SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFMS |
Texto Completo: | https://repositorio.ufms.br/handle/123456789/3640 |
Resumo: | Selenium-containing naphthoquinones are biologically relevant hybrid structure and can be used for diverse biological activities. In this thesis we planned to synthesize a series of new selenium-functionalized naphthoquinone derivatives, from the reaction of (E)-2-(dec-1-en-3-yl)-3-hydroxynaphthalene-1,4-dione and structurally diverse diorganoyl diselenides, by utilizing I2/DMSO catalytic oxidant system. By using our methodology, six new selenylated products were obtained and their structures were confirmed by using spectroscopic and spectrometric techniques. Structural factors influenced the electrophilic properties of quinonoid molecules, forming mainly o-quinones compounds, such as the compound 2-heptyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo [h] chromene-5,6-dione. Starting from p-methoxy diphenyl diselenide, o- and p-naphthoquinone derivatives were obtained. In general, the reactions resulted in the selenylated products in low yields. However, due to the interesting feature of this hybrid structure, we extended our studies to other substituted diselenides, and it was possible to obtain a series of new compounds with biological and pharmaceutical interest. |
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2021-04-28T14:07:14Z2021-09-30T19:55:50Z2021https://repositorio.ufms.br/handle/123456789/3640Selenium-containing naphthoquinones are biologically relevant hybrid structure and can be used for diverse biological activities. In this thesis we planned to synthesize a series of new selenium-functionalized naphthoquinone derivatives, from the reaction of (E)-2-(dec-1-en-3-yl)-3-hydroxynaphthalene-1,4-dione and structurally diverse diorganoyl diselenides, by utilizing I2/DMSO catalytic oxidant system. By using our methodology, six new selenylated products were obtained and their structures were confirmed by using spectroscopic and spectrometric techniques. Structural factors influenced the electrophilic properties of quinonoid molecules, forming mainly o-quinones compounds, such as the compound 2-heptyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo [h] chromene-5,6-dione. Starting from p-methoxy diphenyl diselenide, o- and p-naphthoquinone derivatives were obtained. In general, the reactions resulted in the selenylated products in low yields. However, due to the interesting feature of this hybrid structure, we extended our studies to other substituted diselenides, and it was possible to obtain a series of new compounds with biological and pharmaceutical interest.Naftoquinonas contendo grupamentos organosselênio constituem importantes substâncias para diversos alvos biológicos. Planejou-se a síntese de uma série de novos derivados naftoquinônicos heterocíclicos selenofuncionalizados, por meio de reações entre o composto (E)-2-(Dec-2-enil)-3-hidroxinaftaleno-1,4-diona e diferentes disselenetos de diorganoíla via sistema catalítico I2/DMSO. Foram obtidos seis novos compostos, que tiveram suas estruturas confirmadas por meio de técnicas espectroscópicas e espectrométricas. Fatores estruturais podem influenciar nas propriedades eletrofílicas das moléculas quinonoídicas formando principalmente compostos o-quinônicos, como por exemplo o composto 2-heptil-3-(fenilseleno)-3,4-diidro-2H-benzo[h] cromeno-5,6-diona. Partindo do disseleneto de p-metoxi difenila, foram obtidos os derivados o- e p-naftoquinônicos. De modo geral, as reações resultaram em baixos rendimentos. Contudo, a execução deste planejamento sintético possibilitou a obtenção de novos compostos de interesse farmacêutico.Fundação Universidade Federal de Mato Grosso do SulUFMSBrasilLapacholLapachonasCiclizaçãoCalcogênioNucleófiloSÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICOinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisDenis Pires de LimaAline Alves dos Santos Naujorksinfo:eu-repo/semantics/openAccessporreponame:Repositório Institucional da UFMSinstname:Universidade Federal de Mato Grosso do Sul (UFMS)instacron:UFMSTHUMBNAILTese_AlineNaujorks_versãofinal.pdf.jpgTese_AlineNaujorks_versãofinal.pdf.jpgGenerated