2020","journal-title":"Nefrologia (Engl. Ed.)"},{"key":"ref_38","first-page":"4068","article-title":"A Possible Anti-Inflammatory Effect of Proline in the Brain Cortex and Cerebellum of Rats","volume":"55","author":"Andrade","year":"2018","journal-title":"Mol. Neurobiol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1016\/j.freeradbiomed.2016.01.007","article-title":"The metabolites of glutamine prevent hydroxyl radical-induced apoptosis through inhibiting mitochondria and calcium ion involved pathways in fish erythrocytes","volume":"92","author":"Li","year":"2016","journal-title":"Free Radic. Biol. Med."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"20022","DOI":"10.1021\/acs.jmedchem.4c01987","article-title":"Proline Analogues in Drug Design: Current Trends and Future Prospects","volume":"67","author":"Kubyshkin","year":"2024","journal-title":"J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"130194","DOI":"10.1016\/j.bmcl.2025.130194","article-title":"Tyrosine and proline conjugated trolox, hydroxy-cinnnamic acid and diclofenac hybrids as strong hypolipidemic and anti-inflammatory agents","volume":"122","author":"Rekka","year":"2025","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Theodosis-Nobelos, P., Marc, G., and Rekka, E.A. (2024). Design, Synthesis and Evaluation of Antioxidant and NSAID Derivatives with Antioxidant, Anti-Inflammatory and Plasma Lipid Lowering Effects. Molecules, 29.","DOI":"10.3390\/molecules29051016"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1531","DOI":"10.1055\/s-0033-1350897","article-title":"In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors","volume":"79","author":"Adolpho","year":"2013","journal-title":"Planta Med."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3010","DOI":"10.1021\/jm900143u","article-title":"Gamma-aminobutyric acid amides of nortriptyline and fluoxetine display improved pain suppressing activity","volume":"52","author":"Rephaeli","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_45","first-page":"41","article-title":"Anticonvulsant drugs, oxidative stress and nitric oxide","volume":"54","year":"2011","journal-title":"Proc. West. Pharmacol. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1186\/1423-0127-18-75","article-title":"Pu-Erh tea and GABA attenuates oxidative stress in kainic acid-induced status epilepticus","volume":"18","author":"Hou","year":"2011","journal-title":"J. Biomed. Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1016\/j.pharep.2014.09.004","article-title":"A review on Alzheimer\u2019s disease pathophysiology and its management: An update","volume":"67","author":"Kumar","year":"2015","journal-title":"Pharmacol. Rep."},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Heo, S., Kim, S., and Kang, D. (2020). The Role of Hydrogen peroxide and peroxiredoxins in the cell cycle. Antioxidants, 9.","DOI":"10.3390\/antiox9040280"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/j.saa.2013.06.110","article-title":"Spectroscopic studies on the antioxidant activity of p-coumaric acid","volume":"115","author":"Kilic","year":"2013","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"e10467","DOI":"10.1016\/j.heliyon.2022.e10467","article-title":"Structure-antiradical activity relationships of 25 natural antioxidant phenolic compounds from different classes","volume":"8","author":"Moazzen","year":"2022","journal-title":"Heliyon"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2759","DOI":"10.1097\/MS9.0000000000001717","article-title":"Iron chelators: As therapeutic agents in diseases","volume":"86","author":"Salimi","year":"2024","journal-title":"Ann. Med. Surg."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"3460","DOI":"10.2174\/138161211798072463","article-title":"Importance of Iron Chelation in Free Radical-Induced Oxidative Stress and Human Disease","volume":"17","author":"Jomova","year":"2011","journal-title":"Curr. Pharm. Des."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1021\/acscentsci.7b00028","article-title":"On the Mechanism of Cytoprotection by Ferrostatin-1 and Liproxstatin-1 and the Role of Lipid Peroxidation in Ferroptotic Cell Death","volume":"3","author":"Zilka","year":"2017","journal-title":"ACS Cent. Sci."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3309","DOI":"10.3390\/molecules20023309","article-title":"Prevention of Protein Glycation by Natural Compounds","volume":"20","author":"Bartosz","year":"2015","journal-title":"Molecules"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"579","DOI":"10.2174\/1570180818666211210161922","article-title":"Gabapentin Antioxidant Derivatives with Anti-Inflammatory and neuroprotective potency","volume":"19","author":"Papagiouvannis","year":"2022","journal-title":"Lett. Drug Des. Discov."