Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines

Detalhes bibliográficos
Autor(a) principal: Santos,Eric F. S. dos
Data de Publicação: 2017
Outros Autores: Cury,Nathália M., Nascimento,Tainara A. do, Raminelli,Cristiano, Casagrande,Gleison A., Pereira,Claudio M. P., Simionatto,Euclésio, Yunes,José A., Pizzuti,Lucas
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=S0103-50532017000200217
Resumo: 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4;11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 µmol L-1 and five compounds presented IC50 values around 40 µmol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 µmol L-1.
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spelling Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Linesamidinopyrazolepyrazolinecytotoxic activityleukemiaultrasonic irradiation3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4;11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 µmol L-1 and five compounds presented IC50 values around 40 µmol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 µmol L-1.Sociedade Brasileira de Química2017-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000200217Journal of the Brazilian Chemical Society v.28 n.2 2017reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160166info:eu-repo/semantics/openAccessSantos,Eric F. S. dosCury,Nathália M.Nascimento,Tainara A. doRaminelli,CristianoCasagrande,Gleison A.Pereira,Claudio M. P.Simionatto,EuclésioYunes,José A.Pizzuti,Lucaseng2017-01-10T00:00:00Zoai:scielo:S0103-50532017000200217Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-01-10T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
spellingShingle Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
Santos,Eric F. S. dos
amidinopyrazole
pyrazoline
cytotoxic activity
leukemia
ultrasonic irradiation
title_short Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_full Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_fullStr Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_full_unstemmed Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_sort Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
author Santos,Eric F. S. dos
author_facet Santos,Eric F. S. dos
Cury,Nathália M.
Nascimento,Tainara A. do
Raminelli,Cristiano
Casagrande,Gleison A.
Pereira,Claudio M. P.
Simionatto,Euclésio
Yunes,José A.
Pizzuti,Lucas
author_role author
author2 Cury,Nathália M.
Nascimento,Tainara A. do
Raminelli,Cristiano
Casagrande,Gleison A.
Pereira,Claudio M. P.
Simionatto,Euclésio
Yunes,José A.
Pizzuti,Lucas
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Santos,Eric F. S. dos
Cury,Nathália M.
Nascimento,Tainara A. do
Raminelli,Cristiano
Casagrande,Gleison A.
Pereira,Claudio M. P.
Simionatto,Euclésio
Yunes,José A.
Pizzuti,Lucas
dc.subject.por.fl_str_mv amidinopyrazole
pyrazoline
cytotoxic activity
leukemia
ultrasonic irradiation
topic amidinopyrazole
pyrazoline
cytotoxic activity
leukemia
ultrasonic irradiation
description 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamides were efficiently prepared through a cyclocondensation of thiophenylchalcones with aminoguanidine hydrochloride under ultrasonic conditions in the presence of KOH and ethanol as a green solvent in short reaction times (15-35 min) and good yields (62-95%). All compounds produced were evaluated against the human Jurkat and RS4;11 acute lymphoblastic leukemia cell lines of T- and B-cell origin, respectively, and the K562 myelogenous leukemia cell line. Six compounds presented half maximal inhibitory concentration (IC50) values around 15 µmol L-1 and five compounds presented IC50 values around 40 µmol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 µmol L-1.
publishDate 2017
dc.date.none.fl_str_mv 2017-02-01
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=S0103-50532017000200217
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000200217
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160166
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.28 n.2 2017
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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