Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity

Detalhes bibliográficos
Autor(a) principal: Baeza,Evelyn
Data de Publicação: 2012
Outros Autores: Catalán,Karen, Peña-Cortés,Hugo, Espinoza,Luis, Villena,Joan, Carrasco,Héctor
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000300015
Resumo: Natural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using BF3∙Et2O as a catalyst. Furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. The compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of PC-3 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma, and Dermal Human Fibroblasts DHF. IC50 values were in the µM range.
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spelling Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activitysynthesisgeranylhydroquinonescytotoxic activityNatural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using BF3∙Et2O as a catalyst. Furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. The compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of PC-3 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma, and Dermal Human Fibroblasts DHF. IC50 values were in the µM range.Sociedade Brasileira de Química2012-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000300015Química Nova v.35 n.3 2012reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422012000300015info:eu-repo/semantics/openAccessBaeza,EvelynCatalán,KarenPeña-Cortés,HugoEspinoza,LuisVillena,JoanCarrasco,Héctoreng2012-04-24T00:00:00Zoai:scielo:S0100-40422012000300015Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2012-04-24T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
title Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
spellingShingle Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
Baeza,Evelyn
synthesis
geranylhydroquinones
cytotoxic activity
title_short Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
title_full Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
title_fullStr Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
title_full_unstemmed Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
title_sort Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity
author Baeza,Evelyn
author_facet Baeza,Evelyn
Catalán,Karen
Peña-Cortés,Hugo
Espinoza,Luis
Villena,Joan
Carrasco,Héctor
author_role author
author2 Catalán,Karen
Peña-Cortés,Hugo
Espinoza,Luis
Villena,Joan
Carrasco,Héctor
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Baeza,Evelyn
Catalán,Karen
Peña-Cortés,Hugo
Espinoza,Luis
Villena,Joan
Carrasco,Héctor
dc.subject.por.fl_str_mv synthesis
geranylhydroquinones
cytotoxic activity
topic synthesis
geranylhydroquinones
cytotoxic activity
description Natural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using BF3∙Et2O as a catalyst. Furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. The compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of PC-3 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma, and Dermal Human Fibroblasts DHF. IC50 values were in the µM range.
publishDate 2012
dc.date.none.fl_str_mv 2012-01-01
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=S0100-40422012000300015
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000300015
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0100-40422012000300015
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.35 n.3 2012
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
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