{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T02:53:11Z","timestamp":1791859991846,"version":"4.3.4"},"reference-count":53,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2025,9,30]],"date-time":"2025-09-30T00:00:00Z","timestamp":1759190400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["www.mdpi.com"],"crossmark-restriction":true},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>Background: Inhibiting \u03b1-glucosidase and \u03b1-amylase is a well-established strategy for managing postprandial hyperglycemia in type 2 diabetes mellitus. However, the adverse effects of current \u03b1-glucosidase inhibitors (\u03b1-GIs) underscore the need for safer alternatives. Methods: This study introduces an efficient, metal-free, and environmentally friendly protocol for the selective, high-yield synthesis of 1,2-disubstituted benzimidazoles. The reaction between o-phenylenediamine and various aromatic aldehydes proceeds smoothly in water at room temperature, using cost-effective and eco-friendly catalysts such as acetylsalicylic acid (ASA) or salicylic acid (SA). The methodology exhibits broad versatility, enabled by the use of different o-phenylenediamines and a wide range of aromatic and heteroaromatic aldehydes. Results: Selected compounds were assessed for their inhibitory activity against \u03b1-glucosidase and \u03b1-amylase. While all exhibited low \u03b1-amylase inhibition, several showed significant \u03b1-glucosidase inhibition, with compounds 8s (IC50 = 0.39 \u00b1 0.04 \u03bcM), 8k (IC50 = 7.4 \u00b1 1.6 \u03bcM) and 8r (IC50 = 13.8 \u00b1 2.7 \u03bcM) emerging as the most promising candidates. Notably, none of these compounds affected Caco-2 cell viability at concentrations up to 30 \u03bcM. Additionally, compounds 8r and 8s exhibited antioxidant properties, which may be relevant in counteracting the excessive production of free radicals associated with diabetes. Preliminary molecular docking and 500 ns molecular dynamics (MD) simulations were carried out on compounds 3k, 8i, 8k, and 8p\u20138s to support and interpret the experimental biological findings qualitatively.<\/jats:p>","DOI":"10.3390\/ph18101469","type":"journal-article","created":{"date-parts":[[2025,9,30]],"date-time":"2025-09-30T08:21:51Z","timestamp":1759220511000},"page":"1469","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Sustainable Synthesis of 1,2-Disubstituted Benzimidazoles as Promising \u03b1-Glucosidase Inhibitors: In Vitro and In Silico Evaluation"],"prefix":"10.3390","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0081-5704","authenticated-orcid":false,"given":"Graziella","family":"Tocco","sequence":"first","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7227-513X","authenticated-orcid":false,"given":"Antonio","family":"Laus","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8091-7908","authenticated-orcid":false,"given":"Cristina","family":"Manis","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2448-3767","authenticated-orcid":false,"given":"Pierluigi","family":"Caboni","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3009-4226","authenticated-orcid":false,"given":"Antonella","family":"Fais","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4154-9740","authenticated-orcid":false,"given":"Benedetta","family":"Era","sequence":"additional","affiliation":[{"name":"Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria di Monserrato, 09042 Monserrato, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,9,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"365","DOI":"10.2174\/1389557521666210331163810","article-title":"Recent advancements on benzimidazole: A versatile scaffold in medicinal chemistry","volume":"22","author":"Alzhrani","year":"2022","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"111850","DOI":"10.1016\/j.ejmech.2019.111850","article-title":"Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria","volume":"186","author":"Dokla","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"e2000090","DOI":"10.1002\/ardp.202000090","article-title":"Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles","volume":"353","author":"Deswal","year":"2020","journal-title":"Arch. Pharm."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"478","DOI":"10.1016\/j.apsb.2022.09.010","article-title":"Benzimidazole and its derivatives as cancer therapeutics: The potential role from traditional to precision medicine","volume":"13","author":"Lee","year":"2023","journal-title":"Acta Pharm. Sin. B."