Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents

Detalhes bibliográficos
Autor(a) principal: Haider,Norbert
Data de Publicação: 2014
Outros Autores: Marian,Brigitte, Nagel,Thomas, Tarnai,Markus, Tropper,Katharina
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=S0103-50532014001100006
Resumo: 1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine- or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.
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spelling Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agentscarbazoleselectrophilic substitutionbrominationnitrationantitumor activity1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine- or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.Sociedade Brasileira de Química2014-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014001100006Journal of the Brazilian Chemical Society v.25 n.11 2014reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20140178info:eu-repo/semantics/openAccessHaider,NorbertMarian,BrigitteNagel,ThomasTarnai,MarkusTropper,Katharinaeng2014-11-13T00:00:00Zoai:scielo:S0103-50532014001100006Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2014-11-13T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
title Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
spellingShingle Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
Haider,Norbert
carbazoles
electrophilic substitution
bromination
nitration
antitumor activity
title_short Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
title_full Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
title_fullStr Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
title_full_unstemmed Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
title_sort Electrophilic substitution of dimethyl 1-methylcarbazole-2,3-dicarboxylate: synthesis of new b-Fused carbazoles as potential antitumor agents
author Haider,Norbert
author_facet Haider,Norbert
Marian,Brigitte
Nagel,Thomas
Tarnai,Markus
Tropper,Katharina
author_role author
author2 Marian,Brigitte
Nagel,Thomas
Tarnai,Markus
Tropper,Katharina
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Haider,Norbert
Marian,Brigitte
Nagel,Thomas
Tarnai,Markus
Tropper,Katharina
dc.subject.por.fl_str_mv carbazoles
electrophilic substitution
bromination
nitration
antitumor activity
topic carbazoles
electrophilic substitution
bromination
nitration
antitumor activity
description 1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine- or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.
publishDate 2014
dc.date.none.fl_str_mv 2014-11-01
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=S0103-50532014001100006
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014001100006
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20140178
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.25 n.11 2014
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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