{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,10]],"date-time":"2026-05-10T06:35:03Z","timestamp":1778394903504,"version":"3.51.4"},"reference-count":35,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2020,2,12]],"date-time":"2020-02-12T00:00:00Z","timestamp":1581465600000},"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":["253814"],"award-info":[{"award-number":["253814"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We prepared a series of 10 carbamates derivatives based on two common antiprotozoal drugs: metronidazole (1\u20135) and secnidazole (6\u201310). The compounds were tested in vitro against a set of two amitochondriate protozoa: Giardia duodenalis and Trichomonas vaginalis. Compounds 1\u201310 showed strong antiprotozoal activities, with potency values in the low micromolar-to-nanomolar range, being more active than their parent drugs. Metronidazole carbamate (1) was the most active of the series, with nanomolar activities against G. duodenalis (IC50 = 460 nM) and T. vaginalis (IC50 = 60 nM). The potency of compound 1 was 10 times greater than that of metronidazole against both parasites. None of compounds showed in vitro cytotoxicity against VERO cells tested at 100 \u00b5M. Molecular dynamics of compounds 1\u201310, secnidazole, and metronidazole onto the ligand binding site of pyruvate\u2013ferredoxin oxidoreductase of T. vaginalis and the modeled \u03b2-tubulin of G. duodenalis revealed putative molecular interactions with key residues in the binding site of both proteins implicated in the mode of action of the parent drugs.<\/jats:p>","DOI":"10.3390\/molecules25040793","type":"journal-article","created":{"date-parts":[[2020,2,26]],"date-time":"2020-02-26T05:44:12Z","timestamp":1582695852000},"page":"793","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Metronidazole and Secnidazole Carbamates: Synthesis, Antiprotozoal Activity, and Molecular Dynamics Studies"],"prefix":"10.3390","volume":"25","author":[{"given":"Genaro","family":"Rocha-Gardu\u00f1o","sequence":"first","affiliation":[{"name":"Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Cuernavaca, Morelos 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Norma Ang\u00e9lica","family":"Hern\u00e1ndez-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Cuernavaca, Morelos 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Blanca","family":"Col\u00edn-Lozano","sequence":"additional","affiliation":[{"name":"Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Cuernavaca, Morelos 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1860-0744","authenticated-orcid":false,"given":"Samuel","family":"Estrada-Soto","sequence":"additional","affiliation":[{"name":"Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Cuernavaca, Morelos 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7467-7538","authenticated-orcid":false,"given":"Emanuel","family":"Hern\u00e1ndez-N\u00fa\u00f1ez","sequence":"additional","affiliation":[{"name":"C\u00e1tedra CONACyT, Departamento de Recursos del Mar, Centro de Investigaci\u00f3n y de Estudios Avanzados del IPN, Unidad M\u00e9rida, Yucat\u00e1n 97310, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0054-0862","authenticated-orcid":false,"given":"Fernando Daniel","family":"Prieto-Mart\u00ednez","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, Departamento de Farmacia, Universidad Nacional Aut\u00f3noma de M\u00e9xico, M\u00e9xico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4940-1107","authenticated-orcid":false,"given":"Jos\u00e9 L.","family":"Medina-Franco","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, Departamento de Farmacia, Universidad Nacional Aut\u00f3noma de M\u00e9xico, M\u00e9xico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9905-8899","authenticated-orcid":false,"given":"Juan Bautista","family":"Chale-Dzul","sequence":"additional","affiliation":[{"name":"Laboratorio de Apoyo a la Vigilancia Epidemiol\u00f3gica, Hospital de Especialidades 1, Centro M\u00e9dico Nacional Ignacio Garc\u00eda T\u00e9llez, Instituto Mexicano del Seguro Social, M\u00e9rida 97150, Yucat\u00e1n, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9204-6062","authenticated-orcid":false,"given":"Rosa","family":"Moo-Puc","sequence":"additional","affiliation":[{"name":"Unidad de Investigaci\u00f3n M\u00e9dica Yucat\u00e1n, Unidad M\u00e9dica de Alta Especialidad, Centro M\u00e9dico Nacional Ignacio Garc\u00eda T\u00e9llez, Instituto Mexicano del Seguro Social, M\u00e9rida 97000, Yucat\u00e1n, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5344-4762","authenticated-orcid":false,"given":"Gabriel","family":"Navarrete-V\u00e1zquez","sequence":"additional","affiliation":[{"name":"Facultad de Farmacia, Universidad Aut\u00f3noma del Estado de Morelos, Cuernavaca, Morelos 62209, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,2,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/bs.apar.2019.07.003","article-title":"Giardia duodenalis: Role of secreted molecules as virulent factors in the cytotoxic effect on epithelial cells","volume":"106","year":"2019","journal-title":"Adv. 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