Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados
Ano de defesa: | 2007 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/4301 |
Resumo: | The present work describes the synthesis of a new series of furan-3-carboxamides and 3-aminomethylenedihydrofuran-2-ones, through the reactions of 3-trichloroacetyl furan or furan-3-carbonyl chloride, and 3-trichloroacetyl-4,5-dihydrofuran respectively, with benzamidine, primary and secondary amines, in good yields (63-98%). The synthesis of furan-3-carboxamides, begins from the aromatization of 3-trichloroacetyl-4,5-dihydrofuran to 3-tricloroacetyl furan followed by the nucleophilic displacement of the trichloromethyl group or the corresponding carboxylic acid chloride by nitrogen-containing compounds. The 3-aminomethylenedihydro-furan-2-ones were obtained, from a simple methodology, in a single reaction step, by the addition reaction of amines to 3-tricloroacetyl-4,5-dihydrofuran, in the same molar quantities. The compounds were evaluated for their in vitro antimicrobial activity against a panel of microorganisms including yeasts, filamentous fungi, bacteria and alga. Some of the furan-3-carboxamides and trihalomethylated ethyl carbamates exhibited significant antimicrobial activity. The in vivo toxicity of a series of aminomethylenedihydrofuran-2-ones against Artemia salina was evaluated. The results exhibited significant activity for the compounds 3-N-2-1-benzyl-piperidin-4-ylethylaminemethylendihydrofuran-2-one and 6-(2-hydroxy-ethyl)-7-oxo-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, when compared with controls. |
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2017-05-162017-05-162007-03-02COELHO, Helena Sebastiany. Synthesis and biological activity of furan-3-carboxamides, 3-aminomethylenedihydro-furan-2-ones and trihalomethylated ethyl carbamates. 2007. 222 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007.http://repositorio.ufsm.br/handle/1/4301The present work describes the synthesis of a new series of furan-3-carboxamides and 3-aminomethylenedihydrofuran-2-ones, through the reactions of 3-trichloroacetyl furan or furan-3-carbonyl chloride, and 3-trichloroacetyl-4,5-dihydrofuran respectively, with benzamidine, primary and secondary amines, in good yields (63-98%). The synthesis of furan-3-carboxamides, begins from the aromatization of 3-trichloroacetyl-4,5-dihydrofuran to 3-tricloroacetyl furan followed by the nucleophilic displacement of the trichloromethyl group or the corresponding carboxylic acid chloride by nitrogen-containing compounds. The 3-aminomethylenedihydro-furan-2-ones were obtained, from a simple methodology, in a single reaction step, by the addition reaction of amines to 3-tricloroacetyl-4,5-dihydrofuran, in the same molar quantities. The compounds were evaluated for their in vitro antimicrobial activity against a panel of microorganisms including yeasts, filamentous fungi, bacteria and alga. Some of the furan-3-carboxamides and trihalomethylated ethyl carbamates exhibited significant antimicrobial activity. The in vivo toxicity of a series of aminomethylenedihydrofuran-2-ones against Artemia salina was evaluated. The results exhibited significant activity for the compounds 3-N-2-1-benzyl-piperidin-4-ylethylaminemethylendihydrofuran-2-one and 6-(2-hydroxy-ethyl)-7-oxo-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, when compared with controls.Este trabalho apresenta a síntese de furan-3-carboxamidas e 3-aminometilenodiidrofuran-2-onas, duas séries de compostos obtidos com bons rendimentos (63-98%) e inéditos na literatura. A síntese das furan-3-carboxamidas, iniciou com a aromatização de 3-tricloroacetil-4,5-diidrofurano a 3-tricloroacetil furano seguido por substituição do grupo triclorometil ou do correspondente cloreto de ácido carboxílico por grupos amino substituídos. As 3-aminometilenodiidrofuran-2-onas foram obtidas, através de uma metodologia simples, em um único passo reacional, a partir da reação entre aminas e 3-tricloroacetil-4,5-diidrofurano em quantidades equimolares. Os compostos si ntetizados foram avaliados para atividade antimicrobiana in vitro frente a um grupo de microrganismos incluindo fungos leveduriformes, fungos filamentosos, bactérias e uma espécie de alga. Alguns furan-3-carboxamidas e carbamatos de etila derivados de enaminonas trialometiladas exibiram significante atividade antimicrobiana. A toxicidade in vivo, foi avaliada para uma série de aminometilenodiidrofuran-2-onas frente à Artemia salina. Os resultados evidenciaram significativa atividade citotóxica para os compostos 3-N-2-1-benzilpiperidin-4-iletilaminometilenodiidrofuran-2-ona e ácido-6-(2-hidroxi-etil)-7-oxo-1,7-diidro-[1,2,4]triazolo[1,5-a]pirimidina-2-carboxílico, quando comparados aos padrões.