Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
Texto Completo: | https://tede.ufrrj.br/jspui/handle/tede/25 |
Resumo: | This work involved the study of the 1,3,4-thiadiazolium-2-amine mesoionic compounds class rearrangement, in the corresponding 1,3,4-triazolium-2-thiolate and the chemo-biological properties evaluation, such as antioxidant and antitirosinase activities. The mesoionic compounds generally possess structures which allow new heterocycles synthesis, and also interactions with biomolecules, such as DNA and proteins, which are important factors to explain their different biological activities. The mesoionic compounds studied in this work were the 1,3,4-triazolium-2-thiolate class obtained by the molecular rearrangement of their 1,3,4-thiadiazole-2-amine isomers in the presence of the nucleophilic solvents, under reflux and microwave irradiation. The 1,2,3- oxadiazolium-5-olate (sydnones) class were further synthesized. Mesoionic derivatives of the 1,3,4-thiadiazolium-2-aminide class, in hydrochloride form as well as a free base, and the 1,2,3-oxadiazolium-5-olate class were obtained by classical reactions already described in the literature. The use of microwave irradiation, in the presence of solid support and the Lewis acid, provided the mesoionic compounds 1,3,4-triazolium-2-tiolate in unprecedented quantitative yields, and much smaller reaction times (3 minutes) when compared to traditional methods (8 hours). Therefore, it presented high efficiency in molecular rearrangement. All synthesized mesoionic compounds were characterized by spectroscopic techniques, such as IR, UV, 1H and 13C NMR. The antioxidant activity evaluation of the mesoionic compounds showed to be promising for the 1,3,4-triazolium-2-thiolate and 1,3,4-thiadiazole-2-amine classes, especially in the hydrochloride form. The evaluation of the tyrosinase enzyme inhibition was performed to all synthesized compounds, but a higher activity was noticed in the 1,2,3-oxadiazole-5-olate class derivatives results. |
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Lima, Aurea Echevarria Aznar Neves668.742.388-68http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787205D1109.818.207-35http://lattes.cnpq.br/3300847150379345Canuto, Andr? Vinicius dos Santos2016-04-26T13:52:03Z2009-08-102009-04-07CANUTO, Andr? Vinicius dos Santos. Compostos Mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase. 2009. 174 f. Disserta??o (Mestrado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009.https://tede.ufrrj.br/jspui/handle/tede/25This work involved the study of the 1,3,4-thiadiazolium-2-amine mesoionic compounds class rearrangement, in the corresponding 1,3,4-triazolium-2-thiolate and the chemo-biological properties evaluation, such as antioxidant and antitirosinase activities. The mesoionic compounds generally possess structures which allow new heterocycles synthesis, and also interactions with biomolecules, such as DNA and proteins, which are important factors to explain their different biological activities. The mesoionic compounds studied in this work were the 1,3,4-triazolium-2-thiolate class obtained by the molecular rearrangement of their 1,3,4-thiadiazole-2-amine isomers in the presence of the nucleophilic solvents, under reflux and microwave irradiation. The 1,2,3- oxadiazolium-5-olate (sydnones) class were further synthesized. Mesoionic derivatives of the 1,3,4-thiadiazolium-2-aminide class, in hydrochloride form as well as a free base, and the 1,2,3-oxadiazolium-5-olate class were obtained by classical reactions already described in the literature. The use of microwave irradiation, in the presence of solid support and the Lewis acid, provided the mesoionic compounds 1,3,4-triazolium-2-tiolate in unprecedented quantitative yields, and much smaller reaction times (3 minutes) when compared to traditional methods (8 hours). Therefore, it presented high efficiency in molecular rearrangement. All synthesized mesoionic compounds were characterized by spectroscopic techniques, such as IR, UV, 1H and 13C NMR. The antioxidant activity evaluation of the mesoionic