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

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dc.creatorSimone Z. Mairink
dc.creatorLuiz Cláudio de Almeida Barbosa
dc.creatorCélia Maltha
dc.creatorJodieh Varejão
dc.creatorGeane Oliveira
dc.creatorJacqueline Takahashi
dc.creatorJohn Boukouvalas
dc.date.accessioned2023-10-09T23:07:02Z
dc.date.accessioned2025-09-09T00:49:12Z
dc.date.available2023-10-09T23:07:02Z
dc.date.issued2019
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.21577/0100-4042.20170368
dc.identifier.issn0100-4042
dc.identifier.urihttps://hdl.handle.net/1843/59328
dc.languagepor
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofQuímica Nova
dc.rightsAcesso Aberto
dc.subjectMicroorganismos patogênicos
dc.subjectQuímica
dc.subject.otherCadiolides
dc.subject.otherButenolides
dc.subject.otherGrowth inhibition
dc.subject.otherPathogenic microorganisms
dc.titleInibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
dc.title.alternativeInhibitory effect on growth of pathogenic microorganisms induced by butenolides related to cadiolides
dc.typeArtigo de periódico
local.citation.epage606
local.citation.issue6
local.citation.spage595
local.citation.volume42
local.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.
local.identifier.orcidhttps://orcid.org/0000-0002-5395-9608
local.identifier.orcidhttps://orcid.org/0000-0002-1138-3962
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.scielo.br/j/qn/a/gmRPdDLwzs6C7gRhNh4hGHL/

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