4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas
Ano de defesa: | 2018 |
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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
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
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Departamento: |
Química
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País: |
Brasil
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Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/14794 |
Resumo: | In this thesis, methodologies were developed in order to obtain novel trifluormethyl substituted quinolines through intramolecular cyclocondensation reactions with subsequent C-C and C-N cross coupling of the Sonogashira, Buchwald-Hartwig and Ullmann type using phenylacetylene, morpholine, pyrrolidine and indole as precursors. Its electronic and structural properties were investigated by mass spectrometry, absorption and emission spectroscopy (photoluminescence), nuclear magnetic resonance of 1H and 13C, besides studies involving interaction with DNA and evaluation of possible antimicrobial properties. Initially, a series of 1-(1-((3-chloro-4-fluorophenyl)amino)-3,4-dihydronaphthalen-2-yl)-2,2,2-trifluoroethan-1-one (2a), (Z)-4-((3-chloro-4-fluorophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (2b-g) and (Z)-4-((4-bromophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3b-j) were obtained utilizing the precursors 3-chloro-4-fluoro-aniline, 4-bromo-aniline and 4-alkoxi-4-alkil[aryl(heteroaryl)]-1,1,1-trifluoro-3-alken-2-ones (1a-j) (R = CH3, C6H5, 4-FC6H4, 4-BrC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-furyl, 2-thienyl). Lastly, the enaminoketones compounds 2 and 3 were subjected to regiosselective intramolecular cyclization in sulfuric acid, resulting in 7-chloro-6-fluoro-4-(trifluoromethyl)quinolines (4) and 6-bromo-4-(trifluoromethyl)quinolines (5) in good yields (65 – 90%). Subsequently, C-C coupling reactions were performed in the quinolinic systems 4 and 5, where it was possible to obtain novel compounds 6-fluoro-7-(phenylethynyl)-4-(trifluoromethyl)quinolines (6) and 6-(phenylethynyl)-4-(trifluoromethyl)quinolines (7) in good yields (25 – 88%) through the Sonogashira coupling reaction using phenylacethylene as one of the precursors. Using the quinolines 5 together, as precursors, with the morpholine and pyrrolidine, it was possible to perform Buchwald-Hartwig coupling reactions, promoting the formation of new C-N bond. Thus, novel compounds 4-(4-(trifluoromethyl)quinolin-6-yl)morpholine (8) and 6-(pyrrolidin-1-yl)-4-(trifluoromethyl)quinolines (9) substituted with R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl were obtained in yields of 60 – 88%. Subsequently, the Ullmann coupling reaction catalyzed for CuI and DMEDA from the 6-bromo-quinolines (5) and indole, led in to obtaining a new series of five compounds 6-(1H-indol-1-yl)-4-(trifluoromethyl)quinolines (10) (R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl) with yields of 57 – 84%. The evaluation of photoluminescent properties of the quinolines 8 and 9 demonstrated that the compounds showed fuorescence in the region of blue for cyan, with moderated quantum yields in the 400 – 700 nm regions. In DNA interaction studies, the compounds showed strong ct-DNA bonding, especially the compounds substituted with morpholine at the 6-position of the quinolinic ring. The compounds 4-10 were evaluated against four types of bacterias and six types of fungi, but these were not active against the microorganism used. Further tests involving other types of bacterias and fungi should be performed to better evaluate the micro- and micobiologic properties of these novel 4-trifluoromethyl-quinolines. |
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oai:repositorio.ufsm.br:1/14794 |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2018-11-09T20:40:24Z2018-11-09T20:40:24Z2018-03-23http://repositorio.ufsm.br/handle/1/14794In this thesis, methodologies were developed in order to obtain novel trifluormethyl substituted quinolines through intramolecular cyclocondensation reactions with subsequent C-C and C-N cross coupling of the Sonogashira, Buchwald-Hartwig and Ullmann type using phenylacetylene, morpholine, pyrrolidine and indole as precursors. Its electronic and structural properties were investigated by mass spectrometry, absorption and emission spectroscopy (photoluminescence), nuclear magnetic resonance of 1H and 13C, besides studies involving interaction with DNA and evaluation of possible