{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T08:30:38Z","timestamp":1786609838819,"version":"build-2736575974"},"reference-count":52,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T00:00:00Z","timestamp":1786579200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002322","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico (CNPq), Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"https:\/\/ror.org\/00x0ma614","id-type":"ROR","asserted-by":"publisher"}]},{"name":"Funda\u00e7\u00e3o de Apoio \u00e0 Pesquisa Cient\u00edfica e Tecnol\u00f3gica do Estado de Santa Catarina"},{"id":[{"id":"https:\/\/ror.org\/04c807f09","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The treatment of gastric ulcers based on antisecretory drugs is often associated with side effects and high recurrence rates, reinforcing the need for new therapeutic alternatives. Medicinal chemistry guided by natural prototypes represents a productive strategy in this context. The antiulcer potential of 2-phenylquinoline (2-PQ), an alkaloid from Conchocarpus longifolius (A.St.-Hil.) Kallunki &amp; Pirani (syn. Galipea longiflora Krause), has been previously reported by our research group. In the present work, four 2-PQ derivatives were synthesized\u20142,4-diphenylquinoline (1), 2-(4-methoxyphenyl) quinoline (2), 2-phenylquinolin-4-ol (3), and 4-methoxy-2-phenylquinoline (4)\u2014and evaluated for gastroprotective activity in the HCl\/ethanol-induced gastric ulcer model in mice. The quinoline derivatives were prepared mainly by trifluoroacetic acid-catalyzed condensations of aminated benzaldehyde or benzophenone precursors with the corresponding ketones under reflux at 100 \u00b0C, affording yields of 68\u201394%. Compound 3 was synthesized via a two-step sequence involving the acylation of 2-aminobenzophenone followed by base-induced cyclization, providing an 85% yield. Compound 4 was obtained by O-methylation of compound 3 using iodomethane (MeI) and potassium carbonate (K2CO3) in dimethylformamide (DMF), affording a 95% yield. So, this study provides the first comparative analysis linking structural modifications to gastroprotective activity in synthetic quinoline derivatives inspired by 2-phenylquinoline, a natural alkaloid previously shown to exert gastroprotective effects. Carbenoxolone (200 mg\/kg, p.o., positive control) inhibited gastric lesion formation by 94.1%. The synthetic quinoline derivatives also showed significant gastroprotective activity after oral administration (30 mg\/kg), reducing ulcer area by 72.4% (compound 1), 76.1% (compound 2), 49.1% (compound 3), and 66.1% (compound 4). Compounds 2, 3, and 4 further retained efficacy following intraperitoneal administration (3 mg\/kg), whereas compound 1 was inactivated by this route. Overall, compound 4 exhibited the greatest efficacy, significantly reducing the gastric lesion area, decreasing lipid hydroperoxide (LOOH) and tumor necrosis factor-alpha (TNF-\u03b1) levels, and increasing glutathione (GSH) content in ulcerated gastric tissue. These findings suggest that its gastroprotective effects are mediated by antioxidant and anti-inflammatory mechanisms, identifying compound 4 as the most promising candidate for the prevention and treatment of peptic ulcers. Its promising pharmacological profile warrants further investigation to elucidate its molecular mechanisms of action, assess its safety and efficacy in additional preclinical studies, and explore its potential for future therapeutic development.<\/jats:p>","DOI":"10.3390\/molecules31162815","type":"journal-article","created":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T08:06:16Z","timestamp":1786608376000},"page":"2815","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Bioinspired Quinoline-2 Derivatives Based on the Natural Alkaloid 2-Phenylquinoline from Conchocarpus longifolius (A.St.