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

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 y...

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Detalhes bibliográficos
Autores: dos Santos, Eric F. S., Cury, Nathalia M., do Nascimento, Tainara A., Raminelli, Cristiano [UNIFESP], Casagrande, Gleison A., Pereira, Claudio M. P., Simionatto, Euclesio, Yunes, Jose A., Pizzuti, Lucas
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:Brasil
Recursos:Universidade Federal de São Paulo (UNIFESP)
Repositorio:Repositório Institucional da UNIFESP
Idioma:inglés
OAI Identifier:oai:repositorio.unifesp.br:11600/55181
Acesso em linha:http://dx.doi.org/10.5935/0103-5053.20160166
https://repositorio.unifesp.br/handle/11600/55181
Access Level:acceso abierto
Palavra-chave:amidinopyrazole
pyrazoline
cytotoxic activity
leukemia
ultrasonic irradiation
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spelling Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides 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 RS411 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 mu mol L-1 and five compounds presented IC50 values around 40 mu mol L-1 for at least one of the three cell lines analyzed. One compound was not significantly cytotoxic, presenting IC50 value > 100 mu mol L- 1.Fundacao Univ Fed Grande Dourados, Grp Pesquisa Sintese & Caracterizacao Mol MS, Rua Joao Rosa Goes 1761, BR-79825070 Dourados, MS, BrazilUniv Estadual Campinas, Inst Biol, Dept Genet & Biol Mol, Rua Monteiro Lobato 255, BR-13083970 Campinas, SP, BrazilCtr Infantil Boldrini, Mol Biol Lab, Rua Dr Gabriel Porto 1270, BR-13083210 Campinas, SP, BrazilUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP, BrazilUniv Fed Pelotas, Ctr Ciencias Quim Farmaceut & Alimentos, Lab Lipid & Bioorgan, Campus Univ, BR-96001900 Pelotas, RS, BrazilUniv Estadual Mato Grosso do Sul, Rua Emilio Mascolli 275, BR-79950000 Navirai, MS, BrazilUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP, BrazilWeb of ScienceConselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)Fundacao de Apoio ao Desenvolvimento do Ensino, Ciencia e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT)Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)FAPESPCNPqCNPq: 483021/2013-0FUNDECT: 0180/12FAPESP: 12/12802-1Soc Brasileira Quimica2020-07-17T14:03:08Z2020-07-17T14:03:08Z2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion217-224application/pdfhttp://dx.doi.org/10.5935/0103-5053.20160166Journal Of The Brazilian Chemical Society. Sao Paulo, v. 28, n. 2, p. 217-224 2017.10.5935/0103-5053.20160166WOS000394031600003.pdf0103-5053https://repositorio.unifesp.br/handle/11600/55181WOS:000394031600003ark:/48912/001300002psxrengJournal Of The Brazilian Chemical SocietySao Pauloinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESPdos Santos, Eric F. S.Cury, Nathalia M.do Nascimento, Tainara A.Raminelli, Cristiano [UNIFESP]Casagrande, Gleison A.Pereira, Claudio M. P.Simionatto, EuclesioYunes, Jose A.Pizzuti, Lucas2024-08-11T06:09:27Zoai:repositorio.unifesp.br:11600/55181Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-08-11T06:09:27Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.none.fl_str_mv Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
spellingShingle Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
dos Santos, Eric F. S.
amidinopyrazole
pyrazoline
cytotoxic activity
leukemia
ultrasonic irradiation
title_short Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_full Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_fullStr Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_full_unstemmed Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
title_sort Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
dc.creator.none.fl_str_mv dos Santos, Eric F. S.
Cury, Nathalia M.
do Nascimento, Tainara A.
Raminelli, Cristiano [UNIFESP]
Casagrande, Gleison A.
Pereira, Claudio M. P.
Simionatto, Euclesio
Yunes, Jose A.
Pizzuti, Lucas
author dos Santos, Eric F. S.
author_facet dos Santos, Eric F. S.
Cury, Nathalia M.
do Nascimento, Tainara A.
Raminelli, Cristiano [UNIFESP]
Casagrande, Gleison A.
Pereira, Claudio M. P.
Simionatto, Euclesio
Yunes, Jose A.
Pizzuti, Lucas
author_role author
author2 Cury, Nathalia M.
do Nascimento, Tainara A.
Raminelli, Cristiano [UNIFESP]
Casagrande, Gleison A.
Pereira, Claudio M. P.
Simionatto, Euclesio
Yunes, Jose A.
Pizzuti, Lucas
author2_role author
author
author
author
author
author
author
author
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
publishDate 2017
dc.date.none.fl_str_mv 2017
2020-07-17T14:03:08Z
2020-07-17T14:03:08Z
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://dx.doi.org/10.5935/0103-5053.20160166
Journal Of The Brazilian Chemical Society. Sao Paulo, v. 28, n. 2, p. 217-224 2017.
10.5935/0103-5053.20160166
WOS000394031600003.pdf
0103-5053
https://repositorio.unifesp.br/handle/11600/55181
WOS:000394031600003
dc.identifier.dark.fl_str_mv ark:/48912/001300002psxr
url http://dx.doi.org/10.5935/0103-5053.20160166
https://repositorio.unifesp.br/handle/11600/55181
identifier_str_mv Journal Of The Brazilian Chemical Society. Sao Paulo, v. 28, n. 2, p. 217-224 2017.
10.5935/0103-5053.20160166
WOS000394031600003.pdf
0103-5053
WOS:000394031600003
ark:/48912/001300002psxr
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal Of The Brazilian Chemical Society
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 217-224
application/pdf
dc.coverage.none.fl_str_mv Sao Paulo
dc.publisher.none.fl_str_mv Soc Brasileira Quimica
publisher.none.fl_str_mv Soc Brasileira Quimica
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv biblioteca.csp@unifesp.br
_version_ 1853670608745791488
score 15.198674

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