A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines

Detalhes bibliográficos
Autor(a) principal: Han,Qing
Data de Publicação: 2019
Outros Autores: Yin,Zijian, Sui,Jingjiao, Wang,Qingming, Sun,Yaquan
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=S0103-50532019000701483
Resumo: A series of N-aryl-5,6,7,8-tetra-hydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines were synthesized in moderate to good yield by using a microwave-enhanced conditions. The selected compounds were evaluated for their cytotoxic effects (IC50 values) on human pulmonary carcinoma (A549), murine BALB/c spontaneous colon adenocarcinoma (CT26) and human hepatocellular liver carcinoma (HepG2) cell lines in vitro. Amongst these compounds, one compound was found to have the better cytotoxic activity with reference to the standard Erlotinib hydrochloride (Tarceva™) against A549 (IC50 = 16.06 ± 0.09 µM) and HepG2 (IC50 = 15.01 ± 0.31 µM) cell lines. Especially, two compounds showed best cytotoxic effects against CT26 (IC50 = 11.38 ± 0.44 µM) and HepG2 (IC50 = 8.51 ± 0.52 µM) cell lines, respectively. The preliminary structure-activity relationships were disclosed and the thieno[2,3-d] pyrimidine skeleton could be exploited to potential antitumor agents in the future.
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spelling A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-aminesthieno[2,3-d] pyrimidinemicrowave-enhancedGewald reactionDimroth rearrangementbiological evaluationA series of N-aryl-5,6,7,8-tetra-hydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines were synthesized in moderate to good yield by using a microwave-enhanced conditions. The selected compounds were evaluated for their cytotoxic effects (IC50 values) on human pulmonary carcinoma (A549), murine BALB/c spontaneous colon adenocarcinoma (CT26) and human hepatocellular liver carcinoma (HepG2) cell lines in vitro. Amongst these compounds, one compound was found to have the better cytotoxic activity with reference to the standard Erlotinib hydrochloride (Tarceva™) against A549 (IC50 = 16.06 ± 0.09 µM) and HepG2 (IC50 = 15.01 ± 0.31 µM) cell lines. Especially, two compounds showed best cytotoxic effects against CT26 (IC50 = 11.38 ± 0.44 µM) and HepG2 (IC50 = 8.51 ± 0.52 µM) cell lines, respectively. The preliminary structure-activity relationships were disclosed and the thieno[2,3-d] pyrimidine skeleton could be exploited to potential antitumor agents in the future.Sociedade Brasileira de Química2019-07-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000701483Journal of the Brazilian Chemical Society v.30 n.7 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190044info:eu-repo/semantics/openAccessHan,QingYin,ZijianSui,JingjiaoWang,QingmingSun,Yaquaneng2019-07-01T00:00:00Zoai:scielo:S0103-50532019000701483Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-07-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
title A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
spellingShingle A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
Han,Qing
thieno[2,3-d] pyrimidine
microwave-enhanced
Gewald reaction
Dimroth rearrangement
biological evaluation
title_short A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
title_full A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
title_fullStr A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
title_full_unstemmed A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
title_sort A Microwave-Enhanced Synthesis and Biological Evaluation of N-Aryl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines
author Han,Qing
author_facet Han,Qing
Yin,Zijian
Sui,Jingjiao
Wang,Qingming
Sun,Yaquan
author_role author
author2 Yin,Zijian
Sui,Jingjiao
Wang,Qingming
Sun,Yaquan
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Han,Qing
Yin,Zijian
Sui,Jingjiao
Wang,Qingming
Sun,Yaquan
dc.subject.por.fl_str_mv thieno[2,3-d] pyrimidine
microwave-enhanced
Gewald reaction
Dimroth rearrangement
biological evaluation
topic thieno[2,3-d] pyrimidine
microwave-enhanced
Gewald reaction
Dimroth rearrangement
biological evaluation
description A series of N-aryl-5,6,7,8-tetra-hydrobenzo[4,5]thieno[2,3-d ]pyrimidin-4-amines were synthesized in moderate to good yield by using a microwave-enhanced conditions. The selected compounds were evaluated for their cytotoxic effects (IC50 values) on human pulmonary carcinoma (A549), murine BALB/c spontaneous colon adenocarcinoma (CT26) and human hepatocellular liver carcinoma (HepG2) cell lines in vitro. Amongst these compounds, one compound was found to have the better cytotoxic activity with reference to the standard Erlotinib hydrochloride (Tarceva™) against A549 (IC50 = 16.06 ± 0.09 µM) and HepG2 (IC50 = 15.01 ± 0.31 µM) cell lines. Especially, two compounds showed best cytotoxic effects against CT26 (IC50 = 11.38 ± 0.44 µM) and HepG2 (IC50 = 8.51 ± 0.52 µM) cell lines, respectively. The preliminary structure-activity relationships were disclosed and the thieno[2,3-d] pyrimidine skeleton could be exploited to potential antitumor agents in the future.
publishDate 2019
dc.date.none.fl_str_mv 2019-07-01
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=S0103-50532019000701483
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000701483
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20190044
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.30 n.7 2019
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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