Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation

Detalhes bibliográficos
Autor(a) principal: David,Cibelle C.
Data de Publicação: 2019
Outros Autores: Lins,Antonio C. S., Silva,Tania M. S., Campos,Júlia F., Silva,Teresinha G., Militão,Gardenia C. G., Camara,Celso A.
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=S0103-50532019000100008
Resumo: A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methyl-butyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted to cytotoxic screening against three tumor cell lines presenting good to excellent cytotoxic profiles.
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spelling Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation1,4-naphthoquinones3-alkenyl-2-hydroxy-1,4-naphthoquinoneslawsoneKnoevenagel condensationcytotoxic evaluationA modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methyl-butyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted to cytotoxic screening against three tumor cell lines presenting good to excellent cytotoxic profiles.Sociedade Brasileira de Química2019-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000100008Journal of the Brazilian Chemical Society v.30 n.1 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180146info:eu-repo/semantics/openAccessDavid,Cibelle C.Lins,Antonio C. S.Silva,Tania M. S.Campos,Júlia F.Silva,Teresinha G.Militão,Gardenia C. G.Camara,Celso A.eng2019-01-07T00:00:00Zoai:scielo:S0103-50532019000100008Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-01-07T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
title Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
spellingShingle Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
David,Cibelle C.
1,4-naphthoquinones
3-alkenyl-2-hydroxy-1,4-naphthoquinones
lawsone
Knoevenagel condensation
cytotoxic evaluation
title_short Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
title_full Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
title_fullStr Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
title_full_unstemmed Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
title_sort Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation
author David,Cibelle C.
author_facet David,Cibelle C.
Lins,Antonio C. S.
Silva,Tania M. S.
Campos,Júlia F.
Silva,Teresinha G.
Militão,Gardenia C. G.
Camara,Celso A.
author_role author
author2 Lins,Antonio C. S.
Silva,Tania M. S.
Campos,Júlia F.
Silva,Teresinha G.
Militão,Gardenia C. G.
Camara,Celso A.
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv David,Cibelle C.
Lins,Antonio C. S.
Silva,Tania M. S.
Campos,Júlia F.
Silva,Teresinha G.
Militão,Gardenia C. G.
Camara,Celso A.
dc.subject.por.fl_str_mv 1,4-naphthoquinones
3-alkenyl-2-hydroxy-1,4-naphthoquinones
lawsone
Knoevenagel condensation
cytotoxic evaluation
topic 1,4-naphthoquinones
3-alkenyl-2-hydroxy-1,4-naphthoquinones
lawsone
Knoevenagel condensation
cytotoxic evaluation
description A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methyl-butyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted to cytotoxic screening against three tumor cell lines presenting good to excellent cytotoxic profiles.
publishDate 2019
dc.date.none.fl_str_mv 2019-01-01
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=S0103-50532019000100008
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000100008
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20180146
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.30 n.1 2019
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
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