Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2012 |
| Outros Autores: | , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/19070 |
Resumo: | Universidade Federal do Rio de Janeiro. 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. |
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Barbosa, Maria Letícia de CastroRamos, Thiago José FigueiraArantes, Ana Carolina Santos deMartins, Marco AurélioSilva, Patrícia Machado Rodrigues eBarreiro, Eliezer J.Lima, Lídia Moreira2017-05-30T16:47:29Z2017-05-30T16:47:29Z2012BARBOSA, Maria Letícia de Castro; et al. Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response. Molecules, v.17, p.14651-14672, 2012.1420-3049https://www.arca.fiocruz.br/handle/icict/1907010.3390/molecules1712146511420-3049engMDPIInflamaçãoFosmetFator de Necrose Tumoral alfainflammationTNF-αLASSBio-468LASSBio-596;phthalimideSynthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory responseinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal do Rio de Janeiro. 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.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Inflamação. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Inflamação. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Inflamação. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Inflamação. Rio de Janeiro, RJ. Brasil.Universidade Federal do Rio de Janeiro. 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 do Rio de Janeiro. 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.In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439 (2e) stands out showing an in vitro anti-TNF-α effect similar to the standard thalidomide. The relevance of tetrafluorination of the phthalimide nucleus was also confirmed by the anti-inflammatory profile of 2e, through oral administration, in a murine model of pulmonary inflammation. The corresponding tetrafluorocarboxyamide metabolite LASSBio-1454 (15), generated from partial hydrolysis of the derivative 2e, presented a significant in vitro effect and a pronounced anti-inflammatory activity in vivo.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/19070/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALanacarolina_arantes_etal_IOC_2012.pdfanacarolina_arantes_etal_IOC_2012.pdfapplication/pdf929854https://www.arca.fiocruz.br/bitstream/icict/19070/2/anacarolina_arantes_etal_IOC_2012.pdf29e2604247cc5853904d75e856c86965MD52TEXTanacarolina_arantes_etal_IOC_2012.pdf.txtanacarolina_arantes_etal_IOC_2012.pdf.txtExtracted 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| dc.title.pt_BR.fl_str_mv |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| title |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| spellingShingle |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response Barbosa, Maria Letícia de Castro Inflamação Fosmet Fator de Necrose Tumoral alfa inflammation TNF-α LASSBio-468 LASSBio-596; phthalimide |
| title_short |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| title_full |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| title_fullStr |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| title_full_unstemmed |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| title_sort |
Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response |
| author |
Barbosa, Maria Letícia de Castro |
| author_facet |
Barbosa, Maria Letícia de Castro Ramos, Thiago José Figueira Arantes, Ana Carolina Santos de Martins, Marco Aurélio Silva, Patrícia Machado Rodrigues e Barreiro, Eliezer J. Lima, Lídia Moreira |
| author_role |
author |
| author2 |
Ramos, Thiago José Figueira Arantes, Ana Carolina Santos de Martins, Marco Aurélio Silva, Patrícia Machado Rodrigues e Barreiro, Eliezer J. Lima, Lídia Moreira |
| author2_role |
author author author author author author |
| dc.contributor.author.fl_str_mv |
Barbosa, Maria Letícia de Castro Ramos, Thiago José Figueira Arantes, Ana Carolina Santos de Martins, Marco Aurélio Silva, Patrícia Machado Rodrigues e Barreiro, Eliezer J. Lima, Lídia Moreira |
| dc.subject.other.pt_BR.fl_str_mv |
Inflamação Fosmet Fator de Necrose Tumoral alfa |
| topic |
Inflamação Fosmet Fator de Necrose Tumoral alfa inflammation TNF-α LASSBio-468 LASSBio-596; phthalimide |
| dc.subject.en.pt_BR.fl_str_mv |
inflammation TNF-α LASSBio-468 LASSBio-596; phthalimide |
| description |
Universidade Federal do Rio de Janeiro. 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. |
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2012 |
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2012 |
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2017-05-30T16:47:29Z |
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2017-05-30T16:47:29Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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BARBOSA, Maria Letícia de Castro; et al. Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response. Molecules, v.17, p.14651-14672, 2012. |
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https://www.arca.fiocruz.br/handle/icict/19070 |
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1420-3049 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/molecules171214651 |
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1420-3049 |
| identifier_str_mv |
BARBOSA, Maria Letícia de Castro; et al. Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response. Molecules, v.17, p.14651-14672, 2012. 1420-3049 10.3390/molecules171214651 |
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