Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019004600595 |
Resumo: | The 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. |
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Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeoscadiolidesbutenolidesgrowth inhibitionpathogenic microorganismsThe 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.Sociedade Brasileira de Química2019-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019004600595Química Nova v.42 n.6 2019reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0100-4042.20170368info:eu-repo/semantics/openAccessMairink,Simone Z.Barbosa,Luiz C. A.Maltha,Célia R. A.Varejão,Jodieh O. S.Oliveira,Geane P.Takahashi,Jacqueline A.Boukouvalas,Johnpor2019-08-12T00:00:00Zoai:scielo:S0100-40422019004600595Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2019-08-12T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Inibição do crescimento de microrganismos patogênicos induzida por butenolídeos análogos aos cadiolídeos |
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 Mairink,Simone Z. cadiolides butenolides growth inhibition pathogenic microorganisms |
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 |
Mairink,Simone Z. |
author_facet |
Mairink,Simone Z. Barbosa,Luiz C. A. Maltha,Célia R. A. Varejão,Jodieh O. S. Oliveira,Geane P. Takahashi,Jacqueline A. Boukouvalas,John |
author_role |
author |
author2 |
Barbosa,Luiz C. A. Maltha,Célia R. A. Varejão,Jodieh O. S. Oliveira,Geane P. Takahashi,Jacqueline A. Boukouvalas,John |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Mairink,Simone Z. Barbosa,Luiz C. A. Maltha,Célia R. A. Varejão,Jodieh O. S. Oliveira,Geane P. Takahashi,Jacqueline A. Boukouvalas,John |
dc.subject.por.fl_str_mv |
cadiolides butenolides growth inhibition pathogenic microorganisms |
topic |
cadiolides butenolides growth inhibition pathogenic microorganisms |
description |
The 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. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-06-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019004600595 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019004600595 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
10.21577/0100-4042.20170368 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Química Nova v.42 n.6 2019 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318119681785856 |