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"28733","DOI":"10.1021\/acsomega.3c03530","article-title":"Exploration of Remarkably Potential Multitarget-Directed N-Alkylated-2-(substituted phenyl)-1H-benzimidazole Derivatives as Antiproliferative, Antifungal, and Antibacterial Agents","volume":"8","author":"Phan","year":"2023","journal-title":"ACS Omega"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Veerasamy, R., Roy, A., Karunakaran, R., and Rajak, H. (2021). Structure\u2013Activity Relationship Analysis of Benzimidazoles as Emerging Anti-Inflammatory Agents: An Overview. Pharmaceuticals, 14.","DOI":"10.3390\/ph14070663"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"7306","DOI":"10.1016\/j.bmcl.2011.10.034","article-title":"Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents","volume":"21","author":"Bandyopadhyay","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"506","DOI":"10.1016\/j.ejmech.2014.02.046","article-title":"Identification of human presequence protease (hPreP) agonists for the treatment of Alzheimer\u2019s disease","volume":"76","author":"Vangavaragu","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"\u00c7akir, B., Da\u011fliyan, O., Da\u011fyildiz, E., Bari\u015f, \u0130., Kavakli, I.H., Kizilel, S., and T\u00fcrkay, M. (2012). Structure Based Discovery of Small Molecules to Regulate the Activity of Human Insulin Degrading Enzyme. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0031787"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5858","DOI":"10.1016\/j.arabjc.2011.09.015","article-title":"Synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using chlorosulfonic acid at room temperature","volume":"9","author":"Shitole","year":"2016","journal-title":"Arab. J. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1771","DOI":"10.1016\/j.tetlet.2014.01.125","article-title":"Eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using alumina-sulfuric acid as a heterogeneous reusable catalyst","volume":"55","author":"Pramanik","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1080\/00397911.2010.524337","article-title":"Rare-Earth Metal Chlorides as Efficient Catalysts for the Simple and Green Synthesis of 1,2-Disubstituted Benzimidazoles and 2-Substituted Benzothiazoles Under Ultrasound Irradiation","volume":"42","author":"Zhang","year":"2012","journal-title":"Synth. Commun."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1016\/j.cclet.2015.04.012","article-title":"Facile one-pot clean synthesis of benzimidazole motifs: Exploration on bismuth nitrate accelerated subtle catalysis","volume":"26","author":"Mahire","year":"2015","journal-title":"Chin. Chem. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1974","DOI":"10.1016\/j.tetlet.2012.02.021","article-title":"Nano indium oxide: An efficient catalyst for the synthesis of 1, 2-disubstituted benzimidazoles in aqueous media","volume":"53","author":"Santra","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.molcata.2011.03.027","article-title":"Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles","volume":"341","author":"Bandyopadhyay","year":"2011","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"9416","DOI":"10.1039\/c3ra47366j","article-title":"Chitosan-supported Fe3O4 nanoparticles: A magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines","volume":"4","author":"Maleki","year":"2014","journal-title":"RSC Adv."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"39496","DOI":"10.1039\/C8RA07377E","article-title":"A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles","volume":"8","author":"Maphupha","year":"2018","journal-title":"RSC Adv."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1002\/jhet.5570430338","article-title":"The convenient synthesis of benzimidazole derivatives catalyzed by I2 in aqueous media","volume":"43","author":"Sun","year":"2006","journal-title":"J. Heterocycl. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1633","DOI":"10.1039\/b914286j","article-title":"Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines","volume":"11","author":"Wan","year":"2009","journal-title":"Green Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2954","DOI":"10.1002\/ajoc.202100477","article-title":"A direct metal-free synthetic approach for the efficient production of privileged benzimidazoles in water medium under aerobic condition","volume":"10","author":"Deb","year":"2021","journal-title":"Asian J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1237","DOI":"10.1039\/c000047g","article-title":"Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles","volume":"12","author":"Bahrami","year":"2010","journal-title":"Green Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1007\/s11030-015-9572-8","article-title":"Highly efficient water-mediated approach to access benzazoles: Metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles","volume":"19","author":"Bala","year":"2015","journal-title":"Mol. Divers."