The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents

Detalhes bibliográficos
Autor(a) principal: Santos,Margareth Rôse L.
Data de Publicação: 1997
Outros Autores: Barreiro,Eliezer J., Braz-Filho,Raimundo, Miranda,Ana Luisa P.
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=S0103-50531997000500007
Resumo: The synthesis and pharmacological profile as analgesic and anti-inflammatory agents of new isochromanylacetylarylhydrazone derivatives (3) are described in this paper. The synthetic route used in this work to construct the heterocyclic six member ring explored a Lewis acid-catalyzed cyclization process as the key step, which represents a modified Friedel-Crafts reaction. These new derivatives (3) were obtained in ca. 85 % overall yields from the starting material safrole (4), an abundant natural product isolated from Sassafras oil. The NMR spectral analysis of these new derivatives indicated, at the C=N double bond level, the diastereomeric nature in a 70:30 ratio, where the major compound is the (E)-isomer. The results obtained from the pharmacological evaluation of (3) using the carrageenan-induced rat paw edema test and the acetic acid solution-induced constrictions in mouse test, indicated the pharmacophoric nature of the acylarylhydrazone moiety to the analgesic activity observed in this series.The role of the aryl substituents in the bioactivity seems to indicate that the presence of hydrophobic groups may improve the analgesic profile. These new isochromanylacetylarylhydrazone derivatives (3) represent a new class of non-addictive analgesic agents.
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spelling The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agentsanalgesic agentsisochromanylacetylarylhydrazonesThe synthesis and pharmacological profile as analgesic and anti-inflammatory agents of new isochromanylacetylarylhydrazone derivatives (3) are described in this paper. The synthetic route used in this work to construct the heterocyclic six member ring explored a Lewis acid-catalyzed cyclization process as the key step, which represents a modified Friedel-Crafts reaction. These new derivatives (3) were obtained in ca. 85 % overall yields from the starting material safrole (4), an abundant natural product isolated from Sassafras oil. The NMR spectral analysis of these new derivatives indicated, at the C=N double bond level, the diastereomeric nature in a 70:30 ratio, where the major compound is the (E)-isomer. The results obtained from the pharmacological evaluation of (3) using the carrageenan-induced rat paw edema test and the acetic acid solution-induced constrictions in mouse test, indicated the pharmacophoric nature of the acylarylhydrazone moiety to the analgesic activity observed in this series.The role of the aryl substituents in the bioactivity seems to indicate that the presence of hydrophobic groups may improve the analgesic profile. These new isochromanylacetylarylhydrazone derivatives (3) represent a new class of non-addictive analgesic agents.Sociedade Brasileira de Química1997-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531997000500007Journal of the Brazilian Chemical Society v.8 n.5 1997reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50531997000500007info:eu-repo/semantics/openAccessSantos,Margareth Rôse L.Barreiro,Eliezer J.Braz-Filho,RaimundoMiranda,Ana Luisa P.eng2010-09-10T00:00:00Zoai:scielo:S0103-50531997000500007Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-09-10T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
title The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
spellingShingle The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
Santos,Margareth Rôse L.
analgesic agents
isochromanylacetylarylhydrazones
title_short The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
title_full The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
title_fullStr The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
title_full_unstemmed The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
title_sort The synthesis of new isochromanylacetylarylhydrazones designed as probable non-addictive analgesic agents
author Santos,Margareth Rôse L.
author_facet Santos,Margareth Rôse L.
Barreiro,Eliezer J.
Braz-Filho,Raimundo
Miranda,Ana Luisa P.
author_role author
author2 Barreiro,Eliezer J.
Braz-Filho,Raimundo
Miranda,Ana Luisa P.
author2_role author
author
author
dc.contributor.author.fl_str_mv Santos,Margareth Rôse L.
Barreiro,Eliezer J.
Braz-Filho,Raimundo
Miranda,Ana Luisa P.
dc.subject.por.fl_str_mv analgesic agents
isochromanylacetylarylhydrazones
topic analgesic agents
isochromanylacetylarylhydrazones
description The synthesis and pharmacological profile as analgesic and anti-inflammatory agents of new isochromanylacetylarylhydrazone derivatives (3) are described in this paper. The synthetic route used in this work to construct the heterocyclic six member ring explored a Lewis acid-catalyzed cyclization process as the key step, which represents a modified Friedel-Crafts reaction. These new derivatives (3) were obtained in ca. 85 % overall yields from the starting material safrole (4), an abundant natural product isolated from Sassafras oil. The NMR spectral analysis of these new derivatives indicated, at the C=N double bond level, the diastereomeric nature in a 70:30 ratio, where the major compound is the (E)-isomer. The results obtained from the pharmacological evaluation of (3) using the carrageenan-induced rat paw edema test and the acetic acid solution-induced constrictions in mouse test, indicated the pharmacophoric nature of the acylarylhydrazone moiety to the analgesic activity observed in this series.The role of the aryl substituents in the bioactivity seems to indicate that the presence of hydrophobic groups may improve the analgesic profile. These new isochromanylacetylarylhydrazone derivatives (3) represent a new class of non-addictive analgesic agents.
publishDate 1997
dc.date.none.fl_str_mv 1997-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531997000500007
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531997000500007
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50531997000500007
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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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.8 n.5 1997
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
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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
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