Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities

Detalhes bibliográficos
Autor(a) principal: Gomes, Sara L. S.
Data de Publicação: 2017
Outros Autores: Militão, Gardenia C. G., Costa, Arinice M., Pessoa, Cláudia Ó., Costa-Lotufo, Letícia V., Torres-Santos, Eduardo C., Costa, Paulo R. R., Silva, Alcides J. M. da, Cunha-Junior, Edézio F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da Universidade Federal do Ceará (UFC)
Texto Completo: http://www.repositorio.ufc.br/handle/riufc/27266
Resumo: A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N , N -diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.
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spelling Gomes, Sara L. S.Militão, Gardenia C. G.Costa, Arinice M.Pessoa, Cláudia Ó.Costa-Lotufo, Letícia V.Torres-Santos, Eduardo C.Costa, Paulo R. R.Silva, Alcides J. M. daCunha-Junior, Edézio F.2017-11-08T14:22:35Z2017-11-08T14:22:35Z2017GOMES, S. L. S. et al. Suzuki-Miyaura coupling between 3-Iodolawsone and Arylboronic acids. Synthesis of Lapachol analogues with antineoplastic and antileishmanial activities. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 8, p. 1573-1584, 2017.0103-5053http://www.repositorio.ufc.br/handle/riufc/27266A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N , N -diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.Journal of the Brazilian Chemical SocietyQuinonesQuinonasLevopropoxifenoSuzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleengreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccessLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/27266/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINAL2017_art_slsgomes.pdf2017_art_slsgomes.pdfapplication/pdf405092http://repositorio.ufc.br/bitstream/riufc/27266/1/2017_art_slsgomes.pdf32419c928ab5d636f69ae3f23ccd7713MD51riufc/272662019-10-17 14:17:32.37oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2019-10-17T17:17:32Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
title Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
spellingShingle Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
Gomes, Sara L. S.
Quinones
Quinonas
Levopropoxifeno
title_short Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
title_full Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
title_fullStr Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
title_full_unstemmed Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
title_sort Suzuki-Miyaura coupling between 3-Iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
author Gomes, Sara L. S.
author_facet Gomes, Sara L. S.
Militão, Gardenia C. G.
Costa, Arinice M.
Pessoa, Cláudia Ó.
Costa-Lotufo, Letícia V.
Torres-Santos, Eduardo C.
Costa, Paulo R. R.
Silva, Alcides J. M. da
Cunha-Junior, Edézio F.
author_role author
author2 Militão, Gardenia C. G.
Costa, Arinice M.
Pessoa, Cláudia Ó.
Costa-Lotufo, Letícia V.
Torres-Santos, Eduardo C.
Costa, Paulo R. R.
Silva, Alcides J. M. da
Cunha-Junior, Edézio F.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Gomes, Sara L. S.
Militão, Gardenia C. G.
Costa, Arinice M.
Pessoa, Cláudia Ó.
Costa-Lotufo, Letícia V.
Torres-Santos, Eduardo C.
Costa, Paulo R. R.
Silva, Alcides J. M. da
Cunha-Junior, Edézio F.
dc.subject.por.fl_str_mv Quinones
Quinonas
Levopropoxifeno
topic Quinones
Quinonas
Levopropoxifeno
description A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N , N -diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.
publishDate 2017
dc.date.accessioned.fl_str_mv 2017-11-08T14:22:35Z
dc.date.available.fl_str_mv 2017-11-08T14:22:35Z
dc.date.issued.fl_str_mv 2017
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv GOMES, S. L. S. et al. Suzuki-Miyaura coupling between 3-Iodolawsone and Arylboronic acids. Synthesis of Lapachol analogues with antineoplastic and antileishmanial activities. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 8, p. 1573-1584, 2017.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/27266
dc.identifier.issn.none.fl_str_mv 0103-5053
identifier_str_mv GOMES, S. L. S. et al. Suzuki-Miyaura coupling between 3-Iodolawsone and Arylboronic acids. Synthesis of Lapachol analogues with antineoplastic and antileishmanial activities. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 8, p. 1573-1584, 2017.
0103-5053
url http://www.repositorio.ufc.br/handle/riufc/27266
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Journal of the Brazilian Chemical Society
publisher.none.fl_str_mv Journal of the Brazilian Chemical Society
dc.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Ceará (UFC)
instname:Universidade Federal do Ceará (UFC)
instacron:UFC
instname_str Universidade Federal do Ceará (UFC)
instacron_str UFC
institution UFC
reponame_str Repositório Institucional da Universidade Federal do Ceará (UFC)
collection Repositório Institucional da Universidade Federal do Ceará (UFC)
bitstream.url.fl_str_mv http://repositorio.ufc.br/bitstream/riufc/27266/2/license.txt
http://repositorio.ufc.br/bitstream/riufc/27266/1/2017_art_slsgomes.pdf
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repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)
repository.mail.fl_str_mv bu@ufc.br || repositorio@ufc.br
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