antimicrobial properties. Initially, a series of 1-(1-((3-chloro-4-fluorophenyl)amino)-3,4-dihydronaphthalen-2-yl)-2,2,2-trifluoroethan-1-one (2a), (Z)-4-((3-chloro-4-fluorophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (2b-g) and (Z)-4-((4-bromophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3b-j) were obtained utilizing the precursors 3-chloro-4-fluoro-aniline, 4-bromo-aniline and 4-alkoxi-4-alkil[aryl(heteroaryl)]-1,1,1-trifluoro-3-alken-2-ones (1a-j) (R = CH3, C6H5, 4-FC6H4, 4-BrC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-furyl, 2-thienyl). Lastly, the enaminoketones compounds 2 and 3 were subjected to regiosselective intramolecular cyclization in sulfuric acid, resulting in 7-chloro-6-fluoro-4-(trifluoromethyl)quinolines (4) and 6-bromo-4-(trifluoromethyl)quinolines (5) in good yields (65 – 90%). Subsequently, C-C coupling reactions were performed in the quinolinic systems 4 and 5, where it was possible to obtain novel compounds 6-fluoro-7-(phenylethynyl)-4-(trifluoromethyl)quinolines (6) and 6-(phenylethynyl)-4-(trifluoromethyl)quinolines (7) in good yields (25 – 88%) through the Sonogashira coupling reaction using phenylacethylene as one of the precursors. Using the quinolines 5 together, as precursors, with the morpholine and pyrrolidine, it was possible to perform Buchwald-Hartwig coupling reactions, promoting the formation of new C-N bond. Thus, novel compounds 4-(4-(trifluoromethyl)quinolin-6-yl)morpholine (8) and 6-(pyrrolidin-1-yl)-4-(trifluoromethyl)quinolines (9) substituted with R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl were obtained in yields of 60 – 88%. Subsequently, the Ullmann coupling reaction catalyzed for CuI and DMEDA from the 6-bromo-quinolines (5) and indole, led in to obtaining a new series of five compounds 6-(1H-indol-1-yl)-4-(trifluoromethyl)quinolines (10) (R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl) with yields of 57 – 84%. The evaluation of photoluminescent properties of the quinolines 8 and 9 demonstrated that the compounds showed fuorescence in the region of blue for cyan, with moderated quantum yields in the 400 – 700 nm regions. In DNA interaction studies, the compounds showed strong ct-DNA bonding, especially the compounds substituted with morpholine at the 6-position of the quinolinic ring. The compounds 4-10 were evaluated against four types of bacterias and six types of fungi, but these were not active against the microorganism used. Further tests involving other types of bacterias and fungi should be performed to better evaluate the micro- and micobiologic properties of these novel 4-trifluoromethyl-quinolines.Nesta tese foram desenvolvidas metodologias para a obtenção de novas quinolinas trifluormetil substituídas através de reações de ciclocondensação intramoleculares com posteriores acoplamentos cruzados C-C e C-N do tipo Sonogashira, Buchwald-Hartwig e Ullmann utilizando fenilacetileno, morfolina, pirrolidina e indol como precursores. Suas propriedades estruturais e eletrônicas foram investigadas por espectrometria de massas, espectroscopia eletrônica de absorção e emissão (fotoluminescência), ressonância magnética nuclear de 1H e 13C, além de estudos envolvendo interação com o DNA e avaliação de possíveis propriedades antimicrobianas. Inicialmente foram obtidas uma série de 1-(1-((3-cloro-4-fluorfenil)amino)-3,4-diidronaftalen-2-il)-2,2,2-trifluoretan-1-ona (2a), (Z)-4-((3-cloro-4-fluorfenil)amino)-1,1,1-triflúor-3-alquen-2-onas (2b-g) e (Z)-4-((4-bromofenil)amino)-1,1,1-triflúor-3-alquen-2-onas (3b-j) utilizando os precursores 3-cloro-4-flúor-anilina, 4-bromo-anilina e 4-alcóxi-4-alquila[arila(heteroarila)]-1,1,1-triflúor-3-alquen-2-onas (1a-j) (R = CH3, C6H5, 4-FC6H4, 4-BrC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-furila, 2-tienila). Após, os compostos enamino cetônicos 2 e 3 foram submetidos à reação regiosseletiva de ciclização intramolecular em ácido sulfúrico, resultando em 7-cloro-6-flúor-4-(trifluormetil)quinolinas (4) e 6-bromo-4-(trifluormetil)quinolinas (5) com bons rendimentos (65 – 90%). Posteriormente, reações de acoplamento C-C foram realizadas nos sistemas quinolínicos 4 e 5, sendo possível obter sistemas inéditos 6-flúor-7-(feniletinil)-4-(trifluormetil)quinolinas (6) e 6-(feniletinil)-4-(trifluormetil)quinolinas (7) com bons rendimentos (25 – 88%) através da reação de acoplamento de Sonogashira utilizando fenilacetileno como um dos precursores. Utilizando como precursores as quinolinas 5 juntamente com as aminas morfolina e pirrolidina, foi possível realizar