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Tipo
ArtículoDerechos de autor
Acceso restringido
Fecha del embargo
2024
Objetivos de Desarrollo Sostenible
03 Saúde e Bem-EstarColecciones
- IOC - Artigos de Periódicos [12708]
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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
Afiliación
Institut für Organische und Biomolekulare Chemie, Georg-August-Universit¨at Göttingen. Tammannstraße 2, 37077 Göttingen, Germany / Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. Belo Horizonte, MG, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universit¨at Göttingen. Tammannstraße 2, 37077 Göttingen, Germany / Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. 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 Göttingen, Germany.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen. Tammannstraße 2, 37077 Göttingen, Germany / DZHK (German Center for Cardiovascular Research). Potsdamer Strasse 58, 10785 Berlin, Germany.
Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. Belo Horizonte, MG, Brasil.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universit¨at Göttingen. Tammannstraße 2, 37077 Göttingen, Germany / Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. 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 Göttingen, Germany.
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen. Tammannstraße 2, 37077 Göttingen, Germany / DZHK (German Center for Cardiovascular Research). Potsdamer Strasse 58, 10785 Berlin, Germany.
Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. Belo Horizonte, MG, Brasil.
Resumen en ingles
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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