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1007\/s12265-025-10605-2","article-title":"Roles of Lipoxygenases in Cardiovascular Diseases","volume":"18","author":"Liu","year":"2025","journal-title":"J. Cardiovasc. Transl. Res."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3549","DOI":"10.1080\/14796694.2024.2419356","article-title":"Research progress on the role of lipoxygenase and its inhibitors in prostate cancer","volume":"20","author":"Li","year":"2024","journal-title":"Futur. Oncol."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3571","DOI":"10.1007\/s10787-024-01557-1","article-title":"Leukotriene signalling in neurodegeneration: Implications for treatment strategies","volume":"32","author":"Sharma","year":"2024","journal-title":"Inflammopharmacology"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"356","DOI":"10.1016\/j.ejps.2018.06.003","article-title":"Safer anti-inflammatory therapy through dual COX-2\/5-LOX inhibitors: A structure-based approach","volume":"121","author":"P","year":"2018","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1002\/path.1711040103","article-title":"Studies on the mediators of the acute inflammatory response induced in rats in different sites by carrageenan and turpentine","volume":"104","author":"Giroud","year":"1971","journal-title":"J. Pathol."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"225","DOI":"10.2174\/1389450124666221213114500","article-title":"A Review on Recent Development of Novel Heterocycles as Acetylcholinesterase Inhibitor for the Treatment of Alzheimer\u2019s Disease","volume":"24","author":"Patel","year":"2023","journal-title":"Curr. Drug Targets"},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Papagiouvannis, G., Theodosis-Nobelos, P., and Rekka, E.A. (2024). Trolox, ferulic, Sinapic, and Cinnamic Acid derivatives of Proline and GABA with Antioxidant and\/or Anti-Inflammatory Properties. Molecules, 29.","DOI":"10.3390\/molecules29163763"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"e10082","DOI":"10.1016\/j.heliyon.2022.e10082","article-title":"Evaluation of the anti-inflammatory and antioxidant potential of the stem bark extract and some constituents of Aidia genipiflora (DC.) dandy (rubiaceae)","volume":"8","author":"Anokwah","year":"2022","journal-title":"Heliyon"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"787","DOI":"10.2147\/DDDT.S288389","article-title":"Dopamine-Mediated Vanillin Multicomponent Derivative Synthesis via Grindstone Method: Application of Antioxidant, Anti-Tyrosinase, and Cytotoxic Activities","volume":"15","author":"Mani","year":"2021","journal-title":"Drug Des. Dev. Ther."},{"key":"ref_65","doi-asserted-by":"crossref","unstructured":"Manolov, S., Bojilov, D., Ivanov, I., Marc, G., Bataklieva, N., Oniga, S., Oniga, O., and Nedialkov, P. (2023). Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles. Processes, 11.","DOI":"10.3390\/pr11061837"},{"key":"ref_66","doi-asserted-by":"crossref","unstructured":"Marc, G., Stana, A., Oniga, S.D., P\u00eern\u0103u, A., Vlase, L., and Oniga, O. (2019). New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies. Molecules, 24.","DOI":"10.3390\/molecules24112060"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"480","DOI":"10.1016\/j.indcrop.2018.12.010","article-title":"Antioxidant properties of phenolic surrogates of lignin depolymerisation","volume":"129","author":"Cesari","year":"2019","journal-title":"Ind. Crops Prod."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1007\/s00044-016-1767-8","article-title":"Novel polyfunctional esters of ibuprofen and ketoprofen with hypolipidemic, lipoxygenase inhibitory and enhanced anti-inflammatory activity","volume":"26","author":"Tziona","year":"2017","journal-title":"Med. Chem. Res."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"3757","DOI":"10.1007\/s11030-023-10775-8","article-title":"Design, Synthesis, and Pharmacological Evaluation of Indazole Carboxamides of N-Substituted Pyrrole Derivatives as Soybean Lipoxygenase Inhibitors","volume":"28","author":"Lavrentaki","year":"2024","journal-title":"Mol. Divers."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/8\/1323\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,24]],"date-time":"2026-04-24T12:29:39Z","timestamp":1777033779000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/8\/1323"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,4,17]]},"references-count":69,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2026,4]]}},"alternative-id":["molecules31081323"],"URL":"https:\/\/doi.org\/10.3390\/molecules31081323","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,4,17]]}}}