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1039\/b006424f","article-title":"Clean and efficient condensation reactions of aldehydes and amines in a water suspension medium","volume":"2","author":"Tanaka","year":"2000","journal-title":"Green Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"28","DOI":"10.2174\/2213337206666190214161332","article-title":"Green Synthesis of 3-Substituted-4-arylmethylideneisoxazol-5(4H)-one Derivatives Catalyzed by Salicylic Acid","volume":"6","author":"Mosallanezhad","year":"2019","journal-title":"Current Organocatal."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"217","DOI":"10.2174\/2211544707666180924125826","article-title":"Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Using Carboxylic Acids as Catalyst","volume":"7","author":"Mir","year":"2018","journal-title":"Current Catal."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"136","DOI":"10.23939\/chcht13.02.136","article-title":"Salicylic acid as a bio-based, natural and versatile catalyst for green, solvent-free and one-pot Biginelli synthesis of 3, 4-dihydropyrimidin-2-(1H)-one\/thione derivatives","volume":"13","author":"Mohamadpour","year":"2019","journal-title":"Chem. Chem. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1117","DOI":"10.1002\/jhet.4242","article-title":"Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives","volume":"58","author":"Roozifar","year":"2021","journal-title":"J. Heterocycl. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1007\/s12039-021-01891-9","article-title":"Crystalline salicylic acid as an efficient catalyst for ultrafast Paal\u2013Knorr pyrrole synthesis under microwave induction","volume":"133","author":"Aghapoor","year":"2021","journal-title":"J. Chem. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1080\/00397911.2013.838791","article-title":"Solvent-Free Synthesis of dihydropyridines and acridinediones via a salicylic acid\u2013catalyzed Hantzsch multicomponent reaction","volume":"44","author":"Khodja","year":"2014","journal-title":"Synth. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"154045","DOI":"10.1016\/j.tetlet.2022.154045","article-title":"Mukaiyama reagent: An efficient reaction mediator for rapid synthesis of 1,2-disubstituted-1H-benzo[d]imidazoles","volume":"104","author":"Tocco","year":"2022","journal-title":"Tetrahedron Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1953","DOI":"10.1080\/14756366.2020.1835884","article-title":"Scaffold hopping and optimisation of 3\u2019,4\u2019-dihydroxyphenyl- containing thienopyrimidinones: Synthesis of quinazolinone derivatives as novel allosteric inhibitors of HIV-1 reverse transcriptase-associated ribonuclease H","volume":"35","author":"Tocco","year":"2020","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"428","DOI":"10.1016\/j.ijbiomac.2020.12.117","article-title":"A new biological prospective for the 2-phenylbenzofurans as inhibitors of \u03b1-glucosidase and of the islet amyloid polypeptide formation","volume":"169","author":"Delogu","year":"2021","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1016\/j.carbpol.2010.01.002","article-title":"Digestion of starch: In vivo and in vitro kinetic models used to characterise oligosaccharide or glucose release","volume":"80","author":"Dona","year":"2010","journal-title":"Carbohydr. Polym."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"35781","DOI":"10.1039\/D3RA07156A","article-title":"Efficient synthesis of 1,2-disubstituted benzimidazoles catalyzed by phosphoric acid as a homogeneous catalyst under mild conditions and investigating their anti-diabetes properties through molecular docking studies and calculations","volume":"13","author":"Bistgani","year":"2023","journal-title":"RSC Adv."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1016\/j.jfda.2016.03.003","article-title":"Influence of gallic acid on \u03b1-amylase and \u03b1-glucosidase inhibitory properties of acarbose","volume":"24","author":"Oboh","year":"2016","journal-title":"Food Drug. Anal."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1002\/jbt.10058","article-title":"Diabetes, oxidative stress, and antioxidants: A review","volume":"17","author":"Maritim","year":"2003","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/0006-2952(93)90124-F","article-title":"Impaired antioxidant status in diabetic rat liver. Effect of vanadate","volume":"45","author":"Saxena","year":"1993","journal-title":"Biochem. Pharmacol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4105","DOI":"10.1002\/ejoc.201900732","article-title":"Intramolecular C(sp3)\u2013H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH","volume":"25","author":"Bose","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"33512","DOI":"10.1039\/D4RA06436D","article-title":"Grindstone chemistry: Protic ionic liquid-substrate tuned green synthesis of 1,2-disubstituted and 2-substituted benzimidazoles with outstanding selectivity","volume":"14","author":"Das","year":"2024","journal-title":"RSC Adv."