compounds showed to be promising for the 1,3,4-triazolium-2-thiolate and 1,3,4-thiadiazole-2-amine classes, especially in the hydrochloride form. The evaluation of the tyrosinase enzyme inhibition was performed to all synthesized compounds, but a higher activity was noticed in the 1,2,3-oxadiazole-5-olate class derivatives results.Este trabalho envolveu o estudo do rearranjo de compostos mesoi?nicos da classe 1,3,4-tiadiaz?lio-2-aminida nos correspondentes 1,3,4-triaz?lio-2-tiolato e suas propriedades quimio-biol?gicas, tais como atividade antioxidante e antitirosinase. Os mesoi?nicos de forma geral apresentam estruturas que possibilitam a s?ntese de novas subst?ncias heteroc?clicas, al?m de intera??es com biomol?culas, tais como o DNA e prote?nas, fatores importantes que contribuem para explicar suas variadas atividades biol?gicas. Os compostos mesoi?nicos estudados nesta disserta??o foram os derivados da classe 1,3,4-triaz?lio-2-tiolato obtidos atrav?s do rearranjo molecular de seus is?meros 1,3,4- tiadiaz?lio-2-aminida na presen?a de solventes nucleof?licos a refluxo e sob irradia??o de microondas, e os da classe 1,2,3-oxadiazol-5-olato (sidnonas). Os derivados mesoi?nicos das classes 1,3,4-tiadiaz?lio-2-aminida, tanto na forma de cloridrato como a de base livre, e os da classe 1,2,3-oxadiazol-5-olato foram obtidos atrav?s de rea??es cl?ssicas j? descritas na literatura. O uso da irradia??o de microondas na presen?a de suporte s?lido e ?cido de Lewis proporcionou a s?ntese dos mesoi?nicos, 1,3,4-triaz?lio-2-tiolato, de forma in?dita, em rendimentos quantitativos e em tempos de rea??o muito menores (3 minutos) quando comparados os da metodologia tradicional (8 horas) apresentando, portanto, grande efici?ncia no rearranjo molecular. Todos os compostos mesoi?nicos obtidos foram caracterizados por t?cnicas espectrosc?picas, como Infravermelho, UV, RMN 1H e 13C. A avalia??o da atividade antioxidante dos compostos mesoi?nicos mostrou-se promissora para os derivados da classe 1,3,4-triaz?lio-2-tiolato e para os da classe 1,3,4- tiadiaz?lio-2-aminida, especialmente na forma de cloridratos. A avalia??o da atividade de inibi??o frente ? enzima tirosinase foi realizada para todos os compostos sintetizados e os resultados mostraram maior atividade para os derivados da classe 1,2,3-oxadiazol-5-olato.Made available in DSpace on 2016-04-26T13:52:03Z (GMT). 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dc.title.por.fl_str_mv |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
title |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
spellingShingle |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase Canuto, Andr? Vinicius dos Santos compostos mesoi?nicos rearranjo molecular 1,3,4-tiadiaz?lio-2-aminida 1,3,4-triaz?lio-2-tiolato 1,2,3-oxadiazol-5-olato atividade antioxidante antitirosinase mesoionic compounds molecular rearrangement 1,3,4-thiadiazolium-2-aminide 1,2,3-oxadiazolium-5-olate antioxidant antitirosinase activities 1,3,4-triazolium-2-thiolate Qu?mica |
title_short |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
title_full |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
title_fullStr |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
title_full_unstemmed |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
title_sort |
Compostos mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase |
author |
Canuto, Andr? Vinicius dos Santos |
author_facet |
Canuto, Andr? Vinicius dos Santos |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Lima, Aurea Echevarria Aznar Neves |
dc.contributor.advisor1ID.fl_str_mv |
668.742.388-68 |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787205D1 |
dc.contributor.authorID.fl_str_mv |
109.818.207-35 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3300847150379345 |
dc.contributor.author.fl_str_mv |
Canuto, Andr? Vinicius dos Santos |
contributor_str_mv |
Lima, Aurea Echevarria Aznar Neves |
dc.subject.por.fl_str_mv |
compostos mesoi?nicos rearranjo molecular 1,3,4-tiadiaz?lio-2-aminida 1,3,4-triaz?lio-2-tiolato 1,2,3-oxadiazol-5-olato atividade antioxidante antitirosinase |
