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

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 ade...

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Autores principales: Queiroz, Thayane M., Orozco, Erika V.M., Silva, Valdenizia R., Santos, Luciano S., Soares, Milena B.P., Bezerra, Daniel P., Porto, André L.M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6734327/
https://www.ncbi.nlm.nih.gov/pubmed/31517128
http://dx.doi.org/10.1016/j.heliyon.2019.e02408
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author Queiroz, Thayane M.
Orozco, Erika V.M.
Silva, Valdenizia R.
Santos, Luciano S.
Soares, Milena B.P.
Bezerra, Daniel P.
Porto, André L.M.
author_facet Queiroz, Thayane M.
Orozco, Erika V.M.
Silva, Valdenizia R.
Santos, Luciano S.
Soares, Milena B.P.
Bezerra, Daniel P.
Porto, André L.M.
author_sort Queiroz, Thayane M.
collection PubMed
description 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 IC(50) 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).
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spelling pubmed-67343272019-09-12 Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity Queiroz, Thayane M. Orozco, Erika V.M. Silva, Valdenizia R. Santos, Luciano S. Soares, Milena B.P. Bezerra, Daniel P. Porto, André L.M. Heliyon Article 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 IC(50) 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). Elsevier 2019-09-06 /pmc/articles/PMC6734327/ /pubmed/31517128 http://dx.doi.org/10.1016/j.heliyon.2019.e02408 Text en © 2019 The Authors. Published by Elsevier Ltd. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Queiroz, Thayane M.
Orozco, Erika V.M.
Silva, Valdenizia R.
Santos, Luciano S.
Soares, Milena B.P.
Bezerra, Daniel P.
Porto, André L.M.
Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title_full Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title_fullStr Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title_full_unstemmed Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title_short Semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
title_sort semi-synthesis of β-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6734327/
https://www.ncbi.nlm.nih.gov/pubmed/31517128
http://dx.doi.org/10.1016/j.heliyon.2019.e02408
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