Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012001200016 |
Resumo: | In this work we report a versatile synthesis of fourteen γ-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 µmol L-1). In general, α,β-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76% of inhibition in 1000 µmol L-1. The results indicate that regardless of saturation, the presence of the γ-lactone moiety is important for the bioactivity, but their presence has no implications with potency. |
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Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-onesγ-lactoneswheat coleoptilesherbicideTriticum aestivumIn this work we report a versatile synthesis of fourteen γ-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 µmol L-1). In general, α,β-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76% of inhibition in 1000 µmol L-1. The results indicate that regardless of saturation, the presence of the γ-lactone moiety is important for the bioactivity, but their presence has no implications with potency.Sociedade Brasileira de Química2012-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012001200016Journal of the Brazilian Chemical Society v.23 n.12 2012reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532012001200016info:eu-repo/semantics/openAccessResende,Gabriela C.Alvarenga,Elson S.Galindo,Juan C. G.Macias,Francisco A.eng2013-02-08T00:00:00Zoai:scielo:S0103-50532012001200016Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-02-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
title |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
spellingShingle |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones Resende,Gabriela C. γ-lactones wheat coleoptiles herbicide Triticum aestivum |
title_short |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
title_full |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
title_fullStr |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
title_full_unstemmed |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
title_sort |
Synthesis and phytotoxicity of 4,5 functionalized tetrahydrofuran-2-ones |
author |
Resende,Gabriela C. |
author_facet |
Resende,Gabriela C. Alvarenga,Elson S. Galindo,Juan C. G. Macias,Francisco A. |
author_role |
author |
author2 |
Alvarenga,Elson S. Galindo,Juan C. G. Macias,Francisco A. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Resende,Gabriela C. Alvarenga,Elson S. Galindo,Juan C. G. Macias,Francisco A. |
dc.subject.por.fl_str_mv |
γ-lactones wheat coleoptiles herbicide Triticum aestivum |
topic |
γ-lactones wheat coleoptiles herbicide Triticum aestivum |
description |
In this work we report a versatile synthesis of fourteen γ-lactones all structurally related, nine of which are novel compounds, accomplished from the readily available furfural. The phytotoxic activity of the synthesized compounds was evaluated in vitro by the influence on the growth of wheat coleoptiles. The percentages of inhibition were mostly small and not statistically different from control after the third dilution (100 µmol L-1). In general, α,β-unsaturated lactones presented better activities than the saturated ones. The most active compounds presented 51, 68 and 76% of inhibition in 1000 µmol L-1. The results indicate that regardless of saturation, the presence of the γ-lactone moiety is important for the bioactivity, but their presence has no implications with potency. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-12-01 |
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=S0103-50532012001200016 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012001200016 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532012001200016 |
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 |
Journal of the Brazilian Chemical Society v.23 n.12 2012 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318174029479936 |