Síntese derivados fenilpropanóicos

Detalhes bibliográficos
Autor(a) principal: Borges, Flávio Valadares Pereira
Data de Publicação: 2020
Tipo de documento: Tese
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações da UFPB
Texto Completo: https://repositorio.ufpb.br/jspui/handle/123456789/18718
Resumo: Phenylpropanoids and their derivatives have been widely studied for their structural varieties and biological activities. This work reports the obtaining of esters of phenylpropanoic acids and monoterpenic alcohols, obtained through the reactions of Schotten-Bauman and WittigHorner, the obtaining of the neolignan dehydrodieugenol by oxidative coupling promoted by potassium ferrocyanide and peroxidase contained in coconut water, as well as the report of its leishimanicidal activities for the promastigote form of Leishmania amazonensis and the comparison between the techniques regarding stereo selectivity. The neolignan lycarin- (A) was obtained, with the coupling promoted by coconut water and variations were made in the order of addition of reagents and injection speed comparing the influence on yield, methyl lignan dehydrodicumarate was also synthesized, obtained through esterification Fischer and subsequent oxidative coupling. Four phenylethylamines and two indoletylamines cinamoylamides were also obtained, these being described for the first time in this work through the formation of acyl chloride with Vilsmeyer-Haack reagent and later SchottenBaumann reaction to form amide. The results of this work yielded three publications in pharmaceutical chemistry journals.
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spelling Síntese derivados fenilpropanóicosLignanasNeolignanasReagente de Vilsmeyer-HaackCinamoilamidasCNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIAPhenylpropanoids and their derivatives have been widely studied for their structural varieties and biological activities. This work reports the obtaining of esters of phenylpropanoic acids and monoterpenic alcohols, obtained through the reactions of Schotten-Bauman and WittigHorner, the obtaining of the neolignan dehydrodieugenol by oxidative coupling promoted by potassium ferrocyanide and peroxidase contained in coconut water, as well as the report of its leishimanicidal activities for the promastigote form of Leishmania amazonensis and the comparison between the techniques regarding stereo selectivity. The neolignan lycarin- (A) was obtained, with the coupling promoted by coconut water and variations were made in the order of addition of reagents and injection speed comparing the influence on yield, methyl lignan dehydrodicumarate was also synthesized, obtained through esterification Fischer and subsequent oxidative coupling. Four phenylethylamines and two indoletylamines cinamoylamides were also obtained, these being described for the first time in this work through the formation of acyl chloride with Vilsmeyer-Haack reagent and later SchottenBaumann reaction to form amide. The results of this work yielded three publications in pharmaceutical chemistry journals.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFenilpropanóides e seus derivados vem sendo amplamente estudados pelas suas variedades estruturais e atividades biológicas. Neste trabalho são relatadas a obtenção de ésteres de ácidos fenilpropanoicos e álcoois monoterpênicos, obtidos através das reações de Schotten-Bauman e Wittig-Horner, a obtenção da neolignana dehidrodieugenol por acoplamento oxidativo promovido pelo ferrocianeto de potássio e pela peróxidase contida na agua de coco, assim como o relato de suas atividades leishimanicida para a forma promastigota da Leishmania amazonensis e a comparação entre as técnicas quanto a estéreo seletividade. Foram obtidas a neolignana licarina-(A), com o acoplamento promovido pela água de coco e feitas variações na ordem de adição dos reagentes e velocidade de injeção comparando a influência no rendimento, também foi sintetizada a lignana dehidrodicumarato de metila, obtida através de esterificação de Fischer e posterior acoplamento oxidativo. Também foram obtidas quatro cinamoilamidas de feniletilaminas e duas de indoletilaminas, estas, sendo descritas pela primeira vez neste trabalho através da formação do cloreto de acila com reagente de Vilsmeyer-Haack e posterior reação de Schotten-Baumann para formação da amida. Os resultados desse trabalho renderam três publicações em periódicos de farmacoquímica.Universidade Federal da ParaíbaBrasilFarmacologiaPrograma de