Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana

Detalhes bibliográficos
Ano de defesa: 2014
Autor(a) principal: Silva, Rafael Santos da lattes
Orientador(a): Rodrigues, Oscar Endrigo Dorneles lattes
Banca de defesa: Mostardeiro, Marco Aurelio lattes, Appelt, Helmoz Roseniaim 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:
Calcogenoésteres
Síntese verde
Atividade antibacteriana
Palavras-chave em Inglês:
Chalcogenoesters
Green synthesis
Antibacterial activity
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/17281
Resumo: The present work aims the synthesis of chalcogenoesters, by a green and versatile methodology, using low cost and non-toxic reagents, as well as the biological activity of this kind of compounds, as antibacterial agents. By a simple method, employing a small amount of solvent to the synthesis and separation, was performed the reaction between different acyl chlorides (1ae) and diorgaryl diselenides, in the presence of HCl/Zn0, using acetone as solvent, resulting in synthesis of 24 chalcogenoesters (compounds 2a-j, 3a-i e 4a-d), in moderate to excellent yields. The proposed synthesis showed to be high modular, allowing change a sort of different groups at specific molecule positions, besides the possibility to synthesize some examples of Sulfur and Selenium protecting groups (Fmoc and p-Nitrobenzoyl), compounds 4a, 2h, 3a, 3c, 3d, 4b and 3h, which the protocol was efficient. Furthermore, an investigation about the biological activity of the synthesized compounds was performed against Gram-Positive and Grandnegative bacteria strains of high clinical interest. Where the effectiveness of the chalcogenol esters, demonstrated against Klebsiella pneumoniae and Pseudomonas aeruginosa.
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spelling 2019-07-03T17:51:38Z2019-07-03T17:51:38Z2014-08-30http://repositorio.ufsm.br/handle/1/17281The present work aims the synthesis of chalcogenoesters, by a green and versatile methodology, using low cost and non-toxic reagents, as well as the biological activity of this kind of compounds, as antibacterial agents. By a simple method, employing a small amount of solvent to the synthesis and separation, was performed the reaction between different acyl chlorides (1ae) and diorgaryl diselenides, in the presence of HCl/Zn0, using acetone as solvent, resulting in synthesis of 24 chalcogenoesters (compounds 2a-j, 3a-i e 4a-d), in moderate to excellent yields. The proposed synthesis showed to be high modular, allowing change a sort of different groups at specific molecule positions, besides the possibility to synthesize some examples of Sulfur and Selenium protecting groups (Fmoc and p-Nitrobenzoyl), compounds 4a, 2h, 3a, 3c, 3d, 4b and 3h, which the protocol was efficient. Furthermore, an investigation about the biological activity of the synthesized compounds was performed against Gram-Positive and Grandnegative bacteria strains of high clinical interest. Where the effectiveness of the chalcogenol esters, demonstrated against Klebsiella pneumoniae and Pseudomonas aeruginosa.O presente trabalho tem por objetivo, a síntese de Tio-, Seleno- e Teluroésteres a partir de uma metodologia verde e versátil, empregando reagentes de baixo custo e toxicidade, além da avaliação do potencial biológico desta classe de compostos, como agentes antibacterianos. Através de uma metodologia simples utilizando um volume reduzido de solvente para as etapas de síntese e separação foi realizada a reação entre diferentes cloretos de ácidos (1a-e) e dicalcogenetos de diarila, na presença de Zn0/HCl, utilizando acetona como solvente levando a formação de 21 calcogenolésteres (compostos 2a-j, 3a-i e 4a-d) com rendimentos entre moderados à excelentes. A síntese proposta neste trabalho mostrou-se altamente modular, possibilitando variar diferentes grupos em posições específicas da molécula, além de permitir a síntese de exemplos envolvendo grupos protetores de Enxofre e Selênio, (Fmoc e p-nitrobenzoíla, compostos 4a, 2h, 3a, 3c, 3d, 4b e 3h), para os quais o protocolo desenvolvido foi eficiente. Por fim, foi realizado um estudo à cerca da atividade antibacteriana dos compostos sintetizados frente à bactérias Gram-positiva e Gram-negativa de alto interesse clínico, onde foi demonstrada a efetividade dos calcogenoésteres com relação à (Klebsiella pneumoniae e Pseudomonas aeruginosa) e (Staphylococcus aureus e Listeria monocytogenes).