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4551","DOI":"10.1016\/j.bmc.2018.07.049","article-title":"A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity","volume":"26","author":"Chaturvedi","year":"2018","journal-title":"Bioorg. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2724","DOI":"10.1007\/s10562-017-2166-6","article-title":"Nano Copper(0)-Stabilized on Alumina: Efficient and Recyclable Heterogeneous Catalyst for Chemoselective Synthesis of 1,2-Disubstituted Benzimidazoles and Quinoxalines in Aqueous Medium","volume":"147","author":"Pogula","year":"2017","journal-title":"Catal. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1002\/cplu.201900349","article-title":"A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation-Cyclization and Oxidative Coupling Reactions","volume":"85","author":"Sang","year":"2020","journal-title":"ChemPlusChem"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3821","DOI":"10.1021\/jo5000797","article-title":"Molecular Iodine Promoted Divergent Synthesis of Benzimidazoles, Benzothiazoles, and 2-Benzyl-3-phenyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazines","volume":"79","author":"Naresh","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4013","DOI":"10.1039\/C8NJ05504A","article-title":"Bimetallic Cu\u2013Mn B spinel oxide catalyzed oxidative synthesis of 1,2-disubstituted benzimidazoles from benzyl bromides","volume":"43","author":"Sharma","year":"2019","journal-title":"New J. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"698","DOI":"10.1016\/j.ejmech.2014.07.071","article-title":"Discovery of N-(2-phenyl-1H-benzo[d] imidazol-5-yl) quinolin-4-amine derivatives as novel VEGFR-2 kinase inhibitors","volume":"84","author":"Shi","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"5295","DOI":"10.1021\/jo2005632","article-title":"Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C\u2013H Functionalization\/C\u2013N\/C\u2013O Bond Formation","volume":"76","author":"Guru","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1080\/14756366.2021.1874945","article-title":"Washingtonia filifera seed extracts inhibit the islet amyloid polypeptide fibrils formations and \u03b1-amylase and \u03b1-glucosidase activity","volume":"36","author":"Floris","year":"2021","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Floris, S., Pintus, F., Fais, A., Era, B., Raho, N., Siguri, C., Orr\u00f9, G., Fais, S., Tuberoso, C.I.G., and Olla, S. (2024). Biological Potential of Asphodelus microcarpus Extracts: \u03b1-Glucosidase and Antibiofilm Activities In Vitro. Molecules, 29.","DOI":"10.3390\/molecules29215063"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1016\/j.foodchem.2009.03.108","article-title":"Biological Evaluations of Novel Vitamin C Esters as Mushroom Tyrosinase Inhibitors and Antioxidants","volume":"117","author":"Yi","year":"2009","journal-title":"Food Chem."},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med., 26.","DOI":"10.1016\/S0891-5849(98)00315-3"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"W296","DOI":"10.1093\/nar\/gky427","article-title":"SWISS-MODEL: Homology modelling of protein structures and complexes","volume":"46(W1)","author":"Waterhouse","year":"2018","journal-title":"Nucleic Acids Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4066","DOI":"10.1021\/acs.jmedchem.5b00104","article-title":"pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph-Based Signatures","volume":"58","author":"Pires","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"107952","DOI":"10.1016\/j.bioorg.2024.107952","article-title":"Discovery and synthesis of novel phenoxyacetate ester Schiff base \u03b1-glucosidase inhibitors","volume":"154","author":"Fan","year":"2025","journal-title":"Bioorg. Chem."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/18\/10\/1469\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,9,30]],"date-time":"2025-09-30T08:29:10Z","timestamp":1759220950000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/18\/10\/1469"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9,30]]},"references-count":53,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2025,10]]}},"alternative-id":["ph18101469"],"URL":"https:\/\/doi.org\/10.3390\/ph18101469","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,9,30]]}}}