New iodine derivatives of flavonol and isoflavone

Detalhes bibliográficos
Autor(a) principal: Carvalho,Mário G. de
Data de Publicação: 2009
Outros Autores: Silva,Virginia C. da, Silva,Tânia M.S. da, Camara,Celso A., Braz-Filho,Raimundo
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Anais da Academia Brasileira de Ciências (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652009000100004
Resumo: The reaction of the flavonol 3,7,3', 4'-tetra-O-methylquercetin (1) and of the isoflavone 7,4'-di-O-methylgenistein (2) with alkaline iodine in methanol afforded four new iodine derivatives: 8-iodo-5-hydroxy-3,7,3', 4'-tetramethoxy- flavone (1a) and 6-iodo-5-hydroxy-3,7,3', 4'-tetramethoxyflavone (1b) from 1; 2 afforded a mixture of two compounds, identified as a racemic mixture of (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-8-iodo-isoflavanone (2a) and (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-6,8-diiodo-isoflavanone (2b). The formation of these different products reveals a significant difference involving the chemical interaction between the reactive site of α, β-unsaturated ketones of flavonol and isoflavone under the tested reaction conditions (using I2/KOH/MeOH). Furthermore, the trans stereo selectivity is noteworthy in the nucleophylic addition of methanol at the isoflavone α, β-unsaturated system. The structures were identified on the basis of spectral data, mainly 1D and 2D NMR and mass spectra.
id ABC-1_1fef5d8b3efa829d584fdfff56fd6697
oai_identifier_str oai:scielo:S0001-37652009000100004
network_acronym_str ABC-1
network_name_str Anais da Academia Brasileira de Ciências (Online)
repository_id_str
spelling New iodine derivatives of flavonol and isoflavoneflavonolisoflavoneiodoflavonoidiodoisoflavonoidiodine derivativesThe reaction of the flavonol 3,7,3', 4'-tetra-O-methylquercetin (1) and of the isoflavone 7,4'-di-O-methylgenistein (2) with alkaline iodine in methanol afforded four new iodine derivatives: 8-iodo-5-hydroxy-3,7,3', 4'-tetramethoxy- flavone (1a) and 6-iodo-5-hydroxy-3,7,3', 4'-tetramethoxyflavone (1b) from 1; 2 afforded a mixture of two compounds, identified as a racemic mixture of (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-8-iodo-isoflavanone (2a) and (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-6,8-diiodo-isoflavanone (2b). The formation of these different products reveals a significant difference involving the chemical interaction between the reactive site of α, β-unsaturated ketones of flavonol and isoflavone under the tested reaction conditions (using I2/KOH/MeOH). Furthermore, the trans stereo selectivity is noteworthy in the nucleophylic addition of methanol at the isoflavone α, β-unsaturated system. The structures were identified on the basis of spectral data, mainly 1D and 2D NMR and mass spectra.Academia Brasileira de Ciências2009-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652009000100004Anais da Academia Brasileira de Ciências v.81 n.1 2009reponame:Anais da Academia Brasileira de Ciências (Online)instname:Academia Brasileira de Ciências (ABC)instacron:ABC10.1590/S0001-37652009000100004info:eu-repo/semantics/openAccessCarvalho,Mário G. deSilva,Virginia C. daSilva,Tânia M.S. daCamara,Celso A.Braz-Filho,Raimundoeng2009-02-19T00:00:00Zoai:scielo:S0001-37652009000100004Revistahttp://www.scielo.br/aabchttps://old.scielo.br/oai/scielo-oai.php||aabc@abc.org.br1678-26900001-3765opendoar:2009-02-19T00:00Anais da Academia Brasileira de Ciências (Online) - Academia Brasileira de Ciências (ABC)false
dc.title.none.fl_str_mv New iodine derivatives of flavonol and isoflavone
title New iodine derivatives of flavonol and isoflavone
spellingShingle New iodine derivatives of flavonol and isoflavone
Carvalho,Mário G. de
flavonol
isoflavone
iodoflavonoid
iodoisoflavonoid
iodine derivatives
title_short New iodine derivatives of flavonol and isoflavone
title_full New iodine derivatives of flavonol and isoflavone
title_fullStr New iodine derivatives of flavonol and isoflavone
title_full_unstemmed New iodine derivatives of flavonol and isoflavone
title_sort New iodine derivatives of flavonol and isoflavone
author Carvalho,Mário G. de
author_facet Carvalho,Mário G. de
Silva,Virginia C. da
Silva,Tânia M.S. da
Camara,Celso A.
Braz-Filho,Raimundo
author_role author
author2 Silva,Virginia C. da
Silva,Tânia M.S. da
Camara,Celso A.
Braz-Filho,Raimundo
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Carvalho,Mário G. de
Silva,Virginia C. da
Silva,Tânia M.S. da
Camara,Celso A.
Braz-Filho,Raimundo
dc.subject.por.fl_str_mv flavonol
isoflavone
iodoflavonoid
iodoisoflavonoid
iodine derivatives
topic flavonol
isoflavone
iodoflavonoid
iodoisoflavonoid
iodine derivatives
description The reaction of the flavonol 3,7,3', 4'-tetra-O-methylquercetin (1) and of the isoflavone 7,4'-di-O-methylgenistein (2) with alkaline iodine in methanol afforded four new iodine derivatives: 8-iodo-5-hydroxy-3,7,3', 4'-tetramethoxy- flavone (1a) and 6-iodo-5-hydroxy-3,7,3', 4'-tetramethoxyflavone (1b) from 1; 2 afforded a mixture of two compounds, identified as a racemic mixture of (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-8-iodo-isoflavanone (2a) and (±)-trans-5-hydroxy-2,3,7,4'-tetramethoxy-6,8-diiodo-isoflavanone (2b). The formation of these different products reveals a significant difference involving the chemical interaction between the reactive site of α, β-unsaturated ketones of flavonol and isoflavone under the tested reaction conditions (using I2/KOH/MeOH). Furthermore, the trans stereo selectivity is noteworthy in the nucleophylic addition of methanol at the isoflavone α, β-unsaturated system. The structures were identified on the basis of spectral data, mainly 1D and 2D NMR and mass spectra.
publishDate 2009
dc.date.none.fl_str_mv 2009-03-01
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=S0001-37652009000100004
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652009000100004
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0001-37652009000100004
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 Academia Brasileira de Ciências
publisher.none.fl_str_mv Academia Brasileira de Ciências
dc.source.none.fl_str_mv Anais da Academia Brasileira de Ciências v.81 n.1 2009
reponame:Anais da Academia Brasileira de Ciências (Online)
instname:Academia Brasileira de Ciências (ABC)
instacron:ABC
instname_str Academia Brasileira de Ciências (ABC)
instacron_str ABC
institution ABC
reponame_str Anais da Academia Brasileira de Ciências (Online)
collection Anais da Academia Brasileira de Ciências (Online)
repository.name.fl_str_mv Anais da Academia Brasileira de Ciências (Online) - Academia Brasileira de Ciências (ABC)
repository.mail.fl_str_mv ||aabc@abc.org.br
_version_ 1754302857224388608