{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,11]],"date-time":"2026-05-11T23:35:40Z","timestamp":1778542540129,"version":"3.51.4"},"reference-count":49,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2021,9,22]],"date-time":"2021-09-22T00:00:00Z","timestamp":1632268800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["473085"],"award-info":[{"award-number":["473085"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["231815"],"award-info":[{"award-number":["231815"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["364335"],"award-info":[{"award-number":["364335"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Dapsone (DDS) is an antibacterial drug with well-known antioxidant properties. However, the antioxidant behavior of its derivatives has not been well explored. In the present work, the antioxidant activity of 10 dapsone derivatives 4-substituted was determined by an evaluation in two in vitro models (DPPH radical scavenging assay and ferric reducing antioxidant power). These imine derivatives 1\u201310 were obtained through condensation between DDS and the corresponding aromatic aldehydes 4-substuited. Three derivatives presented better results than DDS in the determination of DPPH (2, 9, and 10). Likewise, we have three compounds with better reducing activity than dapsone (4, 9, and 10). In order to be more insight, the redox process, a conceptual DFT analysis was carried out. Molecular descriptors such as electronic distribution, the total charge accepting\/donating capacity (I\/A), and the partial charge accepting\/donating capacity (\u03c9+\/\u03c9\u2212) were calculated to analyze the relative donor-acceptor capacity through employing a donor acceptor map (DAM). The DFT calculation allowed us to establish a relationship between GAPHOMO-LUMO and DAM with the observed antioxidant effects. According to the results, we concluded that compounds 2 and 3 have the lowest Ra values, representing a good antioxidant behavior observed experimentally in DPPH radical capturing. On the other hand, derivatives 4, 9, and 10 display the best reducing capacity activity with the highest \u03c9\u2212 and Rd values. Consequently, we propose these compounds as the best antireductants in our DDS imine derivative series.<\/jats:p>","DOI":"10.3390\/molecules26195747","type":"journal-article","created":{"date-parts":[[2021,9,22]],"date-time":"2021-09-22T22:50:48Z","timestamp":1632351048000},"page":"5747","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis, In Vitro, and In Silico Analysis of the Antioxidative Activity of Dapsone Imine Derivatives"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8219-1685","authenticated-orcid":false,"given":"Ricardo","family":"Guzm\u00e1n-\u00c1vila","sequence":"first","affiliation":[{"name":"Laboratorio 4, Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6629-5206","authenticated-orcid":false,"given":"Mayra","family":"Avelar","sequence":"additional","affiliation":[{"name":"Laboratorio de S\u00edntesis Asim\u00e9trica y Bioenerg\u00e9tica (LSAyB), Ingenier\u00eda Qu\u00edmica (UACQ), Universidad Aut\u00f3noma de Zacatecas, Campus XXI Km 6 Carr. Zac-Gdl, Zacatecas 98160, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7503-1528","authenticated-orcid":false,"given":"Edgar A.","family":"M\u00e1rquez","sequence":"additional","affiliation":[{"name":"Grupo de Investigaci\u00f3n en Qu\u00edmica y Biolog\u00eda, Departamento de Qu\u00edmica y Biolog\u00eda, Universidad del Norte, Km 5 v\u00eda Puerto Colombia 1569, Barranquilla Atl\u00e1ntico 081007, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5521-1791","authenticated-orcid":false,"given":"Julio C.","family":"Rivera-Leyva","sequence":"additional","affiliation":[{"name":"Laboratorio 4, Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6128-9504","authenticated-orcid":false,"given":"Jos\u00e9 R.","family":"Mora","sequence":"additional","affiliation":[{"name":"Grupo de Qu\u00edmica Computacional y Te\u00f3rica (QCT-USFQ), Departamento de Ingenier\u00eda Qu\u00edmica, Universidad San Francisco de Quito, Diego de Robles y V\u00eda Interoce\u00e1nica, Quito 170901, Ecuador"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4540-1011","authenticated-orcid":false,"given":"Virginia","family":"Flores-Morales","sequence":"additional","affiliation":[{"name":"Laboratorio de S\u00edntesis Asim\u00e9trica y Bioenerg\u00e9tica (LSAyB), Ingenier\u00eda Qu\u00edmica (UACQ), Universidad Aut\u00f3noma de Zacatecas, Campus XXI Km 6 Carr. Zac-Gdl, Zacatecas 98160, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jes\u00fas","family":"Rivera-Islas","sequence":"additional","affiliation":[{"name":"Laboratorio 4, Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,22]]},"reference":[{"key":"ref_1","unstructured":"World Health Organization (2020, January 29). Leprosy. Available online: https:\/\/www.who.int\/news-room\/fact-sheets\/detail\/leprosy."},{"key":"ref_2","first-page":"801","article-title":"Leprosy\u2013an overview of clinical features, diagnosis, and treatment","volume":"15","author":"Fischer","year":"2017","journal-title":"J. Dtsch. Dermatol. 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