Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos

Detalhes bibliográficos
Autor(a) principal: Simone Z. Mairink
Data de Publicação: 2019
Outros Autores: Luiz Cláudio de Almeida Barbosa, Célia Maltha, Jodieh Varejão, Geane Oliveira, Jacqueline Takahashi, John Boukouvalas
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Institucional da UFMG
Texto Completo: https://doi.org/10.21577/0100-4042.20170368
http://hdl.handle.net/1843/59328
https://orcid.org/0000-0002-5395-9608
https://orcid.org/0000-0002-1138-3962
Resumo: CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
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spelling 2023-10-09T23:07:02Z2023-10-09T23:07:02Z2019426595606https://doi.org/10.21577/0100-4042.201703680100-4042http://hdl.handle.net/1843/59328https://orcid.org/0000-0002-5395-9608https://orcid.org/0000-0002-1138-3962CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas GeraisThe increasing number of antibiotic resistant microorganisms requires the development of new drugs. In this context, natural cadiolides are promising leads as they present potent antimicrobial activity and low cytotoxicity. In this work we report the synthesis of 21 new cadiolide analogues. The synthesis involved a Diels−Alder cycloaddition/ cycloreversion reaction between an oxazole and different ynones, affording four intermediate butenolides (14a-d) in 61-81% yield. These intermediates were subjected to a vinylogous Knoevenagel condensation, followed by demethylation of the methoxylated compounds, affording all 21 analogues in good yields. The antibiotic activity of all compounds was evaluated against a panel of five microorganisms. The bioassays on the microbial growth showed that the cadiolides are more active for Gram-positive than Gram-negative bacteria, and have low activity against the fungus C. albicans. The most active compounds (14b, 15b, 15c and 16e) were effective against S. aureus showing IC50 in the range of 1.8-6.0 µg mL-1. The results also indicated that the nature and position of substituent groups on the aromatic moieties have some effect on the activities.porUniversidade Federal de Minas GeraisUFMGBrasilICX - DEPARTAMENTO DE QUÍMICAQuímica NovaMicroorganismos patogênicosQuímicaCadiolidesButenolidesGrowth inhibitionPathogenic microorganismsInibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeosInhibitory effect on growth of pathogenic microorganisms induced by butenolides related to cadiolidesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.scielo.br/j/qn/a/gmRPdDLwzs6C7gRhNh4hGHL/Simone Z. MairinkLuiz Cláudio de Almeida BarbosaCélia MalthaJodieh VarejãoGeane OliveiraJacqueline TakahashiJohn Boukouvalasapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/59328/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALInibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos.pdfInibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos.pdfapplication/pdf590435https://repositorio.ufmg.br/bitstream/1843/59328/2/Inibi%c3%a7%c3%a3o%20do%20crescimento%20de%20microrganismos%20patog%c3%aanicos%20induzida%20por%20butenol%c3%addeos%20an%c3%a1logos%20aos%20cadiol%c3%addeos.pdfefff82693ea2407403fb741eb5a537efMD521843/593282023-10-09 20:07:02.199oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-10-09T23:07:02Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
dc.title.pt_BR.fl_str_mv Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
dc.title.alternative.pt_BR.fl_str_mv Inhibitory effect on growth of pathogenic microorganisms induced by butenolides related to cadiolides
title Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
spellingShingle Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
Simone Z. Mairink
Cadiolides
Butenolides
Growth inhibition
Pathogenic microorganisms
Microorganismos patogênicos
Química
title_short Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
title_full Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
title_fullStr Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
title_full_unstemmed Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
title_sort Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
author Simone Z. Mairink
author_facet Simone Z. Mairink
Luiz Cláudio de Almeida Barbosa
Célia Maltha
Jodieh Varejão
Geane Oliveira
Jacqueline Takahashi
John Boukouvalas
author_role author
author2 Luiz Cláudio de Almeida Barbosa
Célia Maltha
Jodieh Varejão
Geane Oliveira
Jacqueline Takahashi
John Boukouvalas
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Simone Z. Mairink
Luiz Cláudio de Almeida Barbosa
Célia Maltha
Jodieh Varejão
Geane Oliveira
Jacqueline Takahashi
John Boukouvalas
dc.subject.por.fl_str_mv Cadiolides
Butenolides
Growth inhibition
Pathogenic microorganisms
topic Cadiolides
Butenolides
Growth inhibition
Pathogenic microorganisms
Microorganismos patogênicos
Química
dc.subject.other.pt_BR.fl_str_mv Microorganismos patogênicos
Química
description CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
publishDate 2019
dc.date.issued.fl_str_mv 2019
dc.date.accessioned.fl_str_mv 2023-10-09T23:07:02Z
dc.date.available.fl_str_mv 2023-10-09T23:07:02Z
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.uri.fl_str_mv http://hdl.handle.net/1843/59328
dc.identifier.doi.pt_BR.fl_str_mv https://doi.org/10.21577/0100-4042.20170368
dc.identifier.issn.pt_BR.fl_str_mv 0100-4042
dc.identifier.orcid.pt_BR.fl_str_mv https://orcid.org/0000-0002-5395-9608
https://orcid.org/0000-0002-1138-3962
url https://doi.org/10.21577/0100-4042.20170368
http://hdl.handle.net/1843/59328
https://orcid.org/0000-0002-5395-9608
https://orcid.org/0000-0002-1138-3962
identifier_str_mv 0100-4042
dc.language.iso.fl_str_mv por
language por
dc.relation.ispartof.pt_BR.fl_str_mv Química Nova
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade Federal de Minas Gerais
dc.publisher.initials.fl_str_mv UFMG
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv ICX - DEPARTAMENTO DE QUÍMICA
publisher.none.fl_str_mv Universidade Federal de Minas Gerais
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFMG
instname:Universidade Federal de Minas Gerais (UFMG)
instacron:UFMG
instname_str Universidade Federal de Minas Gerais (UFMG)
instacron_str UFMG
institution UFMG
reponame_str Repositório Institucional da UFMG
collection Repositório Institucional da UFMG
bitstream.url.fl_str_mv https://repositorio.ufmg.br/bitstream/1843/59328/1/License.txt
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