reações de acoplamento de Buchwald-Hartwig, promovendo a formação de novas ligações C-N. Desta forma, novos compostos 4-(4-(trifluormetil)quinolin-6-il)morfolina (8) e 6-(pirrolidin-1-il)-4-(trifluormetil)quinolinas (9) substituídos com R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-tienila foram obtidos com rendimentos de 60 – 88%. Em sequência, as reações de acoplamento de Ullmann catalisadas por CuI e DMEDA a partir das 6-bromo-quinolinas (5) e indol, conduziram à obtenção de uma série inédita de cinco compostos 6-(1H-indol-1-il)-4-(trifluormetil)quinolinas (10) (R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-tienila) com rendimentos de 57 – 84%. A avaliação das propriedades fotoluminescentes das quinolinas 8 e 9 demonstrou que os compostos apresentaram fluorescência na região do azul para ciano, com moderados rendimentos quânticos na região de 400 – 700 nm. Nos estudos de interação com o DNA, os compostos apresentaram ligação com ct-DNA, principalmente os compostos substituídos com morfolina na posição 6 do anel quinolínico. Os compostos 4-10 foram avaliados frente a quatro tipos de bactérias e seis tipos de leveduras, mas estes não se mostraram ativos frente aos microrganismos utilizados. Mais testes envolvendo outros tipos de bactérias e leveduras devem ser realizados para melhor avaliar as propriedades micro- e micobiológicas destas novas 4-trifluormetil-quinolinas.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccess4-(trifluormetil)haloquinolinasReações de acoplamento C-C e C-NPropriedades fotoluminescentes4-(trifluoromethyl)haloquinolinesC-C and C-N coupling reactionsPhotoluminescent propertiesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas4-(trifluoromethyl)haloquinolines: synthesis, C-C and C-N cross coupling reactions, photoluminescent and antimicrobial propertiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Andrighetto, Rosáliahttp://lattes.cnpq.br/9569995843681336Merlo, Aloir Antoniohttp://lattes.cnpq.br/7385210507816401http://lattes.cnpq.br/5087148127700008Rodrigues, Melissa Budke10060000000060006c852ad-d805-43c3-99d6-93a6a86f507c5df7652d-b999-4213-87dc-27512204d0fc483d6d0c-e419-454b-b413-1a51673258c32f7bd6ce-78fa-4968-ac66-2d1407e90f60909c149e-f66a-45b5-8b3f-23d55fb2727b72a494d1-5ae2-4845-8074-1d6ada9050e0reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdfTES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdfTese de Doutoradoapplication/pdf35847470http://repositorio.ufsm.br/bitstream/1/14794/1/TES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdfc046793acf307ec2439dee4b73418ddbMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
dc.title.alternative.eng.fl_str_mv |
4-(trifluoromethyl)haloquinolines: synthesis, C-C and C-N cross coupling reactions, photoluminescent and antimicrobial properties |
title |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
spellingShingle |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas Rodrigues, Melissa Budke 4-(trifluormetil)haloquinolinas Reações de acoplamento C-C e C-N Propriedades fotoluminescentes 4-(trifluoromethyl)haloquinolines C-C and C-N coupling reactions Photoluminescent properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
title_full |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
title_fullStr |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
title_full_unstemmed |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
title_sort |
4-(trifluormetil)haloquinolinas: síntese, reações de acoplamento cruzado C-C e C-N, propriedades fotoluminescentes e antimicrobianas |
author |
Rodrigues, Melissa Budke |
author_facet |
Rodrigues, Melissa Budke |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee3.fl_str_mv |
Andrighetto, Rosália |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/9569995843681336 |
dc.contributor.referee4.fl_str_mv |
Merlo, Aloir Antonio |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/7385210507816401 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5087148127700008 |
dc.contributor.author.fl_str_mv |
Rodrigues, Melissa Budke |
contributor_str_mv |
Bonacorso, Helio Gauze Iglesias, Bernardo Almeida Zanatta, Nilo Andrighetto, Rosália Merlo, Aloir Antonio |
dc.subject.por.fl_str_mv |
4-(trifluormetil)haloquinolinas Reações de acoplamento C-C e C-N Propriedades fotoluminescentes |
topic |
4-(trifluormetil)haloquinolinas Reações de acoplamento C-C e C-N Propriedades fotoluminescentes 4-(trifluoromethyl)haloquinolines C-C and C-N coupling reactions Photoluminescent properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