-Hil.) Kallunki &amp; Pirani: Pharmacological Evaluation of Their Gastroprotective Potential"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9294-7290","authenticated-orcid":false,"given":"S\u00e9rgio","family":"Fallone de Andrade","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, 1649-003 Lisbon, Portugal"},{"name":"Department of Pharmacy, Pharmacology and Health Technologies, Faculty of Pharmacy, Lisbon University, 1649-003 Lisbon, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-8134-2285","authenticated-orcid":false,"given":"Eduardo","family":"Breviglieri","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, N\u00facleo de Investiga\u00e7\u00f5es Qu\u00edmico-Farmac\u00eauticas (NIQFAR), Universidade do Vale do Itaja\u00ed\u2014UNIVALI, Itaja\u00ed 88302-901, SC, Brazil"},{"name":"Faculdade de Medicina Est\u00e1cio de Jaragu\u00e1 do Sul, Jaragu\u00e1 do Sul 89265-100, SC, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1179-9770","authenticated-orcid":false,"given":"Ivan","family":"Limachi","sequence":"additional","affiliation":[{"name":"Center for Analysis and Synthesis (CAS), Lund University, 221 00 Lund, Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5329-7301","authenticated-orcid":false,"given":"Luisa Mota","family":"da Silva","sequence":"additional","affiliation":[{"name":"Department of Pharmacology, Laboratory of Pharmacology Applied to the Gastrointestinal Tract and Its Interactions, Universidade Federal de Santa Catarina, Florianopolis 88040-900, SC, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3793-6166","authenticated-orcid":false,"given":"Thaise","family":"Boeing","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, N\u00facleo de Investiga\u00e7\u00f5es Qu\u00edmico-Farmac\u00eauticas (NIQFAR), Universidade do Vale do Itaja\u00ed\u2014UNIVALI, Itaja\u00ed 88302-901, SC, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8435-7124","authenticated-orcid":false,"given":"Lincon Bordignon","family":"Somensi","sequence":"additional","affiliation":[{"name":"Graduate Program in Development and Society, Universidade Alto Vale do Rio do Peixe (UNIARP), Rua Victor Baptista Adami, 800, Ca\u00e7ador 89500-199, SC, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4470-6569","authenticated-orcid":false,"given":"Olov","family":"Sterner","sequence":"additional","affiliation":[{"name":"Center for Analysis and Synthesis (CAS), Lund University, 221 00 Lund, Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7176-7810","authenticated-orcid":false,"given":"Alberto","family":"Gimenez","sequence":"additional","affiliation":[{"name":"Instituto de Investigaciones F\u00e1rmaco Bioqu\u00edmicas (IIFB), Universidad Mayor de San Andr\u00e9s, La Paz, Bolivia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8947-2965","authenticated-orcid":false,"given":"Valdir","family":"Cechinel Filho","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, N\u00facleo de Investiga\u00e7\u00f5es Qu\u00edmico-Farmac\u00eauticas (NIQFAR), Universidade do Vale do Itaja\u00ed\u2014UNIVALI, Itaja\u00ed 88302-901, SC, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,8,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"116436","DOI":"10.1016\/j.ejmech.2024.116436","article-title":"From Lab to Nature: Recent Advancements in the Journey of Gastroprotective Agents from Medicinal Chemistry to Phytotherapy","volume":"272","author":"Yadav","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"01","DOI":"10.58489\/2836-6204\/004","article-title":"Peptic Ulcer Disease and Its Implications","volume":"1","year":"2023","journal-title":"RGMH"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/j.medcli.2023.05.008","article-title":"Peptic Ulcer","volume":"161","author":"Laucirica","year":"2023","journal-title":"Med. Clin."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Hao, W., Zheng, C., Wang, Z., and Ma, H. (2025). Global Burden and Risk Factors of Peptic Ulcer Disease between 1990 and 2021: An Analysis from the Global Burden of Disease Study 2021. PLoS ONE, 20.","DOI":"10.1371\/journal.pone.0325821"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"285","DOI":"10.5946\/ce.2015.48.4.285","article-title":"Diagnostic and Treatment Approaches for Refractory Peptic Ulcers","volume":"48","author":"Kim","year":"2015","journal-title":"Clin. Endosc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"100728","DOI":"10.1016\/j.cpsurg.2019.100728","article-title":"Surgical Management of Peptic Ulcer Disease","volume":"57","author":"Wang","year":"2020","journal-title":"Curr. Probl. Surg."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1055\/a-2256-6592","article-title":"Recent Advances in Molecular Pathways and Therapeutic Implications for Peptic Ulcer Management: A Comprehensive Review","volume":"56","author":"Joshi","year":"2024","journal-title":"Horm. Metab. Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"9099","DOI":"10.3390\/molecules20059099","article-title":"Gaseous Mediators Nitric Oxide and Hydrogen Sulfide in the Mechanism of Gastrointestinal Integrity, Protection and Ulcer Healing","volume":"20","author":"Magierowski","year":"2015","journal-title":"Molecules"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Tarnawski, A.S., and Ahluwalia, A. (2021). The Critical Role of Growth Factors in Gastric Ulcer Healing: The Cellular and Molecular Mechanisms and Potential Clinical Implications. Cells, 10.","DOI":"10.3390\/cells10081964"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1016\/S0140-6736(16)32404-7","article-title":"Peptic Ulcer Disease","volume":"390","author":"Lanas","year":"2017","journal-title":"Lancet"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1016\/j.joim.2025.12.002","article-title":"Gastroprotective Activity of Talinum paniculatum (Jacq.) Gaertn. in Mice: An Ethnopharmacological Validation","volume":"24","author":"Zanovello","year":"2026","journal-title":"J. Integr. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"e001719","DOI":"10.1136\/bmjgast-2024-001719","article-title":"Proton Pump Inhibitors and the Risk of Gastric Cancer: A Systematic Review, Evidence Synthesis and Life Course Epidemiology Perspective","volume":"12","author":"Brusselaers","year":"2025","journal-title":"BMJ Open Gastroenterol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1038\/s41416-020-0860-4","article-title":"Use of Proton Pump Inhibitors and Histamine-2 Receptor Antagonists and Risk of Gastric Cancer in Two Population-Based Studies","volume":"123","author":"Liu","year":"2020","journal-title":"Br. J. Cancer"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.phymed.2016.12.016","article-title":"Gastroprotective and Anti-Secretory Mechanisms of 2-Phenylquinoline, an Alkaloid Isolated from Galipea longiflora","volume":"25","author":"Breviglieri","year":"2017","journal-title":"Phytomedicine"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"17020","DOI":"10.3748\/wjg.v20.i45.17020","article-title":"Efficacy and Safety of Herbal Medicines in Treating Gastric Ulcer: A Review","volume":"20","author":"Bi","year":"2014","journal-title":"World J. Gastroenterol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1111\/sji.12010","article-title":"Quinolinic Alkaloids from Galipea longiflora Krause Suppress Production of Proinflammatory Cytokines in Vitro and Control Inflammation in Vivo upon Leishmania Infection in Mice","volume":"77","author":"Quispe","year":"2013","journal-title":"Scand. J. Immunol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1914","DOI":"10.1248\/cpb.42.1914","article-title":"Synthesis of an Antileishmanial Alkaloid Isolated from Galipea longiflora and of Related Compounds","volume":"42","author":"Munos","year":"1994","journal-title":"Chem. Pharm. Bull."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Elebiju, O.F., Ajani, O.O., Oduselu, G.O., Ogunnupebi, T.A., and Adebiyi, E. (2022). Recent Advances in Functionalized Quinoline Scaffolds and Hybrids-Exceptional Pharmacophore in Therapeutic Medicine. Front. Chem., 10.","DOI":"10.3389\/fchem.2022.1074331"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4386","DOI":"10.2174\/09298673113209990170","article-title":"Medicinal Chemistry of Quinolines as Emerging Anti-Inflammatory Agents: An Overview","volume":"20","author":"Mukherjee","year":"2013","journal-title":"Curr. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"248","DOI":"10.2174\/1570179417666201216162055","article-title":"Recent Developments of Quinoline Derivatives and Their Potential Biological Activities","volume":"18","author":"Dib","year":"2021","journal-title":"Curr. Org. Synth."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"11949","DOI":"10.1021\/acs.jmedchem.2c00390","article-title":"Discovery of Novel Imidazo[4,5-c]Quinoline Derivatives to Treat Inflammatory Bowel Disease (IBD) by Inhibiting Multiple Proinflammatory Signaling Pathways and Restoring Intestinal Homeostasis","volume":"65","author":"Liang","year":"2022","journal-title":"J. Med. