Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties

Detalhes bibliográficos
Autor(a) principal: Veloso, Marcia P.
Data de Publicação: 2012
Outros Autores: Romeiro, Nelilma C., Silva, Gilberto M. S., Alves, Helio de M., Doriguetto, Antonio C., Ellena, Javier, Miranda, Ana L. P., Barreiro, Eliezer J., Fraga, Carlos A. M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/36440
Resumo: 2020-10-15
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spelling Veloso, Marcia P.Romeiro, Nelilma C.Silva, Gilberto M. S.Alves, Helio de M.Doriguetto, Antonio C.Ellena, JavierMiranda, Ana L. P.Barreiro, Eliezer J.Fraga, Carlos A. M.2019-10-15T13:55:23Z2019-10-15T13:55:23Z2012VELOSO, Marcia P. et al. Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties. Chirality, v. 24, p. 463-470, 2012.0899-0042https://www.arca.fiocruz.br/handle/icict/3644010.1002/chir.220161520-636XengWileySynthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory propertiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-10-15Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, Brasil.Universidade Federal do Rio de Janeiro. Macaé, RJ, Brasil.Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Ciências Biomédicas. Programa de Pós-Graduação em Farmacologia e Química Medicinal. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Pesquisa Clínica Evandro Chagas. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil.Universidade Federal de Alfenas. Instituto de Ciências Exatas. Alfenas, MG, Brasil.Universidade de São Paulo. Instituto de Física de São Carlos. São Carlos, SP, Brasil.Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Ciências Biomédicas. Programa de Pós-Graduação em Farmacologia e Química Medicinal. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Janeiro. Instituto de Ciências Biomédicas. Programa de Pós-Graduação em Farmacologia e Química Medicinal. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Faculdade de Farmácia. Laboratório de Avaliação e Síntese de Substâncias Bioativas. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Janeiro. Instituto de Ciências Biomédicas. Programa de Pós-Graduação em Farmacologia e Química Medicinal. Rio de Janeiro, RJ, Brasil.This work describes the atropisomeric relationships of 3-methyl-5-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1-phenyl-1H-pyrazol-4-amine (2d), which belongs to series 4-aminobipyra-zole derivatives designed as anti-inflammatory agents. The1H nuclear magnetic resonance spectraobtained in the presence of a chiral lanthanide shift salt associated to chiral high-performance liquidchromatography analysis, X-ray diffraction, and molecular modeling tools confirmed thatorthobis-functionalized bipyrazole2dexists as a mixture ofaR,aS-atropisomers. These results provideuseful information to understand the pharmacological profile of this derivative and of other 4-amino-bipyrazole analogs.BipyrazoleAtropisomerismAxial chiralityNonsteroidal anti-inflammatory drugsCelecoxibCOX inhibitorsinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/36440/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Veloso_Marcia_etal_INI_2012.pdfve_Veloso_Marcia_etal_INI_2012.pdfapplication/pdf362006https://www.arca.fiocruz.br/bitstream/icict/36440/2/ve_Veloso_Marcia_etal_INI_2012.pdf6046d1dfb14b20e65c12119bf9df3afbMD52TEXTve_Veloso_Marcia_etal_INI_2012.pdf.txtve_Veloso_Marcia_etal_INI_2012.pdf.txtExtracted texttext/plain34636https://www.arca.fiocruz.br/bitstream/icict/36440/3/ve_Veloso_Marcia_etal_INI_2012.pdf.txte2874e408ef595fc67a094f652737a9dMD53icict/364402021-03-24 16:32:37.516oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:37Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
title Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
spellingShingle Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
Veloso, Marcia P.
Bipyrazole
Atropisomerism
Axial chirality
Nonsteroidal anti-inflammatory drugs
Celecoxib
COX inhibitors
title_short Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
title_full Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
title_fullStr Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
title_full_unstemmed Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
title_sort Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties
author Veloso, Marcia P.
author_facet Veloso, Marcia P.
Romeiro, Nelilma C.
Silva, Gilberto M. S.
Alves, Helio de M.
Doriguetto, Antonio C.
Ellena, Javier
Miranda, Ana L. P.
Barreiro, Eliezer J.
Fraga, Carlos A. M.
author_role author
author2 Romeiro, Nelilma C.
Silva, Gilberto M. S.
Alves, Helio de M.
Doriguetto, Antonio C.
Ellena, Javier
Miranda, Ana L. P.
Barreiro, Eliezer J.
Fraga, Carlos A. M.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Veloso, Marcia P.
Romeiro, Nelilma C.
Silva, Gilberto M. S.
Alves, Helio de M.
Doriguetto, Antonio C.
Ellena, Javier
Miranda, Ana L. P.
Barreiro, Eliezer J.
Fraga, Carlos A. M.
dc.subject.en.pt_BR.fl_str_mv Bipyrazole
Atropisomerism
Axial chirality
Nonsteroidal anti-inflammatory drugs
Celecoxib
COX inhibitors
topic Bipyrazole
Atropisomerism
Axial chirality
Nonsteroidal anti-inflammatory drugs
Celecoxib
COX inhibitors
description 2020-10-15
publishDate 2012
dc.date.issued.fl_str_mv 2012
dc.date.accessioned.fl_str_mv 2019-10-15T13:55:23Z
dc.date.available.fl_str_mv 2019-10-15T13:55:23Z
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 VELOSO, Marcia P. et al. Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties. Chirality, v. 24, p. 463-470, 2012.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/36440
dc.identifier.issn.pt_BR.fl_str_mv 0899-0042
dc.identifier.doi.none.fl_str_mv 10.1002/chir.22016
dc.identifier.eissn.none.fl_str_mv 1520-636X
identifier_str_mv VELOSO, Marcia P. et al. Synthesis and characterization of the atropisomeric relationships of a substituted N-phenyl-bipyrazole derivative with anti-inflammatory properties. Chirality, v. 24, p. 463-470, 2012.
0899-0042
10.1002/chir.22016
1520-636X
url https://www.arca.fiocruz.br/handle/icict/36440
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 Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
instname_str Fundação Oswaldo Cruz (FIOCRUZ)
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collection Repositório Institucional da FIOCRUZ (ARCA)
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