Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4

Detalhes bibliográficos
Autor(a) principal: Santos,Edson dos A. dos
Data de Publicação: 2013
Outros Autores: Prado,Paulo C., Carvalho,Wanderley R. de, Lima,Ricardo V. de, Beatriz,Adilson, Lima,Dênis P. de, Hamel,Ernest, Dyba,Marzena A., Albuquerque,Sergio
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014
Resumo: We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).
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spelling Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4combretastatin A-4antitubulin activityleishmanicidal activityWe extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).Sociedade Brasileira de Química2013-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014Química Nova v.36 n.2 2013reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422013000200014info:eu-repo/semantics/openAccessSantos,Edson dos A. dosPrado,Paulo C.Carvalho,Wanderley R. deLima,Ricardo V. deBeatriz,AdilsonLima,Dênis P. deHamel,ErnestDyba,Marzena A.Albuquerque,Sergioeng2013-03-18T00:00:00Zoai:scielo:S0100-40422013000200014Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2013-03-18T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
title Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
spellingShingle Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
Santos,Edson dos A. dos
combretastatin A-4
antitubulin activity
leishmanicidal activity
title_short Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
title_full Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
title_fullStr Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
title_full_unstemmed Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
title_sort Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4
author Santos,Edson dos A. dos
author_facet Santos,Edson dos A. dos
Prado,Paulo C.
Carvalho,Wanderley R. de
Lima,Ricardo V. de
Beatriz,Adilson
Lima,Dênis P. de
Hamel,Ernest
Dyba,Marzena A.
Albuquerque,Sergio
author_role author
author2 Prado,Paulo C.
Carvalho,Wanderley R. de
Lima,Ricardo V. de
Beatriz,Adilson
Lima,Dênis P. de
Hamel,Ernest
Dyba,Marzena A.
Albuquerque,Sergio
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Santos,Edson dos A. dos
Prado,Paulo C.
Carvalho,Wanderley R. de
Lima,Ricardo V. de
Beatriz,Adilson
Lima,Dênis P. de
Hamel,Ernest
Dyba,Marzena A.
Albuquerque,Sergio
dc.subject.por.fl_str_mv combretastatin A-4
antitubulin activity
leishmanicidal activity
topic combretastatin A-4
antitubulin activity
leishmanicidal activity
description We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).
publishDate 2013
dc.date.none.fl_str_mv 2013-01-01
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=S0100-40422013000200014
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422013000200014
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0100-40422013000200014
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.36 n.2 2013
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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