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/openAccessCalcogenoésteresSíntese verdeAtividade antibacterianaChalcogenoestersGreen synthesisAntibacterial activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacterianaVersatile and green synthesis of chalcogenol esters and antibacterial actitivity evaluationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisRodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980Appelt, Helmoz Roseniaimhttp://lattes.cnpq.br/5360357766246970http://lattes.cnpq.br/4522960269975592Silva, Rafael Santos da10060000000060009fef019-ac43-4d8b-83d3-3565e4686d7b5ff7e2fd-19fd-41e4-b59d-5129b85a61816190e59b-afb1-46bf-8172-0091c19640254684f279-563c-45a1-a01d-7d0ddd2378cbreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
dc.title.alternative.eng.fl_str_mv Versatile and green synthesis of chalcogenol esters and antibacterial actitivity evaluation
title Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
spellingShingle Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
Silva, Rafael Santos da
Calcogenoésteres
Síntese verde
Atividade antibacteriana
Chalcogenoesters
Green synthesis
Antibacterial activity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
title_full Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
title_fullStr Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
title_full_unstemmed Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
title_sort Síntese verde e versátil de calcogenol ésteres e avaliação da atividade antibacteriana
author Silva, Rafael Santos da
author_facet Silva, Rafael Santos da
author_role author
dc.contributor.advisor1.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/6536519955416085
dc.contributor.referee1.fl_str_mv Mostardeiro, Marco Aurelio
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/6195396264565980
dc.contributor.referee2.fl_str_mv Appelt, Helmoz Roseniaim
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/5360357766246970
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/4522960269975592
dc.contributor.author.fl_str_mv Silva, Rafael Santos da
contributor_str_mv Rodrigues, Oscar Endrigo Dorneles
Mostardeiro, Marco Aurelio
Appelt, Helmoz Roseniaim
dc.subject.por.fl_str_mv Calcogenoésteres
Síntese verde
Atividade antibacteriana
topic Calcogenoésteres
Síntese verde
Atividade antibacteriana
Chalcogenoesters
Green synthesis
Antibacterial activity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Chalcogenoesters
Green synthesis
Antibacterial activity
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description The present work aims the synthesis of chalcogenoesters, by a green and versatile methodology, using low cost and non-toxic reagents, as well as the biological activity of this kind of compounds, as antibacterial agents. By a simple method, employing a small amount of solvent to the synthesis and separation, was performed the reaction between different acyl chlorides (1ae) and diorgaryl diselenides, in the presence of HCl/Zn0, using acetone as solvent, resulting in synthesis of 24 chalcogenoesters (compounds 2a-j, 3a-i e 4a-d), in moderate to excellent yields. The proposed synthesis showed to be high modular, allowing change a sort of different groups at specific molecule positions, besides the possibility to synthesize some examples of Sulfur and Selenium protecting groups (Fmoc and p-Nitrobenzoyl), compounds 4a, 2h, 3a, 3c, 3d, 4b and 3h, which the protocol was efficient. Furthermore, an investigation about the biological activity of the synthesized compounds was performed against Gram-Positive and Grandnegative bacteria strains of high clinical interest. Where the effectiveness of the chalcogenol esters, demonstrated against Klebsiella pneumoniae and Pseudomonas aeruginosa.
publishDate 2014
dc.date.issued.fl_str_mv 2014-08-30
dc.date.accessioned.fl_str_mv 2019-07-03T17:51:38Z
dc.date.available.fl_str_mv 2019-07-03T17:51:38Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/17281
url http://repositorio.ufsm.br/handle/1/17281
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
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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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institution UFSM
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