Thumbnailimage/jpeg1285https://repositorio.ufms.br/bitstream/123456789/3640/3/Tese_AlineNaujorks_vers%c3%a3ofinal.pdf.jpg38b9a445e5a549393dbeccf333b3ba27MD53TEXTTese_AlineNaujorks_versãofinal.pdf.txtTese_AlineNaujorks_versãofinal.pdf.txtExtracted texttext/plain160889https://repositorio.ufms.br/bitstream/123456789/3640/2/Tese_AlineNaujorks_vers%c3%a3ofinal.pdf.txtad80d42d7fb86ed18665c7f1b710ee6bMD52ORIGINALTese_AlineNaujorks_versãofinal.pdfTese_AlineNaujorks_versãofinal.pdfapplication/pdf3696620https://repositorio.ufms.br/bitstream/123456789/3640/1/Tese_AlineNaujorks_vers%c3%a3ofinal.pdf13f9cf78c1abe106d681670d8f26bf59MD51123456789/36402021-09-30 15:55:50.58oai:repositorio.ufms.br:123456789/3640Repositório InstitucionalPUBhttps://repositorio.ufms.br/oai/requestri.prograd@ufms.bropendoar:21242021-09-30T19:55:50Repositório Institucional da UFMS - Universidade Federal de Mato Grosso do Sul (UFMS)false |
dc.title.pt_BR.fl_str_mv |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
title |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
spellingShingle |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO Aline Alves dos Santos Naujorks Lapachol Lapachonas Ciclização Calcogênio Nucleófilo |
title_short |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
title_full |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
title_fullStr |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
title_full_unstemmed |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
title_sort |
SÍNTESE DE NAFTOQUINONAS HETEROCÍCLICAS SELENOFUNCIONALIZADAS DE INTERESSE FARMACÊUTICO |
author |
Aline Alves dos Santos Naujorks |
author_facet |
Aline Alves dos Santos Naujorks |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Denis Pires de Lima |
dc.contributor.author.fl_str_mv |
Aline Alves dos Santos Naujorks |
contributor_str_mv |
Denis Pires de Lima |
dc.subject.por.fl_str_mv |
Lapachol Lapachonas Ciclização Calcogênio Nucleófilo |
topic |
Lapachol Lapachonas Ciclização Calcogênio Nucleófilo |
description |
Selenium-containing naphthoquinones are biologically relevant hybrid structure and can be used for diverse biological activities. In this thesis we planned to synthesize a series of new selenium-functionalized naphthoquinone derivatives, from the reaction of (E)-2-(dec-1-en-3-yl)-3-hydroxynaphthalene-1,4-dione and structurally diverse diorganoyl diselenides, by utilizing I2/DMSO catalytic oxidant system. By using our methodology, six new selenylated products were obtained and their structures were confirmed by using spectroscopic and spectrometric techniques. Structural factors influenced the electrophilic properties of quinonoid molecules, forming mainly o-quinones compounds, such as the compound 2-heptyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo [h] chromene-5,6-dione. Starting from p-methoxy diphenyl diselenide, o- and p-naphthoquinone derivatives were obtained. In general, the reactions resulted in the selenylated products in low yields. However, due to the interesting feature of this hybrid structure, we extended our studies to other substituted diselenides, and it was possible to obtain a series of new compounds with biological and pharmaceutical interest. |
publishDate |
2021 |
dc.date.accessioned.fl_str_mv |
2021-04-28T14:07:14Z |
dc.date.available.fl_str_mv |
2021-09-30T19:55:50Z |
dc.date.issued.fl_str_mv |
2021 |
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.ufms.br/handle/123456789/3640 |
url |
https://repositorio.ufms.br/handle/123456789/3640 |
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por |
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por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
dc.publisher.none.fl_str_mv |
Fundação Universidade Federal de Mato Grosso do Sul |
dc.publisher.initials.fl_str_mv |
UFMS |
dc.publisher.country.fl_str_mv |
Brasil |
publisher.none.fl_str_mv |
Fundação Universidade Federal de Mato Grosso do Sul |
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reponame:Repositório Institucional da UFMS instname:Universidade Federal de Mato Grosso do Sul (UFMS) instacron:UFMS |
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