Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity

dc.creatorQueiroz, Thayane M.
dc.creatorOrozco, Erika V. M.
dc.creatorSilva, Valdenizia Rodrigues
dc.creatorSantos, Luciano de Souza
dc.creatorSoares, Milena Botelho Pereira
dc.creatorBezerra, Daniel Pereira
dc.creatorPorto, André Luiz Meleiro
dc.date2019-10-29T12:29:01Z
dc.date2019-10-29T12:29:01Z
dc.date2019
dc.date.accessioned2023-09-27T00:12:18Z
dc.date.available2023-09-27T00:12:18Z
dc.identifierQUEIROZ, Thayane M. et al. Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity. Heliyon, v. 5, p. 1-6, 2019.
dc.identifier2405-8440
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/36727
dc.identifier10.1016/j.heliyon.2019.e02408
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8898498
dc.descriptionCoordenaç~ao de Aperfeiçoamento de Pessoal de Nível Superior (CAPES/ Proc. 1732109). Erika V.M. Orozco was supported by a fellowship provided by the Conselho Nacional de Desenvolvimento Científico e Tecnol ogico (CNPq/140824/2015-4). Andr e L.M. Porto was supported by a grant 2014/18257-0 and grant 2016/20155-7, S~ao Paulo Research Foundation (FAPESP) and Conselho Nacional de Desenvolvimento Científico e Tecnol ogico (CNPq/Proc. 302528/2017-2). This work was supported by the Coordenaç~ao de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001. The author also acknowledge the Chromatography Group (Instituto de Química de S~ao Carlos - USP), including Dr. Guilherme M. Titato for the QqToF analysis (grant 2004/09498-2, S~ao Paulo Research Foundation).
dc.descriptionIn this study, we report our contribution to the application of the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction for the synthesis of β-keto-1,2,3-triazole derivatives 3a-f from ethinylestradiol and their application in the inhibition of two human cancer cells lines: human breast adenocarcinoma (MCF-7) and human hepatocellular carcinoma (HepG2). The β-keto-1,2,3-triazole derivates 3a-f exhibited moderate cytotoxic activity for the HepG2 cells with IC50 values of 29.7 μM (3a), 16.4 μM (3b), 17.8 μM (3c), 20.4 μM (3d), 28.1 μM (3e) and 28.2 μM (3f). The semi-synthetic β-keto-1,2,3-triazoles derivatives 3a-f were all characterized by FT-IR, NMR, HRMS and [α]D.
dc.formatapplication/pdf
dc.languageeng
dc.publisherElsevier
dc.rightsopen access
dc.subjectQuímica orgânica
dc.subjectQuímica farmacêutica
dc.subjectToxicologia
dc.subjectβ-ceto-1,2,3-triazóis
dc.subjectEtinilestradiol
dc.subjectReação do clique
dc.subjectCarcinoma hepatocelular
dc.subjectAdenocarcinoma de mama
dc.subjectOrganic chemistry
dc.subjectPharmaceutical chemistry
dc.subjectToxicology
dc.subjectβ-keto-1,2,3-triazoles
dc.subjectEthinylestradiol
dc.subjectClick reaction
dc.subjectHepatocellular carcinoma
dc.subjectBreast adenocarcinoma
dc.titleSemi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
dc.typeArticle


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