Author | Queiroz, Thayane M. | |
Author | Orozco, Erika V. M. | |
Author | Silva, Valdenizia Rodrigues | |
Author | Santos, Luciano de Souza | |
Author | Soares, Milena Botelho Pereira | |
Author | Bezerra, Daniel Pereira | |
Author | Porto, André Luiz Meleiro | |
Access date | 2019-10-29T12:29:01Z | |
Available date | 2019-10-29T12:29:01Z | |
Document date | 2019 | |
Citation | QUEIROZ, 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. | pt_BR |
ISSN | 2405-8440 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/36727 | |
Sponsorship | Coordenaç~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). | pt_BR |
Language | eng | pt_BR |
Publisher | Elsevier | pt_BR |
Rights | open access | pt_BR |
Subject in Portuguese | Química orgânica | pt_BR |
Subject in Portuguese | Química farmacêutica | pt_BR |
Subject in Portuguese | Toxicologia | pt_BR |
Subject in Portuguese | β-ceto-1,2,3-triazóis | pt_BR |
Subject in Portuguese | Etinilestradiol | pt_BR |
Subject in Portuguese | Reação do clique | pt_BR |
Subject in Portuguese | Carcinoma hepatocelular | pt_BR |
Subject in Portuguese | Adenocarcinoma de mama | pt_BR |
Title | Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity | pt_BR |
Type | Article | pt_BR |
DOI | 10.1016/j.heliyon.2019.e02408 | |
Abstract | In 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. | pt_BR |
Affilliation | Universidade de São Paulo. Instituto de Química de São Carlos. Laboratório de Química Orgânica e Biocatálise. São Carlos, SP, Brasil. | pt_BR |
Affilliation | Universidade de São Paulo. Instituto de Química de São Carlos. Laboratório de Química Orgânica e Biocatálise. São Carlos, SP, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisa Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Universidade de São Paulo. Instituto de Química de São Carlos. Laboratório de Química Orgânica e Biocatálise. São Carlos, SP, Brasil. | pt_BR |
Subject | Organic chemistry | pt_BR |
Subject | Pharmaceutical chemistry | pt_BR |
Subject | Toxicology | pt_BR |
Subject | β-keto-1,2,3-triazoles | pt_BR |
Subject | Ethinylestradiol | pt_BR |
Subject | Click reaction | pt_BR |
Subject | Hepatocellular carcinoma | pt_BR |
Subject | Breast adenocarcinoma | pt_BR |