Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/23112
Title: Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones
Authors: Jardim, Guilherme A. M.
Silva, Thaissa L.
Goulart, Marilia O. F.
Simone, Carlos A. de
Barbosa, Juliana M. C.
Salomão, Kelly
Castro, Solange L. de
Bower, John F.
Silva Júnior, Eufrânio N. da
Affilliation: Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.
Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.
Universidade de São Paulo. Instituto de Física. Departamento de Física e Informática. São Carlos, SP, 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.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Celular. Rio de Janeiro, RJ. Brasil.
University of Bristol. School of Chemistry. Bristol, UK.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Abstract: Thirty four halogen and selenium-containing quinones, synthesized by rhodium-catalyzed C-H bond activation and palladium-catalyzed cross-coupling reactions, were evaluated against bloodstream trypomastigotes of T. cruzi. We have identified fifteen compounds with IC50/24 h values of less than 2 μM. Electrochemical studies on A-ring functionalized naphthoquinones were also performed aiming to correlate redox properties with trypanocidal activity. For instance, (E)-5-styryl-1,4-naphthoquinone 59 and 5,8-diiodo-1,4-naphthoquinone 3, which are around fifty fold more active than the standard drug benznidazole, are potential derivatives for further investigation. These compounds represent powerful new agents useful in Chagas disease therapy.
Keywords: C-H functionalization
Quinones
Chagas Disease
Trypanosoma cruzi
Electrochemistry
keywords: Doença de Huntington
Trypanosoma cruzi
Quinonas
Eletroquímica
Issue Date: 2017
Publisher: Elsevier
Citation: JARDIM, Guilherme A. M. et al. Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones. European Journal of Medicinal Chemistry, v.136, p.406-419, 2017.
DOI: 10.1016/j.ejmech.2017.05.011
ISSN: 0223-5234
Copyright: restricted access
Appears in Collections:IOC - Artigos de Periódicos

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