{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T04:43:18Z","timestamp":1790138598627,"version":"4.0.1"},"reference-count":51,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2025,9,8]],"date-time":"2025-09-08T00:00:00Z","timestamp":1757289600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Supercomputing Center\u2014IPICYT (Instituto Potosino de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica, A.C.) for the computational research","award":["TKII-AMVL001"],"award-info":[{"award-number":["TKII-AMVL001"]}]},{"name":"National Supercomputing Center\u2014IPICYT (Instituto Potosino de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica, A.C.) for the computational research","award":["LANCAD-UNAM-DGTIC-347"],"award-info":[{"award-number":["LANCAD-UNAM-DGTIC-347"]}]},{"name":"supercomputing resources at Miztli","award":["TKII-AMVL001"],"award-info":[{"award-number":["TKII-AMVL001"]}]},{"name":"supercomputing resources at Miztli","award":["LANCAD-UNAM-DGTIC-347"],"award-info":[{"award-number":["LANCAD-UNAM-DGTIC-347"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Type 2 diabetes mellitus (T2DM) remains a global health challenge, prompting the development of novel \u03b1-glucosidase inhibitors (AGIs) to regulate postprandial hyperglycemia. This study reports the design, synthesis, and evaluation of indole-based Schiff base derivatives (4a\u2013j) bearing a fixed methoxy group at the C5 position. This substitution was strategically introduced to enhance lipophilicity, electronic delocalization, and \u03c0-stacking within the enzyme active site. Among the series, compound 4g (3-bromophenyl) exhibited the highest inhibitory activity (IC50 = 10.89 \u00b5M), outperforming the clinical reference acarbose (IC50 = 48.95 \u00b5M). The mechanism was supported by in silico analyses, such as the Density Functional Theory (DFT), molecular electrostatic potential (MEP) mapping, and molecular dynamics simulations, and CNN-based docking revealed that 4g engages in stable hydrogen bonding and \u03c0\u2013\u03c0 interactions with key residues (Asp327, Asp542, and Phe649), suggesting a potent and selective mode of inhibition. In silico ADMET predictions indicated favorable pharmacokinetic properties. Together, these results establish C5\u2013methoxy substitution as a viable strategy to enhance \u03b1-glucosidase inhibition in indole-based scaffolds.<\/jats:p>","DOI":"10.3390\/molecules30173651","type":"journal-article","created":{"date-parts":[[2025,9,9]],"date-time":"2025-09-09T12:15:17Z","timestamp":1757420117000},"page":"3651","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Design and Evaluation of Indole-Based Schiff Bases as \u03b1-Glucosidase Inhibitors: CNN-Enhanced Docking, MD Simulations, ADMET Profiling, and SAR Analysis"],"prefix":"10.3390","volume":"30","author":[{"given":"Seema K.","family":"Bhagwat","sequence":"first","affiliation":[{"name":"Department of Chemistry, Research Centre HPT Arts, RYK Science College (Affiliated to S. P. Pune University), Nashik 422005, Maharashtra, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sachin V.","family":"Patil","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Research Centre HPT Arts, RYK Science College (Affiliated to S. P. Pune University), Nashik 422005, Maharashtra, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5674-7881","authenticated-orcid":false,"given":"Abraham","family":"Vidal-Limon","sequence":"additional","affiliation":[{"name":"Red de Estudios Moleculares Avanzados, Instituto de Ecolog\u00eda, A. C., Carretera Antigua a Coatepec 351, Xalapa 91073, Veracruz, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7354-3506","authenticated-orcid":false,"given":"J. Oscar C.","family":"Jimenez-Halla","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Divisi\u00f3n de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S\/N, Guanajuato 36050, Guanajuato, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Balasaheb K.","family":"Ghotekar","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Research Centre HPT Arts, RYK Science College (Affiliated to S. P. Pune University), Nashik 422005, Maharashtra, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vivek D.","family":"Bobade","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Research Centre HPT Arts, RYK Science College (Affiliated to S. P. Pune University), Nashik 422005, Maharashtra, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5240-5371","authenticated-orcid":false,"given":"Irving David","family":"P\u00e9rez-Landa","sequence":"additional","affiliation":[{"name":"Divisi\u00f3n de Estudios de Posgrado e Investigaci\u00f3n, Tecnol\u00f3gico Nacional de M\u00e9xico\/Instituto Tecnol\u00f3gico de Boca del R\u00edo, Carretera Veracruz-C\u00f3rdoba 12, Boca del Rio 94290, Veracruz, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6354-5222","authenticated-orcid":false,"given":"Enrique","family":"Delgado-Alvarado","sequence":"additional","affiliation":[{"name":"Micro and Nanotechnology Research Center, Universidad Veracruzana, Blvd. Av. Ruiz Cortines No. 455 Fracc. Costa Verde, Boca del Rio 94294, Veracruz, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2287-7041","authenticated-orcid":false,"given":"Fabiola","family":"Hern\u00e1ndez-Rosas","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n, Universidad An\u00e1huac Quer\u00e9taro, El Marques 76246, Queretaro, Mexico"},{"name":"Facultad de Qu\u00edmica, Universidad Aut\u00f3noma de Quer\u00e9taro, Queretaro 76010, Queretaro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0753-9538","authenticated-orcid":false,"given":"Tushar Janardan","family":"Pawar","sequence":"additional","affiliation":[{"name":"Red de Estudios Moleculares Avanzados, Instituto de Ecolog\u00eda, A. C., Carretera Antigua a Coatepec 351, Xalapa 91073, Veracruz, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,9,8]]},"reference":[{"key":"ref_1","unstructured":"World Health Organization (2024, December 31). Diabetes. Fact Sheet. Available online: https:\/\/www.who.int\/news-room\/fact-sheets\/detail\/diabetes."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/S0002-9149(01)01834-3","article-title":"Controlling Postprandial Hyperglycemia","volume":"88","author":"Ratner","year":"2001","journal-title":"Am. J. Cardiol."},{"key":"ref_3","unstructured":"International Diabetes Federation (2021). IDF Diabetes Atlas, IDF. [10th ed.]. Available online: https:\/\/diabetesatlas.org."},{"key":"ref_4","unstructured":"International Diabetes Federation (2024, December 31). Diabetes Facts and Figures. 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