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"133665","DOI":"10.1016\/j.molstruc.2022.133665","article-title":"Structure Modifications of 2-Phenylquinoline by Aspergillus Genera Produce Novel Derivatives with Potent Leishmanicidal and Anti-Inflammatory Properties","volume":"1268","author":"Mischiatti","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"25","DOI":"10.47352\/bioactivities.2963-654X.278","article-title":"Acute Toxicity of Quinoline Derivatives as Antibacterial Drug Candidates: In Silico and In Vivo Studies","volume":"3","author":"Hodyna","year":"2025","journal-title":"Bioactivities"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jsps.2012.03.002","article-title":"Quinoline: A Versatile Heterocyclic","volume":"21","author":"Marella","year":"2013","journal-title":"Saudi Pharm. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3646","DOI":"10.1039\/D4RA08362H","article-title":"Quinoline Analogs: Multifaceted Heterocyclic Compounds with Varied Synthetic Strategies and Potent Antitubercular Properties","volume":"15","author":"Pakhariya","year":"2025","journal-title":"RSC Adv."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"20784","DOI":"10.1039\/D0RA03763J","article-title":"Recent Advances in the Synthesis of Biologically and Pharmaceutically Active Quinoline and Its Analogues: A Review","volume":"10","author":"Weyesa","year":"2020","journal-title":"RSC Adv."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1080\/14756366.2016.1190714","article-title":"Synthesis and Evaluation of Antibacterial and Antioxidant Activity of Novel 2-Phenyl-Quinoline Analogs Derivatized at Position 4 with Aromatically Substituted 4H-1,2,4-Triazoles","volume":"31","author":"Verbanac","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"228","DOI":"10.1016\/S0016-5085(85)80176-1","article-title":"Early Vascular Injury and Increased Vascular Permeability in Gastric Mucosal Injury Caused by Ethanol in the Rat","volume":"88","author":"Szabo","year":"1985","journal-title":"Gastroenterology"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Adlia, A., Aslan, C.C., Safitri, L., and Adnyana, I.K. (2025). Turmeric-Black Pepper-Honey Nanoemulsion Formulation and Antiulcerogenic Effect Evaluation against Ethanol-Induced Gastric Ulcers in Rats. PLoS ONE, 20.","DOI":"10.1371\/journal.pone.0317899"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1025","DOI":"10.1177\/1535370216686221","article-title":"Autophagy Protects Gastric Mucosal Epithelial Cells from Ethanol-Induced Oxidative Damage via mTOR Signaling Pathway","volume":"242","author":"Chang","year":"2017","journal-title":"Exp. Biol. Med."},{"key":"ref_31","first-page":"613","article-title":"Lipid Peroxidation, Reactive Oxygen Species and Antioxidative Factors in the Pathogenesis of Gastric Mucosal Lesions and Mechanism of Protection against Oxidative Stress\u2014Induced Gastric Injury","volume":"65","author":"Kwiecien","year":"2014","journal-title":"J. Physiol. Pharmacol."},{"key":"ref_32","first-page":"39","article-title":"Effects of Reactive Oxygen Species Action on Gastric Mucosa in Various Models of Mucosal Injury","volume":"53","author":"Brzozowski","year":"2002","journal-title":"J. Physiol. Pharmacol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1053\/j.gastro.2008.05.030","article-title":"Gastric Mucosal Defense and Cytoprotection: Bench to Bedside","volume":"135","author":"Laine","year":"2008","journal-title":"Gastroenterology"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"360438","DOI":"10.1155\/2014\/360438","article-title":"Lipid Peroxidation: Production, Metabolism, and Signaling Mechanisms of Malondialdehyde and 4-Hydroxy-2-Nonenal","volume":"2014","author":"Ayala","year":"2014","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"9","DOI":"10.3164\/jcbn.12-112","article-title":"Lipid Peroxidation Biomarkers for Evaluating Oxidative Stress and Assessing Antioxidant Capacity in Vivo","volume":"52","author":"Yoshida","year":"2013","journal-title":"J. Clin. Biochem. Nutr."