Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos

Detalhes bibliográficos
Ano de defesa: 2017
Autor(a) principal: Mayer, João Cândido Pilar lattes
Orientador(a): Dornelles, Luciano lattes
Banca de defesa: Iglesias, Bernanrdo Almeida lattes, Ilha, Vinicius lattes
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
Oxadiazóis
Ácidos acrílicos
Ferroceno
UV-Vis
Voltametria
Palavras-chave em Inglês:
Oxadiazoles
Acrylic acids
Ferrocene
UV-Vis
Voltammetry
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/13682
Resumo: A series of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles was synthesized through a one-pot condensation-cyclization reaction between 3-substituted acrylic acids and 5-aryl-1,2,4-oxadiazolyl-1,2,4-oxadiazoles, and were characterized through 1H NMR, 13C NMR, X-ray diffraction and HRMS. Products were obtained in rather variable yields (23 – 87 %). The cited compounds were compared to single heterocycle-containing (1,3,4-oxadiazole) examples in order to measure the influence of the 1,2,4-oxadiazole, as well as the substituents’, on the molecules. After a simple comparison of 1H NMR signs between cinnamic acid derivatives, two series of (E)-3-ferrocenylacrylic acid derivatives were characterized through UV-Vis spectroscopy and cyclic voltammetry. They were also tested for ct-DNA interaction, displaying strong interaction (K~106 M-1) with it. Finally, crotonic acid derivatives were reactive to the aminoacid cysteine, giving a series of adducts, which suggests a possible activity in future biological tests.
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spelling 2018-07-06T14:12:55Z2018-07-06T14:12:55Z2017-02-24http://repositorio.ufsm.br/handle/1/13682A series of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles was synthesized through a one-pot condensation-cyclization reaction between 3-substituted acrylic acids and 5-aryl-1,2,4-oxadiazolyl-1,2,4-oxadiazoles, and were characterized through 1H NMR, 13C NMR, X-ray diffraction and HRMS. Products were obtained in rather variable yields (23 – 87 %). The cited compounds were compared to single heterocycle-containing (1,3,4-oxadiazole) examples in order to measure the influence of the 1,2,4-oxadiazole, as well as the substituents’, on the molecules. After a simple comparison of 1H NMR signs between cinnamic acid derivatives, two series of (E)-3-ferrocenylacrylic acid derivatives were characterized through UV-Vis spectroscopy and cyclic voltammetry. They were also tested for ct-DNA interaction, displaying strong interaction (K~106 M-1) with it. Finally, crotonic acid derivatives were reactive to the aminoacid cysteine, giving a series of adducts, which suggests a possible activity in future biological tests.Uma série de 1,3,4-oxadiazolil-1,2,4-oxadiazóis foi sintetizada por meio de uma reação one-pot de condensação – ciclização entre ácidos acrílicos 3-substituídos e 3-aril-1,2,4-oxadiazol-5-carboidrazidas, e caracterizados por RMN de 1H, RMN de 13C, difração de raios-X e HRMS. Os produtos foram obtidos com rendimentos bastante variáveis (23 – 87 %). Os compostos mencionados foram comparados com exemplos contendo apenas uma unidade heterocíclica (1,3,4-oxadiazol) para se determinar a influência do 1,2,4-oxadiazol, bem como o efeito dos demais substituintes, sobre as moléculas. Após uma breve comparação de sinais de RMN de 1H entre derivados do ácido cinâmico, duas séries de derivados do ácido (E)-3-ferrocenilacrílico foram caracterizadas por espectroscopia UV-Vis e voltametria cíclica. Os mesmos também foram testados quanto à interação com ct-DNA, mostrando forte interação com este (K~106 M-1). Por fim, derivados de ácido crotônico apresentaram reatividade frente ao aminoácido cisteína, formando uma série de adutos, o que sugere possível atividade em futuros testes biológicos.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessOxadiazóisÁcidos acrílicosFerrocenoUV-VisVoltametriaOxadiazolesAcrylic acidsFerroceneUV-VisVoltammetryCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídosSynthesis and characterization of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles derived from 3-substituted acrylic acidsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisDornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Iglesias, Bernanrdo Almeidahttp://lattes.cnpq.br/4402375533322977Ilha, Viniciushttp://lattes.cnpq.br/3882671719676564http://lattes.cnpq.br/2787457529574646Mayer, João Cândido Pilar1006000000006006b4b1c8a-fdd1-49f0-a8ce-2d891b6579b620fb5647-f598-47ba-8c9e-b9d8ffa5fe75d26cc6fd-4ef1-4791-8bfd-3de478f44b837478688e-3aa2-4a32-9f0a-d2b661267e83reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMLICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
dc.title.alternative.eng.fl_str_mv Synthesis and characterization of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles derived from 3-substituted acrylic acids
title Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
spellingShingle Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
Mayer, João Cândido Pilar
Oxadiazóis
Ácidos acrílicos
Ferroceno
UV-Vis
Voltametria
Oxadiazoles
Acrylic acids
Ferrocene
UV-Vis
Voltammetry
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
title_full Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
title_fullStr Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
title_full_unstemmed Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
title_sort Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos
author Mayer, João Cândido Pilar
author_facet Mayer, João Cândido Pilar
author_role author
dc.contributor.advisor1.fl_str_mv Dornelles, Luciano
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/7629319262073140
dc.contributor.referee1.fl_str_mv Iglesias, Bernanrdo Almeida
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/4402375533322977
dc.contributor.referee2.fl_str_mv Ilha, Vinicius
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/3882671719676564
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/2787457529574646
dc.contributor.author.fl_str_mv Mayer, João Cândido Pilar
contributor_str_mv Dornelles, Luciano
Iglesias, Bernanrdo Almeida
Ilha, Vinicius
dc.subject.por.fl_str_mv Oxadiazóis
Ácidos acrílicos
Ferroceno
UV-Vis
Voltametria
topic Oxadiazóis
Ácidos acrílicos
Ferroceno
UV-Vis
Voltametria
Oxadiazoles
Acrylic acids
Ferrocene
UV-Vis
Voltammetry
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Oxadiazoles
Acrylic acids
Ferrocene
UV-Vis
Voltammetry
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description A series of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles was synthesized through a one-pot condensation-cyclization reaction between 3-substituted acrylic acids and 5-aryl-1,2,4-oxadiazolyl-1,2,4-oxadiazoles, and were characterized through 1H NMR, 13C NMR, X-ray diffraction and HRMS. Products were obtained in rather variable yields (23 – 87 %). The cited compounds were compared to single heterocycle-containing (1,3,4-oxadiazole) examples in order to measure the influence of the 1,2,4-oxadiazole, as well as the substituents’, on the molecules. After a simple comparison of 1H NMR signs between cinnamic acid derivatives, two series of (E)-3-ferrocenylacrylic acid derivatives were characterized through UV-Vis spectroscopy and cyclic voltammetry. They were also tested for ct-DNA interaction, displaying strong interaction (K~106 M-1) with it. Finally, crotonic acid derivatives were reactive to the aminoacid cysteine, giving a series of adducts, which suggests a possible activity in future biological tests.
publishDate 2017
dc.date.issued.fl_str_mv 2017-02-24
dc.date.accessioned.fl_str_mv 2018-07-06T14:12:55Z
dc.date.available.fl_str_mv 2018-07-06T14:12:55Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/13682
url http://repositorio.ufsm.br/handle/1/13682
dc.language.iso.fl_str_mv por
language por
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dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química
dc.publisher.initials.fl_str_mv UFSM
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.source.none.fl_str_mv reponame:Manancial - Repositório Digital da UFSM
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