A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis

Detalhes bibliográficos
Autor(a) principal: Silva, Raphael S. F.
Data de Publicação: 2009
Outros Autores: Pinto, Maria do Carmo F. R., Goulart, Marília O. F., Souza Filho, José D. de, Neves Jr, Ivan, Lourenço, Maria Cristina S., Pinto, Antonio V.
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/38833
Resumo: 2020-12-26
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spelling Silva, Raphael S. F.Pinto, Maria do Carmo F. R.Goulart, Marília O. F.Souza Filho, José D. deNeves Jr, IvanLourenço, Maria Cristina S.Pinto, Antonio V.2019-12-26T13:47:51Z2019-12-26T13:47:51Z2009SILVA, Raphael S. F. et al. A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis. European Journal of Medicinal Chemistry, v. 44, p. 2334-2337, 2009.0223-5234https://www.arca.fiocruz.br/handle/icict/3883310.1016/j.ejmech.2008.06.0141768-3254porElsevierA macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-12-26Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Núcleo de Pesquisas de Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Núcleo de Pesquisas de Produtos Naturais. Rio de Janeiro, RJ, Brasil.Universidade Federal de Alagoas. Instituto de Química e Biotecnologia. Maceió, AL, Brasil.Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Clínica Evandro Chagas. Serviço de Bacteriologia. Setor de Testagem de Drogas. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Clínica Evandro Chagas. Serviço de Bacteriologia. Setor de Testagem de Drogas. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Centro de Ciências da Saúde. Núcleo de Pesquisas de Produtos Naturais. Rio de Janeiro, RJ, Brasil.We report here an alternative to the MCPBA or ozonolysis-based oxidation methods of quinoxaline-featuring compounds prepared from beta-lapachones. The use of peracetic acid allowed a simple preparation of the corresponding macrolactones by cleavage of the ring system. These lactones were evaluated for their antimycobacterial potential and compound 4 turned out to have an MIC of 0.62mg per mL on Mycocabter-iumtuberculosis H37Rv. These results justify further research into its value as a potential lead for an original treatment of tuberculosis.LapacholPhenazinesPeracetic acid oxidationMacrolactonesTuberculosisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/38833/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Silva_Raphael_etal_INI_2009.pdfve_Silva_Raphael_etal_INI_2009.pdfapplication/pdf177070https://www.arca.fiocruz.br/bitstream/icict/38833/2/ve_Silva_Raphael_etal_INI_2009.pdf648712adfeb92c3fccc785dbf43a3e50MD52TEXTve_Silva_Raphael_etal_INI_2009.pdf.txtve_Silva_Raphael_etal_INI_2009.pdf.txtExtracted texttext/plain14151https://www.arca.fiocruz.br/bitstream/icict/38833/3/ve_Silva_Raphael_etal_INI_2009.pdf.txt9a0bcd2d629525110c041c37fdaf7aa4MD53icict/388332021-03-24 16:32:40.914oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:40Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
title A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
spellingShingle A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
Silva, Raphael S. F.
Lapachol
Phenazines
Peracetic acid oxidation
Macrolactones
Tuberculosis
title_short A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
title_full A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
title_fullStr A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
title_full_unstemmed A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
title_sort A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
author Silva, Raphael S. F.
author_facet Silva, Raphael S. F.
Pinto, Maria do Carmo F. R.
Goulart, Marília O. F.
Souza Filho, José D. de
Neves Jr, Ivan
Lourenço, Maria Cristina S.
Pinto, Antonio V.
author_role author
author2 Pinto, Maria do Carmo F. R.
Goulart, Marília O. F.
Souza Filho, José D. de
Neves Jr, Ivan
Lourenço, Maria Cristina S.
Pinto, Antonio V.
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Silva, Raphael S. F.
Pinto, Maria do Carmo F. R.
Goulart, Marília O. F.
Souza Filho, José D. de
Neves Jr, Ivan
Lourenço, Maria Cristina S.
Pinto, Antonio V.
dc.subject.en.pt_BR.fl_str_mv Lapachol
Phenazines
Peracetic acid oxidation
Macrolactones
Tuberculosis
topic Lapachol
Phenazines
Peracetic acid oxidation
Macrolactones
Tuberculosis
description 2020-12-26
publishDate 2009
dc.date.issued.fl_str_mv 2009
dc.date.accessioned.fl_str_mv 2019-12-26T13:47:51Z
dc.date.available.fl_str_mv 2019-12-26T13:47:51Z
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 SILVA, Raphael S. F. et al. A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis. European Journal of Medicinal Chemistry, v. 44, p. 2334-2337, 2009.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/38833
dc.identifier.issn.pt_BR.fl_str_mv 0223-5234
dc.identifier.doi.none.fl_str_mv 10.1016/j.ejmech.2008.06.014
dc.identifier.eissn.none.fl_str_mv 1768-3254
identifier_str_mv SILVA, Raphael S. F. et al. A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis. European Journal of Medicinal Chemistry, v. 44, p. 2334-2337, 2009.
0223-5234
10.1016/j.ejmech.2008.06.014
1768-3254
url https://www.arca.fiocruz.br/handle/icict/38833
dc.language.iso.fl_str_mv por
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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 Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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