Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents

Detalhes bibliográficos
Autor(a) principal: Ferreira, Sabrina B.
Data de Publicação: 2010
Outros Autores: Silva, Fernando de Carvalho da, Bezerra, Flávio A. F. M. B., Lourenço, Maria C. S., Kaiser, Carlos R., Pinto, Angelo C., 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/37352
Resumo: 2020-11-25
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spelling Ferreira, Sabrina B.Silva, Fernando de Carvalho daBezerra, Flávio A. F. M. B.Lourenço, Maria C. S.Kaiser, Carlos R.Pinto, Angelo C.Ferreira, Vitor F.2019-11-25T14:16:02Z2019-11-25T14:16:02Z2010FERREIRA, Sabrina B. et al. Synthesis of alpha- and beta-pyran naphthoquinones as a new class of antitubercular agents. Archiv der Pharmazie - Chemistry in Life Sciences, v. 343, p. 81-90, 2010.0365-6233https://www.arca.fiocruz.br/handle/icict/3735210.1002/ardp.2009001621521-4184engWiley-VCH VerlagSynthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agentsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-11-25Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Ressonância Magnética Nuclear de Sólidos. Rio de Janeiro, RJ, Brasil / Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Ressonância Magnética Nuclear de Sólidos. Rio de Janeiro, RJ, Brasil / Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Clínica Evandro Chagas. Laboratório de Bacteriologia e Bioensaios em Micobactérias. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisa Clínica Evandro Chagas. Laboratório de Bacteriologia e Bioensaios em Micobactérias. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Ressonância Magnética Nuclear de Sólidos. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Ressonância Magnética Nuclear de Sólidos. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Niterói, RJ, Brasil.A series of α,- and β-pyran naphthoquinones (lapachones) have been synthesized and evaluated for their in-vitro antibacterial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar-Blue susceptibility test; the activity was expressed as the minimum inhibitory concentration (MIC) in lg/mL. The synthetic methodology consisted of the formation of methylene and aryl o-quinone methides (o-QMs) generated by Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with formaldehyde and arylaldehydes. These o-QMs then undergo facile hetero Diels –Alder reactions with dienophiles in aqueous ethanol media. Some naphthoquinones exhibited inhibition with MIC values of 1.25 lg/mL, similar to that of pharmaceutical concentrations currently used in tuberculosis treatment. These results justify further research into the value of these quinones as part of an original treatment for tuberculosis.LapachonesNaphthoquinonesSynthesisTuberculostaticsinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/37352/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Ferreira_Sabrina_etal_INI_2010.pdfve_Ferreira_Sabrina_etal_INI_2010.pdfapplication/pdf583267https://www.arca.fiocruz.br/bitstream/icict/37352/2/ve_Ferreira_Sabrina_etal_INI_2010.pdf04fd3de261d17cdde61572cdd454054fMD52TEXTve_Ferreira_Sabrina_etal_INI_2010.pdf.txtve_Ferreira_Sabrina_etal_INI_2010.pdf.txtExtracted texttext/plain49491https://www.arca.fiocruz.br/bitstream/icict/37352/3/ve_Ferreira_Sabrina_etal_INI_2010.pdf.txt6514cabd195368d15c74bf521a7da7b1MD53icict/373522021-03-24 16:32:39.61oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:39Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
title Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
spellingShingle Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
Ferreira, Sabrina B.
Lapachones
Naphthoquinones
Synthesis
Tuberculostatics
title_short Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
title_full Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
title_fullStr Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
title_full_unstemmed Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
title_sort Synthesis of α-and-β pyran naphthoquinones as a new class of antitubercular agents
author Ferreira, Sabrina B.
author_facet Ferreira, Sabrina B.
Silva, Fernando de Carvalho da
Bezerra, Flávio A. F. M. B.
Lourenço, Maria C. S.
Kaiser, Carlos R.
Pinto, Angelo C.
Ferreira, Vitor F.
author_role author
author2 Silva, Fernando de Carvalho da
Bezerra, Flávio A. F. M. B.
Lourenço, Maria C. S.
Kaiser, Carlos R.
Pinto, Angelo C.
Ferreira, Vitor F.
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Ferreira, Sabrina B.
Silva, Fernando de Carvalho da
Bezerra, Flávio A. F. M. B.
Lourenço, Maria C. S.
Kaiser, Carlos R.
Pinto, Angelo C.
Ferreira, Vitor F.
dc.subject.en.pt_BR.fl_str_mv Lapachones
Naphthoquinones
Synthesis
Tuberculostatics
topic Lapachones
Naphthoquinones
Synthesis
Tuberculostatics
description 2020-11-25
publishDate 2010
dc.date.issued.fl_str_mv 2010
dc.date.accessioned.fl_str_mv 2019-11-25T14:16:02Z
dc.date.available.fl_str_mv 2019-11-25T14:16:02Z
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 FERREIRA, Sabrina B. et al. Synthesis of alpha- and beta-pyran naphthoquinones as a new class of antitubercular agents. Archiv der Pharmazie - Chemistry in Life Sciences, v. 343, p. 81-90, 2010.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/37352
dc.identifier.issn.pt_BR.fl_str_mv 0365-6233
dc.identifier.doi.none.fl_str_mv 10.1002/ardp.200900162
dc.identifier.eissn.none.fl_str_mv 1521-4184
identifier_str_mv FERREIRA, Sabrina B. et al. Synthesis of alpha- and beta-pyran naphthoquinones as a new class of antitubercular agents. Archiv der Pharmazie - Chemistry in Life Sciences, v. 343, p. 81-90, 2010.
0365-6233
10.1002/ardp.200900162
1521-4184
url https://www.arca.fiocruz.br/handle/icict/37352
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-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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