Pós-Graduação em Produtos Naturais e Sintéticos BioativosUFPBBarbosa Filho, José Mariahttp://lattes.cnpq.br/8892459126928726Rodrigues, Luis Cézarhttp://lattes.cnpq.br/0211744581268049Borges, Flávio Valadares Pereira2020-12-13T19:54:36Z2021-03-312020-12-13T19:54:36Z2020-03-31info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesishttps://repositorio.ufpb.br/jspui/handle/123456789/18718porhttp://creativecommons.org/licenses/by-nd/3.0/br/info:eu-repo/semantics/embargoedAccessreponame:Biblioteca Digital de Teses e Dissertações da UFPBinstname:Universidade Federal da Paraíba (UFPB)instacron:UFPB2021-09-02T23:33:37Zoai:repositorio.ufpb.br:123456789/18718Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2021-09-02T23:33:37Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false
dc.title.none.fl_str_mv Síntese derivados fenilpropanóicos
title Síntese derivados fenilpropanóicos
spellingShingle Síntese derivados fenilpropanóicos
Borges, Flávio Valadares Pereira
Lignanas
Neolignanas
Reagente de Vilsmeyer-Haack
Cinamoilamidas
CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA
title_short Síntese derivados fenilpropanóicos
title_full Síntese derivados fenilpropanóicos
title_fullStr Síntese derivados fenilpropanóicos
title_full_unstemmed Síntese derivados fenilpropanóicos
title_sort Síntese derivados fenilpropanóicos
author Borges, Flávio Valadares Pereira
author_facet Borges, Flávio Valadares Pereira
author_role author
dc.contributor.none.fl_str_mv Barbosa Filho, José Maria
http://lattes.cnpq.br/8892459126928726
Rodrigues, Luis Cézar
http://lattes.cnpq.br/0211744581268049
dc.contributor.author.fl_str_mv Borges, Flávio Valadares Pereira
dc.subject.por.fl_str_mv Lignanas
Neolignanas
Reagente de Vilsmeyer-Haack
Cinamoilamidas
CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA
topic Lignanas
Neolignanas
Reagente de Vilsmeyer-Haack
Cinamoilamidas
CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA
description Phenylpropanoids and their derivatives have been widely studied for their structural varieties and biological activities. This work reports the obtaining of esters of phenylpropanoic acids and monoterpenic alcohols, obtained through the reactions of Schotten-Bauman and WittigHorner, the obtaining of the neolignan dehydrodieugenol by oxidative coupling promoted by potassium ferrocyanide and peroxidase contained in coconut water, as well as the report of its leishimanicidal activities for the promastigote form of Leishmania amazonensis and the comparison between the techniques regarding stereo selectivity. The neolignan lycarin- (A) was obtained, with the coupling promoted by coconut water and variations were made in the order of addition of reagents and injection speed comparing the influence on yield, methyl lignan dehydrodicumarate was also synthesized, obtained through esterification Fischer and subsequent oxidative coupling. Four phenylethylamines and two indoletylamines cinamoylamides were also obtained, these being described for the first time in this work through the formation of acyl chloride with Vilsmeyer-Haack reagent and later SchottenBaumann reaction to form amide. The results of this work yielded three publications in pharmaceutical chemistry journals.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-13T19:54:36Z
2020-12-13T19:54:36Z
2020-03-31
2021-03-31
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 https://repositorio.ufpb.br/jspui/handle/123456789/18718
url https://repositorio.ufpb.br/jspui/handle/123456789/18718
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv http://creativecommons.org/licenses/by-nd/3.0/br/
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nd/3.0/br/
eu_rights_str_mv embargoedAccess
dc.publisher.none.fl_str_mv Universidade Federal da Paraíba
Brasil
Farmacologia
Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos
UFPB
publisher.none.fl_str_mv Universidade Federal da Paraíba
Brasil
Farmacologia
Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos
UFPB
dc.source.none.fl_str_mv reponame:Biblioteca Digital de Teses e Dissertações da UFPB
instname:Universidade Federal da Paraíba (UFPB)
instacron:UFPB
instname_str Universidade Federal da Paraíba (UFPB)
instacron_str UFPB
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reponame_str Biblioteca Digital de Teses e Dissertações da UFPB
collection Biblioteca Digital de Teses e Dissertações da UFPB
repository.name.fl_str_mv Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)
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