Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G

Detalhes bibliográficos
Autor(a) principal: Cassamale,Tatiana B.
Data de Publicação: 2016
Outros Autores: Costa,Eduarda C., Carvalho,Diego B., Cassemiro,Nadla S., Tomazela,Carolina C., Marques,Maria C. S., Ojeda,Mariáh, Matos,Maria F. C., Albuquerque,Sérgio, Arruda,Carla C. P., Baroni,Adriano C. M.
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=S0103-50532016000701217
Resumo: Sixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92%. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC50) values of 1.1, 3.71 and 7.23 µM. One compound was highly active against Leishmania infantum, with an IC50 value of 5.2 µM, and one derivative showed an IC50 value of 28.6 µM against Trypanosoma cruzi trypomastigotes. Regarding structure-activity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.
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spelling Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G1,4-diaryl-1,2,3-triazole derivativetetrahydrofuran neolignanclick chemistryantitrypanosomatid activitySixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92%. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC50) values of 1.1, 3.71 and 7.23 µM. One compound was highly active against Leishmania infantum, with an IC50 value of 5.2 µM, and one derivative showed an IC50 value of 28.6 µM against Trypanosoma cruzi trypomastigotes. Regarding structure-activity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.Sociedade Brasileira de Química2016-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000701217Journal of the Brazilian Chemical Society v.27 n.7 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160017info:eu-repo/semantics/openAccessCassamale,Tatiana B.Costa,Eduarda C.Carvalho,Diego B.Cassemiro,Nadla S.Tomazela,Carolina C.Marques,Maria C. S.Ojeda,MariáhMatos,Maria F. C.Albuquerque,SérgioArruda,Carla C. P.Baroni,Adriano C. M.eng2016-07-26T00:00:00Zoai:scielo:S0103-50532016000701217Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-07-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
title Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
spellingShingle Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
Cassamale,Tatiana B.
1,4-diaryl-1,2,3-triazole derivative
tetrahydrofuran neolignan
click chemistry
antitrypanosomatid activity
title_short Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
title_full Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
title_fullStr Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
title_full_unstemmed Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
title_sort Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G
author Cassamale,Tatiana B.
author_facet Cassamale,Tatiana B.
Costa,Eduarda C.
Carvalho,Diego B.
Cassemiro,Nadla S.
Tomazela,Carolina C.
Marques,Maria C. S.
Ojeda,Mariáh
Matos,Maria F. C.
Albuquerque,Sérgio
Arruda,Carla C. P.
Baroni,Adriano C. M.
author_role author
author2 Costa,Eduarda C.
Carvalho,Diego B.
Cassemiro,Nadla S.
Tomazela,Carolina C.
Marques,Maria C. S.
Ojeda,Mariáh
Matos,Maria F. C.
Albuquerque,Sérgio
Arruda,Carla C. P.
Baroni,Adriano C. M.
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Cassamale,Tatiana B.
Costa,Eduarda C.
Carvalho,Diego B.
Cassemiro,Nadla S.
Tomazela,Carolina C.
Marques,Maria C. S.
Ojeda,Mariáh
Matos,Maria F. C.
Albuquerque,Sérgio
Arruda,Carla C. P.
Baroni,Adriano C. M.
dc.subject.por.fl_str_mv 1,4-diaryl-1,2,3-triazole derivative
tetrahydrofuran neolignan
click chemistry
antitrypanosomatid activity
topic 1,4-diaryl-1,2,3-triazole derivative
tetrahydrofuran neolignan
click chemistry
antitrypanosomatid activity
description Sixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92%. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC50) values of 1.1, 3.71 and 7.23 µM. One compound was highly active against Leishmania infantum, with an IC50 value of 5.2 µM, and one derivative showed an IC50 value of 28.6 µM against Trypanosoma cruzi trypomastigotes. Regarding structure-activity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.
publishDate 2016
dc.date.none.fl_str_mv 2016-06-01
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=S0103-50532016000701217
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000701217
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160017
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.27 n.7 2016
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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