topic |
compostos mesoi?nicos rearranjo molecular 1,3,4-tiadiaz?lio-2-aminida 1,3,4-triaz?lio-2-tiolato 1,2,3-oxadiazol-5-olato atividade antioxidante antitirosinase mesoionic compounds molecular rearrangement 1,3,4-thiadiazolium-2-aminide 1,2,3-oxadiazolium-5-olate antioxidant antitirosinase activities 1,3,4-triazolium-2-thiolate Qu?mica |
dc.subject.eng.fl_str_mv |
mesoionic compounds molecular rearrangement 1,3,4-thiadiazolium-2-aminide 1,2,3-oxadiazolium-5-olate antioxidant antitirosinase activities 1,3,4-triazolium-2-thiolate |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
This work involved the study of the 1,3,4-thiadiazolium-2-amine mesoionic compounds class rearrangement, in the corresponding 1,3,4-triazolium-2-thiolate and the chemo-biological properties evaluation, such as antioxidant and antitirosinase activities. The mesoionic compounds generally possess structures which allow new heterocycles synthesis, and also interactions with biomolecules, such as DNA and proteins, which are important factors to explain their different biological activities. The mesoionic compounds studied in this work were the 1,3,4-triazolium-2-thiolate class obtained by the molecular rearrangement of their 1,3,4-thiadiazole-2-amine isomers in the presence of the nucleophilic solvents, under reflux and microwave irradiation. The 1,2,3- oxadiazolium-5-olate (sydnones) class were further synthesized. Mesoionic derivatives of the 1,3,4-thiadiazolium-2-aminide class, in hydrochloride form as well as a free base, and the 1,2,3-oxadiazolium-5-olate class were obtained by classical reactions already described in the literature. The use of microwave irradiation, in the presence of solid support and the Lewis acid, provided the mesoionic compounds 1,3,4-triazolium-2-tiolate in unprecedented quantitative yields, and much smaller reaction times (3 minutes) when compared to traditional methods (8 hours). Therefore, it presented high efficiency in molecular rearrangement. All synthesized mesoionic compounds were characterized by spectroscopic techniques, such as IR, UV, 1H and 13C NMR. The antioxidant activity evaluation of the mesoionic compounds showed to be promising for the 1,3,4-triazolium-2-thiolate and 1,3,4-thiadiazole-2-amine classes, especially in the hydrochloride form. The evaluation of the tyrosinase enzyme inhibition was performed to all synthesized compounds, but a higher activity was noticed in the 1,2,3-oxadiazole-5-olate class derivatives results. |
publishDate |
2009 |
dc.date.available.fl_str_mv |
2009-08-10 |
dc.date.issued.fl_str_mv |
2009-04-07 |
dc.date.accessioned.fl_str_mv |
2016-04-26T13:52:03Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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masterThesis |
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publishedVersion |
dc.identifier.citation.fl_str_mv |
CANUTO, Andr? Vinicius dos Santos. Compostos Mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase. 2009. 174 f. Disserta??o (Mestrado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/tede/25 |
identifier_str_mv |
CANUTO, Andr? Vinicius dos Santos. Compostos Mesoi?nicos: rearranjo molecular, atividade atioxidante e de inibi??o da Tirosinase. 2009. 174 f. Disserta??o (Mestrado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009. |
url |
https://tede.ufrrj.br/jspui/handle/tede/25 |
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por |
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por |
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openAccess |
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Universidade Federal Rural do Rio de Janeiro |
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Programa de P?s-Gradua??o em Qu?mica |
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UFRRJ |
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Brasil |
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Instituto de Ci?ncias Exatas |
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Universidade Federal Rural do Rio de Janeiro |
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