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1007\/PL00010046","article-title":"The Role of Lipid Peroxidation on Gastric Mucosal Lesions Induced by Water-Immersion-Restraint Stress in Rats","volume":"30","author":"Shian","year":"2000","journal-title":"Surg. Today"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1016\/j.cyto.2009.03.010","article-title":"Tumor Necrosis Factor (TNF)-Alpha-Induced IL-8 Expression in Gastric Epithelial Cells: Role of Reactive Oxygen Species and AP Endonuclease-1\/Redox Factor (Ref)-1","volume":"46","author":"Bhattacharyya","year":"2009","journal-title":"Cytokine"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.cyto.2018.01.003","article-title":"Association of TNF-\u03b1 but Not IL-1\u03b2 Levels with the Presence of Helicobacter Pylori Infection Increased the Risk of Peptic Ulcer Development","volume":"110","author":"Tourani","year":"2018","journal-title":"Cytokine"},{"key":"ref_39","first-page":"163","article-title":"Changes in Glutathione in Gastric Mucosa of Gastric Ulcer Patients","volume":"88","author":"Hirokawa","year":"1995","journal-title":"Res. Commun. Mol. Pathol. Pharmacol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1136\/gut.50.2.235","article-title":"Influence of Clinical Factors, Diet, and Drugs on the Human Upper Gastrointestinal Glutathione System","volume":"50","author":"Hoensch","year":"2002","journal-title":"Gut"},{"key":"ref_41","first-page":"G296","article-title":"Role of Glutathione in Gastric Mucosal Cytoprotection","volume":"247","author":"Robert","year":"1984","journal-title":"Am. J. Physiol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"18594","DOI":"10.1039\/D2RA02896D","article-title":"Recent Advances in Chemistry and Therapeutic Potential of Functionalized Quinoline Motifs\u2014A Review","volume":"12","author":"Ajani","year":"2022","journal-title":"RSC Adv."},{"key":"ref_43","first-page":"365","article-title":"Recent Studies of Antioxidant Quinoline Derivatives","volume":"13","author":"Tekiner","year":"2013","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2385","DOI":"10.1111\/j.1572-0241.1998.00692.x","article-title":"Physiological Role of Cholecystokinin in Gastroprotection in Humans","volume":"93","author":"Konturek","year":"1998","journal-title":"Am. J. Gastroenterol."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"818","DOI":"10.1021\/mp800035h","article-title":"Computational Model for Predicting Chemical Substituent Effects on Passive Drug Permeability across Parallel Artificial Membranes","volume":"5","author":"Acharya","year":"2008","journal-title":"Mol. Pharm."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0169-409X(00)00129-0","article-title":"Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings","volume":"46","author":"Lipinski","year":"2001","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1080\/17568919.2025.2485865","article-title":"Methoxy Group: A Non-Lipophilic \u201cScout\u201d for Protein Pocket Finding","volume":"17","author":"Chiodi","year":"2025","journal-title":"Future Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"10050","DOI":"10.1002\/slct.201702200","article-title":"Aminoquinoline Schiff Bases as Non-Acidic, Non-Steroidal, Anti-Inflammatory Agents","volume":"2","author":"Bano","year":"2017","journal-title":"ChemistrySelect"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"30576","DOI":"10.1039\/D5RA00534E","article-title":"Quinoline Derivatives\u2019 Biological Interest for Anti-Malarial and Anti-Cancer Activities: An Overview","volume":"15","author":"Chavan","year":"2025","journal-title":"RSC Adv."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1254\/fpj.85.443","article-title":"Effects of gefarnate on acute gastric lesions in rats","volume":"85","author":"Hara","year":"1985","journal-title":"Folia Pharmacol. Jpn."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1007\/BF02536169","article-title":"Lipid Hydroperoxide Measurement by Oxidation of Fe2+ in the Presence of Xylenol Orange. Comparison with the TBA Assay and an Iodometric Method","volume":"26","author":"Jiang","year":"1991","journal-title":"Lipids"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"192","DOI":"10.1016\/0003-2697(68)90092-4","article-title":"Estimation of Total, Protein-Bound, and Nonprotein Sulfhydryl Groups in Tissue with Ellman\u2019s Reagent","volume":"25","author":"Sedlak","year":"1968","journal-title":"Anal. Biochem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/16\/2815\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T08:06:30Z","timestamp":1786608390000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/16\/2815"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,13]]},"references-count":52,"journal-issue":{"issue":"16","published-online":{"date-parts":[[2026,8]]}},"alternative-id":["molecules31162815"],"URL":"https:\/\/doi.org\/10.3390\/molecules31162815","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,13]]}}}