Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent

Detalhes bibliográficos
Autor(a) principal: Gallardo, Hugo
Data de Publicação: 2007
Outros Autores: Conte, Gilmar, Bryk, Fernando, Lourenço, Maria Cristina S., Costa, Marilia S., Ferreira, Vitor F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/58217
Resumo: Este trabalho descreve a síntese e a caracterização de quatorze derivados do sistema 1-alquil-4-fenil-[1,2,3]-triazol, por uma metodologia regiosseletiva e eficiente. Esta metodologia consistiu em uma cicloadição 1,3-dipolar, catalisada por Cu(I), entre arilazidas e arilacetilenos terminais (click-reaction). Os compostos foram avaliados quanto a sua atividade antimicrobiana contra a bactéria resistente a múltiplos fármacos, Mycobacterium tuberculosis H37Rv, agente causador da tuberculose. Seis dos [1,2,3]-triazóis foram mais ativos contra o M. tuberculosis do que o etambutol, utilizado como controle positivo.
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spelling Gallardo, HugoConte, GilmarBryk, FernandoLourenço, Maria Cristina S.Costa, Marilia S.Ferreira, Vitor F.2023-05-09T02:15:59Z2023-05-09T02:15:59Z2007GALLARDO, Hugo et al. Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent. Journal of the Brazilian Chemical Society, v. 18, n. 6, p. 1285-1291, 2007.0103-5053https://www.arca.fiocruz.br/handle/icict/5821710.1590/S0103-505320070006000271678-4790Este trabalho descreve a síntese e a caracterização de quatorze derivados do sistema 1-alquil-4-fenil-[1,2,3]-triazol, por uma metodologia regiosseletiva e eficiente. Esta metodologia consistiu em uma cicloadição 1,3-dipolar, catalisada por Cu(I), entre arilazidas e arilacetilenos terminais (click-reaction). Os compostos foram avaliados quanto a sua atividade antimicrobiana contra a bactéria resistente a múltiplos fármacos, Mycobacterium tuberculosis H37Rv, agente causador da tuberculose. Seis dos [1,2,3]-triazóis foram mais ativos contra o M. tuberculosis do que o etambutol, utilizado como controle positivo.Fourteen small molar mass 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives were prepared using a straightforward and efficient method for the regioselective synthesis of [1,2,3]-triazoles and the compounds were screened for antimycobacterial activity against multiple-drug-resistant strains of Mycobacterium tuberculosis H37Rv. The synthetic methodology consisted of a Cu(I)-catalyzed 1,3-dipolar cycloaddition of aryl azides to terminal arylacetylenes (click-reaction). Six [1,2,3]-triazoles were found to be more active against M. tuberculosis than the positive control ethambutol.Universidade Federal de Santa Catarina. Departamento de Química. Florianópolis, SC, Brasil.Universidade Federal de Santa Catarina. Departamento de Química. Florianópolis, SC, Brasil.Universidade Federal de Santa Catarina. Departamento de Química. Florianópolis, SC, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Cínica Evandro Chagas. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Niterói, RJ, Brasil.engSociedade Brasileira de QuímicaSynthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agentinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleTuberculosisClick reaction1,2,3-triazolesinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZORIGINALve_Hugo_Gallardo_etal_INI_2007.pdfve_Hugo_Gallardo_etal_INI_2007.pdfapplication/pdf184994https://www.arca.fiocruz.br/bitstream/icict/58217/2/ve_Hugo_Gallardo_etal_INI_2007.pdfedd09ecda08392e3799bdfc4cc8aec96MD52LICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/58217/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51icict/582172023-05-08 23:19:13.335oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-05-09T02:19:13Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.en_US.fl_str_mv Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
title Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
spellingShingle Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
Gallardo, Hugo
Tuberculosis
Click reaction
1,2,3-triazoles
title_short Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
title_full Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
title_fullStr Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
title_full_unstemmed Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
title_sort Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent
author Gallardo, Hugo
author_facet Gallardo, Hugo
Conte, Gilmar
Bryk, Fernando
Lourenço, Maria Cristina S.
Costa, Marilia S.
Ferreira, Vitor F.
author_role author
author2 Conte, Gilmar
Bryk, Fernando
Lourenço, Maria Cristina S.
Costa, Marilia S.
Ferreira, Vitor F.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Gallardo, Hugo
Conte, Gilmar
Bryk, Fernando
Lourenço, Maria Cristina S.
Costa, Marilia S.
Ferreira, Vitor F.
dc.subject.en.en_US.fl_str_mv Tuberculosis
Click reaction
1,2,3-triazoles
topic Tuberculosis
Click reaction
1,2,3-triazoles
description Este trabalho descreve a síntese e a caracterização de quatorze derivados do sistema 1-alquil-4-fenil-[1,2,3]-triazol, por uma metodologia regiosseletiva e eficiente. Esta metodologia consistiu em uma cicloadição 1,3-dipolar, catalisada por Cu(I), entre arilazidas e arilacetilenos terminais (click-reaction). Os compostos foram avaliados quanto a sua atividade antimicrobiana contra a bactéria resistente a múltiplos fármacos, Mycobacterium tuberculosis H37Rv, agente causador da tuberculose. Seis dos [1,2,3]-triazóis foram mais ativos contra o M. tuberculosis do que o etambutol, utilizado como controle positivo.
publishDate 2007
dc.date.issued.fl_str_mv 2007
dc.date.accessioned.fl_str_mv 2023-05-09T02:15:59Z
dc.date.available.fl_str_mv 2023-05-09T02:15:59Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.citation.fl_str_mv GALLARDO, Hugo et al. Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent. Journal of the Brazilian Chemical Society, v. 18, n. 6, p. 1285-1291, 2007.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/58217
dc.identifier.issn.en_US.fl_str_mv 0103-5053
dc.identifier.doi.none.fl_str_mv 10.1590/S0103-50532007000600027
dc.identifier.eissn.none.fl_str_mv 1678-4790
identifier_str_mv GALLARDO, Hugo et al. Synthesis and Evaluation of 1-Alkyl-4-phenyl-[1,2,3]-triazole Derivatives as Antimycobacterial Agent. Journal of the Brazilian Chemical Society, v. 18, n. 6, p. 1285-1291, 2007.
0103-5053
10.1590/S0103-50532007000600027
1678-4790
url https://www.arca.fiocruz.br/handle/icict/58217
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dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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