A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , , , , |
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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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:icict/38833Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=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 |
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por |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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FIOCRUZ |
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