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Please use this identifier to cite or link to this item: http://hdl.handle.net/1843/59328
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dc.creatorSimone Z. Mairinkpt_BR
dc.creatorLuiz Cláudio de Almeida Barbosapt_BR
dc.creatorCélia Malthapt_BR
dc.creatorJodieh Varejãopt_BR
dc.creatorGeane Oliveirapt_BR
dc.creatorJacqueline Takahashipt_BR
dc.creatorJohn Boukouvalaspt_BR
dc.date.accessioned2023-10-09T23:07:02Z-
dc.date.available2023-10-09T23:07:02Z-
dc.date.issued2019-
dc.citation.volume42pt_BR
dc.citation.issue6pt_BR
dc.citation.spage595pt_BR
dc.citation.epage606pt_BR
dc.identifier.doihttps://doi.org/10.21577/0100-4042.20170368pt_BR
dc.identifier.issn0100-4042pt_BR
dc.identifier.urihttp://hdl.handle.net/1843/59328-
dc.description.resumoThe 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.pt_BR
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Geraispt_BR
dc.format.mimetypepdfpt_BR
dc.languageporpt_BR
dc.publisherUniversidade Federal de Minas Geraispt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentICX - DEPARTAMENTO DE QUÍMICApt_BR
dc.publisher.initialsUFMGpt_BR
dc.relation.ispartofQuímica Novapt_BR
dc.rightsAcesso Abertopt_BR
dc.subjectCadiolidespt_BR
dc.subjectButenolidespt_BR
dc.subjectGrowth inhibitionpt_BR
dc.subjectPathogenic microorganismspt_BR
dc.subject.otherMicroorganismos patogênicospt_BR
dc.subject.otherQuímicapt_BR
dc.titleInibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeospt_BR
dc.title.alternativeInhibitory effect on growth of pathogenic microorganisms induced by butenolides related to cadiolidespt_BR
dc.typeArtigo de Periódicopt_BR
dc.url.externahttps://www.scielo.br/j/qn/a/gmRPdDLwzs6C7gRhNh4hGHL/pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-5395-9608pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-1138-3962pt_BR
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