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaSíntese químicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometiladosSynthesis and biological activity of furan-3-carboxamides, 3-aminomethylenedihydro-furan-2-ones and trihalomethylated ethyl carbamatesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Alves, Sydney Hartzhttp://lattes.cnpq.br/0330782478769631Barichello, Rosemariohttp://lattes.cnpq.br/8251059080103642Bonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Silva, Pedro Eduardo Almeida dahttp://lattes.cnpq.br/4577337828511155http://lattes.cnpq.br/8758638068826650Coelho, Helena Sebastiany100600000000400300500300300300300233dc1de-ab03-4f57-9b85-e40dc01a2d4f9d9a28ec-c00d-4909-8e56-1a4e69f5b2577928080e-16be-47fd-b0a3-6d394fcd82a72c6d17fe-bbd2-4df3-ac7e-1ef8328c80ce8c234091-0259-4703-a717-5d611977d5f149e1c22c-8c02-4773-ab86-232c78c6b475info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALHELENA COELHO.pdfapplication/pdf3585665http://repositorio.ufsm.br/bitstream/1/4301/1/HELENA%20COELHO.pdf6be3b83e6bf22efaf0ad5b1dc07a97a3MD511/43012023-01-05 08:24:04.463oai:repositorio.ufsm.br:1/4301Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-01-05T11:24:04Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
dc.title.alternative.eng.fl_str_mv |
Synthesis and biological activity of furan-3-carboxamides, 3-aminomethylenedihydro-furan-2-ones and trihalomethylated ethyl carbamates |
title |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
spellingShingle |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados Coelho, Helena Sebastiany Química Química orgânica Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
title_full |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
title_fullStr |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
title_full_unstemmed |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
title_sort |
Síntese e atividade biológica de furan-3-carboxamidas, 3-aminometilenodiidrofuran-2-onas e carbamatos de etila trialometilados |
author |
Coelho, Helena Sebastiany |
author_facet |
Coelho, Helena Sebastiany |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Alves, Sydney Hartz |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0330782478769631 |
dc.contributor.referee2.fl_str_mv |
Barichello, Rosemario |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/8251059080103642 |
dc.contributor.referee3.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee4.fl_str_mv |
Silva, Pedro Eduardo Almeida da |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/4577337828511155 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8758638068826650 |
dc.contributor.author.fl_str_mv |
Coelho, Helena Sebastiany |
contributor_str_mv |
Zanatta, Nilo Alves, Sydney Hartz Barichello, Rosemario Bonacorso, Helio Gauze Silva, Pedro Eduardo Almeida da |
dc.subject.por.fl_str_mv |
Química Química orgânica Síntese química |
topic |
Química Química orgânica Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present work describes the synthesis of a new series of furan-3-carboxamides and 3-aminomethylenedihydrofuran-2-ones, through the reactions of 3-trichloroacetyl furan or furan-3-carbonyl chloride, and 3-trichloroacetyl-4,5-dihydrofuran respectively, with benzamidine, primary and secondary amines, in good yields (63-98%). The synthesis of furan-3-carboxamides, begins from the aromatization of 3-trichloroacetyl-4,5-dihydrofuran to 3-tricloroacetyl furan followed by the nucleophilic displacement of the trichloromethyl group or the corresponding carboxylic acid chloride by nitrogen-containing compounds. The 3-aminomethylenedihydro-furan-2-ones were obtained, from a simple methodology, in a single reaction step, by the addition reaction of amines to 3-tricloroacetyl-4,5-dihydrofuran, in the same molar quantities. The compounds were evaluated for their in vitro antimicrobial activity against a panel of microorganisms including yeasts, filamentous fungi, bacteria and alga. Some of the furan-3-carboxamides and trihalomethylated ethyl carbamates exhibited significant antimicrobial activity. The in vivo toxicity of a series of aminomethylenedihydrofuran-2-ones against Artemia salina was evaluated. The results exhibited significant activity for the compounds 3-N-2-1-benzyl-piperidin-4-ylethylaminemethylendihydrofuran-2-one and 6-(2-hydroxy-ethyl)-7-oxo-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, when compared with controls. |
publishDate |
2007 |
dc.date.issued.fl_str_mv |
2007-03-02 |
dc.date.accessioned.fl_str_mv |
2017-05-16 |
dc.date.available.fl_str_mv |
2017-05-16 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
COELHO, Helena Sebastiany. Synthesis and biological activity of furan-3-carboxamides, 3-aminomethylenedihydro-furan-2-ones and trihalomethylated ethyl carbamates. 2007. 222 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4301 |
identifier_str_mv |
COELHO, Helena Sebastiany. Synthesis and biological activity of furan-3-carboxamides, 3-aminomethylenedihydro-furan-2-ones and trihalomethylated ethyl carbamates. 2007. 222 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007. |
url |
http://repositorio.ufsm.br/handle/1/4301 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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100600000000 |
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400 300 500 300 300 300 300 |
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Química |
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Universidade Federal de Santa Maria |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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