4-(trifluoromethyl)haloquinolines C-C and C-N coupling reactions Photoluminescent properties |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this thesis, methodologies were developed in order to obtain novel trifluormethyl substituted quinolines through intramolecular cyclocondensation reactions with subsequent C-C and C-N cross coupling of the Sonogashira, Buchwald-Hartwig and Ullmann type using phenylacetylene, morpholine, pyrrolidine and indole as precursors. Its electronic and structural properties were investigated by mass spectrometry, absorption and emission spectroscopy (photoluminescence), nuclear magnetic resonance of 1H and 13C, besides studies involving interaction with DNA and evaluation of possible antimicrobial properties. Initially, a series of 1-(1-((3-chloro-4-fluorophenyl)amino)-3,4-dihydronaphthalen-2-yl)-2,2,2-trifluoroethan-1-one (2a), (Z)-4-((3-chloro-4-fluorophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (2b-g) and (Z)-4-((4-bromophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3b-j) were obtained utilizing the precursors 3-chloro-4-fluoro-aniline, 4-bromo-aniline and 4-alkoxi-4-alkil[aryl(heteroaryl)]-1,1,1-trifluoro-3-alken-2-ones (1a-j) (R = CH3, C6H5, 4-FC6H4, 4-BrC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-furyl, 2-thienyl). Lastly, the enaminoketones compounds 2 and 3 were subjected to regiosselective intramolecular cyclization in sulfuric acid, resulting in 7-chloro-6-fluoro-4-(trifluoromethyl)quinolines (4) and 6-bromo-4-(trifluoromethyl)quinolines (5) in good yields (65 – 90%). Subsequently, C-C coupling reactions were performed in the quinolinic systems 4 and 5, where it was possible to obtain novel compounds 6-fluoro-7-(phenylethynyl)-4-(trifluoromethyl)quinolines (6) and 6-(phenylethynyl)-4-(trifluoromethyl)quinolines (7) in good yields (25 – 88%) through the Sonogashira coupling reaction using phenylacethylene as one of the precursors. Using the quinolines 5 together, as precursors, with the morpholine and pyrrolidine, it was possible to perform Buchwald-Hartwig coupling reactions, promoting the formation of new C-N bond. Thus, novel compounds 4-(4-(trifluoromethyl)quinolin-6-yl)morpholine (8) and 6-(pyrrolidin-1-yl)-4-(trifluoromethyl)quinolines (9) substituted with R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl were obtained in yields of 60 – 88%. Subsequently, the Ullmann coupling reaction catalyzed for CuI and DMEDA from the 6-bromo-quinolines (5) and indole, led in to obtaining a new series of five compounds 6-(1H-indol-1-yl)-4-(trifluoromethyl)quinolines (10) (R = C6H5, 4-FC6H4, 4-CH3C6H4, 4-CF3C6H4, 2-thienyl) with yields of 57 – 84%. The evaluation of photoluminescent properties of the quinolines 8 and 9 demonstrated that the compounds showed fuorescence in the region of blue for cyan, with moderated quantum yields in the 400 – 700 nm regions. In DNA interaction studies, the compounds showed strong ct-DNA bonding, especially the compounds substituted with morpholine at the 6-position of the quinolinic ring. The compounds 4-10 were evaluated against four types of bacterias and six types of fungi, but these were not active against the microorganism used. Further tests involving other types of bacterias and fungi should be performed to better evaluate the micro- and micobiologic properties of these novel 4-trifluoromethyl-quinolines. |
publishDate |
2018 |
dc.date.accessioned.fl_str_mv |
2018-11-09T20:40:24Z |
dc.date.available.fl_str_mv |
2018-11-09T20:40:24Z |
dc.date.issued.fl_str_mv |
2018-03-23 |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/14794 |
url |
http://repositorio.ufsm.br/handle/1/14794 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
06c852ad-d805-43c3-99d6-93a6a86f507c 5df7652d-b999-4213-87dc-27512204d0fc 483d6d0c-e419-454b-b413-1a51673258c3 2f7bd6ce-78fa-4968-ac66-2d1407e90f60 909c149e-f66a-45b5-8b3f-23d55fb2727b 72a494d1-5ae2-4845-8074-1d6ada9050e0 |
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:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/14794/1/TES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdf http://repositorio.ufsm.br/bitstream/1/14794/2/license_rdf http://repositorio.ufsm.br/bitstream/1/14794/3/license.txt http://repositorio.ufsm.br/bitstream/1/14794/4/TES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdf.txt http://repositorio.ufsm.br/bitstream/1/14794/5/TES_PPGQUIMICA_2018_RODRIGUES_MELISSA.pdf.jpg |
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repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793240155814887424 |