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https://www.arca.fiocruz.br/handle/icict/50312
Tipo de documento
ArtigoDireito Autoral
Acesso restrito
Data de embargo
2024
Coleções
- IOC - Artigos de Periódicos [12488]
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RUTHENIUM(II)- AND PALLADIUM(II)-CATALYZED POSITION-DIVERGENT C–H OXYGENATIONS OF ARYLATED QUINONES: IDENTIFICATION OF HYDROXYLATED QUINONOID COMPOUNDS WITH POTENT TRYPANOCIDAL ACTIVITY
Autor(es)
Afiliação
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany / Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany / Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Celular. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Celular. Rio de Janeiro, RJ, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany / DZHK (German Center for Cardiovascular Research), Potsdamer Strasse 58, 10785 Berlin, Germany.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany / Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Celular. Rio de Janeiro, RJ, Brasil.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Celular. Rio de Janeiro, RJ, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077.Góttingen, Germany / DZHK (German Center for Cardiovascular Research), Potsdamer Strasse 58, 10785 Berlin, Germany.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Resumo em Inglês
A diversity-oriented synthesis of hydroxylated aryl-quinones via C–H oxygenation reactions and their evaluation
against Trypanosoma cruzi, the etiological agent of Chagas disease, was accomplished. With the use of ruthenium
(II)- or palladium(II)-based catalysts, complementary regioselectivities were observed in the hydroxylation
reactions and we have identified 9 compounds more potent than benznidazole (Bz) among these novel arylated
and hydroxylated quinones. For instance, 5-hydroxy-2-[4-(trifluoromethyl)phenyl]-1,4-naphthoquinone (4h)
with an IC50/24 h value of 22.8 μM is 4.5-fold more active than the state-of-the-art drug Bz. This article provides
the first example of the application of C–H activation for the position-selective hydroxylation of arylated
quinones and the identification of these compounds as trypanocidal drug candidates.
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