Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/15913
Title: Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety
Authors: Diogo, Emilay B. T.
Dias, Gleiston G.
Rodrigues, Bernardo L.
Guimarães, Tiago T.
Valença, Wagner O.
Camara, Celso A.
Oliveira, Ronaldo N. de
Silva, Mauro G. da
Ferreira, Vitor F.
Paiva, Yen Galdino de
Goulart, Marilia O. F.
Menna-Barreto, Rubem F. S.
Castro, Solange L.. de
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 Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal do Rio de Janeiro. Núcleo de Pesquisa de Produtos Naturais. Rio de Janeiro, RJ, Brasil.
Universidade Federal Rural de Pernambuco. Departamento de Ciências Moleculares. Recife, PE, Brasil.
Universidade Federal Rural de Pernambuco. Departamento de Ciências Moleculares. Recife, PE, Brasil.
Universidade Federal de Pernambuco - UFPE. Recife, PE, Brasil.
Universidade Federal Fluminense. Instituto de Química. Niterói, RJ, 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
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.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Abstract: In our continued search for novel trypanocidal compounds, twenty-six derivatives of para- and orthonaphthoquinones coupled to 1,2,3-triazoles were synthesized. These compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Compounds 17–24, 28–30 and 36–38 are described herein for the first time. Three of these novel compounds (28–30) were found to be more potent than the standard drug benznidazole, with IC50/24 h values between 6.8 and 80.8 lM. Analysis of the toxicity to heart muscle cells led to LC50/24 h of <125, 63.1 and 281.6 lM for 28, 29 and 30, respectively. Displaying a selectivity index of 34.3, compound 30 will be further evaluated in vivo. The electrochemical properties of selected compounds were evaluated in an attempt to find correlations with trypanocidal activity, and it was observed that more electrophilic quinones were generally more potent.
Keywords: Lapachol
b-Lapachone
Quinone
Chagas disease
Trypomastigote
Click chemistry
Electrochemical parameters
keywords: Doença de Chagas
Quinona
Química Click
Tripomastigota
Parâmetros eletroquímicos
Issue Date: 2013
Publisher: open access
Citation: DIOGO, Emilay B. T. et al. Synthesis and anti-Trypanosoma cruzi activity of naphthoquinone-containing triazoles: Electrochemical studies on the effects of the quinoidal moiety. Bioorganic & Medicinal Chemistry, v.21, n.21, p.6337-6348, Nov. 2013.
DOI: 10.1016/j.bmc.2013.08.055
ISSN: 0968-0896
Copyright: restricted access
Appears in Collections:IOC - Artigos de Periódicos

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