N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity

Detalhes bibliográficos
Autor(a) principal: Lima, Giselle Barbosa
Data de Publicação: 2017
Outros Autores: Pinto, Ligia S. da Silveira, Kaiser, Carlos R., Wardell, James L., Freitas, Caroline S. de, Vieira, Yasmine R., Marttorelli, Andressa, Cerbino Neto, José, Bozza, Patrícia Torres, Wardell, Solange M. S. V., Souza, Marcus V. N. de, Souza, Thiago Moreno L.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/17955
Resumo: Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.
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spelling Lima, Giselle BarbosaPinto, Ligia S. da SilveiraKaiser, Carlos R.Wardell, James L.Freitas, Caroline S. deVieira, Yasmine R.Marttorelli, AndressaCerbino Neto, JoséBozza, Patrícia TorresWardell, Solange M. S. V.Souza, Marcus V. N. deSouza, Thiago Moreno L.2017-03-07T12:04:07Z2017-03-07T12:04:07Z2017LIMA, Giselle Barbosa; et al. N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti- Zika virus activity. European Journal of Medicinal Chemistry, v.127, p. 434-441, 2017.0223-5234https://www.arca.fiocruz.br/handle/icict/1795510.1016/j.ejmech.2017.01.0071768-3254engElsevierZika VirusDerivados de quinolinaMétodo sonoquímicoZika VirusQuinoline derivativesSonochemical methodN-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleFundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Departamento de Química Orgânica. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Departamento de Química Orgânica. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil / University of Aberdeen. Department of Chemistry. Aberdeen, Scotland, UK.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, BrasilFundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, BrasilFundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. BrasilCHEMSOL. Aberdeen, Scotland, UK.Universidade Federal do Rio de Janeiro. Departamento de Química Orgânica. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.Zika virus (ZIKV), an emerging Flavivirus, was recently associated with severe neurological complications and congenital diseases. Therefore, development of antiviral agents capable of inhibiting ZIKV replication is urgent. Chloroquine is a molecule with a confirmed safety history for use with pregnant women, and has been found to exhibit anti-ZIKV activity at concentrations around 10 μM. This suggests that modifications to the chloroquine structure could be promising for obtaining more effective anti-ZIKV agents. Here, we report the ability of a series of N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives to inhibit ZIKV replication in vitro. We have found that the quinoline derivative, N-(2-((5-nitrofuran-2-yl)methylimino)ethyl)-7-chloroquinolin-4-amine, 40, was the most potent compound within this series, reducing ZIKV replication by 72% at 10 μM. Compound 40 exhibits an EC50 value of 0.8 ± 0.07 μM, compared to that of chloroquine of 12 ± 3.2 μM. Good activities were also obtained for other compounds, including those with aryl groups = phenyl, 4-fluorophenyl, 4-nitrophenyl, 2,6-dimethoxyphenyl, 3-pyridinyl and 5-nitrothien-2-yl. Syntheses of these quinoline derivatives have been obtained both by thermal and ultrasonic means. The ultrasonic method produced comparable yields to the thermal (reflux) method in very much shorter times 30-180 s compared to 30-180 min reactions times. These results indicate that this group of compounds is a good follow-up point for the potential discovery of new drugs against the Zika disease.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/17955/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALgisele2_lima_etal_IOC_2017.pdfgisele2_lima_etal_IOC_2017.pdfapplication/pdf573817https://www.arca.fiocruz.br/bitstream/icict/17955/2/gisele2_lima_etal_IOC_2017.pdff5103a459f205e62a4e5ede3eecfc534MD52TEXTgisele2_lima_etal_IOC_2017.pdf.txtgisele2_lima_etal_IOC_2017.pdf.txtExtracted texttext/plain45569https://www.arca.fiocruz.br/bitstream/icict/17955/3/gisele2_lima_etal_IOC_2017.pdf.txte0cd2313b7b171bd71d544b8bd9ac62dMD53icict/179552023-09-04 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dc.title.pt_BR.fl_str_mv N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
title N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
spellingShingle N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
Lima, Giselle Barbosa
Zika Virus
Derivados de quinolina
Método sonoquímico
Zika Virus
Quinoline derivatives
Sonochemical method
title_short N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
title_full N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
title_fullStr N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
title_full_unstemmed N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
title_sort N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity
author Lima, Giselle Barbosa
author_facet Lima, Giselle Barbosa
Pinto, Ligia S. da Silveira
Kaiser, Carlos R.
Wardell, James L.
Freitas, Caroline S. de
Vieira, Yasmine R.
Marttorelli, Andressa
Cerbino Neto, José
Bozza, Patrícia Torres
Wardell, Solange M. S. V.
Souza, Marcus V. N. de
Souza, Thiago Moreno L.
author_role author
author2 Pinto, Ligia S. da Silveira
Kaiser, Carlos R.
Wardell, James L.
Freitas, Caroline S. de
Vieira, Yasmine R.
Marttorelli, Andressa
Cerbino Neto, José
Bozza, Patrícia Torres
Wardell, Solange M. S. V.
Souza, Marcus V. N. de
Souza, Thiago Moreno L.
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Lima, Giselle Barbosa
Pinto, Ligia S. da Silveira
Kaiser, Carlos R.
Wardell, James L.
Freitas, Caroline S. de
Vieira, Yasmine R.
Marttorelli, Andressa
Cerbino Neto, José
Bozza, Patrícia Torres
Wardell, Solange M. S. V.
Souza, Marcus V. N. de
Souza, Thiago Moreno L.
dc.subject.other.pt_BR.fl_str_mv Zika Virus
Derivados de quinolina
Método sonoquímico
topic Zika Virus
Derivados de quinolina
Método sonoquímico
Zika Virus
Quinoline derivatives
Sonochemical method
dc.subject.en.pt_BR.fl_str_mv Zika Virus
Quinoline derivatives
Sonochemical method
description Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil / Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Rio de Janeiro, RJ, Brasil.
publishDate 2017
dc.date.accessioned.fl_str_mv 2017-03-07T12:04:07Z
dc.date.available.fl_str_mv 2017-03-07T12:04:07Z
dc.date.issued.fl_str_mv 2017
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv LIMA, Giselle Barbosa; et al. N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti- Zika virus activity. European Journal of Medicinal Chemistry, v.127, p. 434-441, 2017.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/17955
dc.identifier.issn.pt_BR.fl_str_mv 0223-5234
dc.identifier.doi.none.fl_str_mv 10.1016/j.ejmech.2017.01.007
dc.identifier.eissn.none.fl_str_mv 1768-3254
identifier_str_mv LIMA, Giselle Barbosa; et al. N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti- Zika virus activity. European Journal of Medicinal Chemistry, v.127, p. 434-441, 2017.
0223-5234
10.1016/j.ejmech.2017.01.007
1768-3254
url https://www.arca.fiocruz.br/handle/icict/17955
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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