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Previous issue date: 2012-08-03 / Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gico - CNPq / Nowadays the demand for cleaner and more efficient synthetic processes have been deemed very important, especially due to environmental aspects. Thus, this thesis describes the synthesis of a series of 20 tiossemicarbazidas, nine class of N4-substituted obtained from the reaction of isothiocyanates with different hydrazine hydrate and eleven Class of N1,N4-disubstituted obtained from the reaction of isothiocyanates with different phenyl hydrazine. We used the traditional method by stirring at room temperature, the microwave irradiation and solid-solid maceration for preparing such compounds, the latter methodology to that presented the best performances for the compounds synthesized in only two minutes of reaction. The antioxidant activity of tiossemicarbazidas was evaluated experimentally by the method of DPPH, indicating significant activity for most of the derivatives tested.
The tiossemicarbazidas N4-substituted synthetic precursors were derived from the class of 36 thiosemicarbazones, which have also been obtained by three different methodologies from the reaction of different aromatic aldehydes with tiossemicarbazidas N4-substituted. The methodology used by traditional reflux, the microwave irradiation in the presence of organic solvent and microwave irradiation in the absence of solvent, the latter method was allowed to obtain products with better results with only 3 minutes of reaction. All 36 of thiosemicarbazones derivatives were tested against the fungi Candida albicans and Aspergillus parasiticus, with moderate activity for some of the derivatives tested.
The tiossemicarbazidas N1,N4-disubstituted are synthetic precursors of the 1,3,4-thiadiazolium-2-aminide hydrochlorides mesoionic class. Eleven mesoionic derivatives were obtained by microwave irradiation, from tiossemicarbazidas N1,N4-disubstituted with different aromatic aldehydes. We also evaluated the cytotoxic activities from some of the synthesized mesoionic lines K562 human leukemia and Jurkat, as well as in the line of Daudi lymphoma, obtaining satisfactory and very promising results for some of the compounds tested. Furthermore, the compounds mesoionic were tested for in vivo activity against L. amazonensis and L. infantum and also opposite the trypanothione reductase enzyme L. amazonensis, L. infantum, L. braziliensis and T. cruzi showing significant activity indicating the potential use of these compounds as anti-parasitic agents / Nos dias atuais as demandas por processos sint?ticos mais limpos e eficientes t?m sido consideradas muito relevantes, devido especialmente aos aspectos ambientais. Assim, este trabalho de tese relata a s?ntese de uma s?rie de 20 tiossemicarbazidas, sendo nove da classe das N4-substitu?das, obtidas a partir da rea??o de diferentes isotiocianatos com hidrazina hidrato e onze da classe das N1,N4-dissubstitu?das obtidas a partir da rea??o de diferentes isotiocianatos com fenil hidrazina. Utilizou-se a metodologia tradicional por agita??o a temperatura ambiente, a irradia??o de micro-ondas e a macera??o s?lido-s?lido para a prepara??o desses compostos, sendo esta ?ltima metodologia a que apresentou os melhores rendimentos para os compostos sintetizados em apenas 2 minutos de rea??o. A atividade antioxidante das tiossemicarbazidas foi avaliada experimentalmente pelo m?todo do DPPH, indicando atividade significativa para a maioria dos derivados testados.
As tiossemicarbazidas N4-substitu?das foram os precursores sint?ticos de 36 derivados da classe das tiossemicarbazonas, que tamb?m foram obtidas por tr?s metodologias diferentes a partir da rea??o de diferentes alde?dos arom?ticos com as tiossemicarbazidas N4-substitu?das. Utilizou-se a metodologia tradicional por refluxo, a irradia??o de micro-ondas na presen?a de solvente org?nico e a irradia??o de micro-ondas na aus?ncia de solvente, esta ?ltima metodologia foi a que permitiu a obten??o dos produtos com melhores rendimentos em apenas 3 minutos de rea??o. Todos os 36 derivados das tiossemicarbazonas foram testados frente aos fungos Aspergillus parasiticus e Candida albicans, apresentando moderada atividade para alguns dos derivados ensaiados.
As tiossemicarbazidas N1,N4-dissubstitu?das foram os precursores sint?ticos dos cloridratos mesoi?nicos da classe 1,3,4-tiadiaz?lio-2-aminida. Onze derivados mesoi?nicos foram obtidos via irradia??o de micro-ondas, a partir das tiossemicarbazidas N1,N4-dissubstitu?das com diferentes alde?dos arom?ticos. Foram avaliadas, tamb?m, as atividades citot?xicas de alguns dos mesoi?nicos sintetizados nas linhagens leuc?micas humanas K562 e Jurkat, assim como na linhagem de linfoma Daudi, obtendo-se resultados bastante promissores e satisfat?rios para alguns dos compostos ensaiados. Al?m disso, os compostos mesoi?nicos foram ensaiados quanto ? atividade in vivo frente a L. amazonensis e L. infantum e tamb?m frente ? enzima tripanotiona redutase de L. amazonensis, L. infantum, L. braziliensis e T. cruzi mostrando atividade significativa indicando a potencial utiliza??o desses compostos como agentes anti-parasit?rios.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/1584 |
| Date | 03 August 2012 |
| Creators | Reis , Camilla Moretto dos |
| Contributors | Lima, Aurea Echevarria Aznar Neves, Souza, Andrea Luzia Ferreira de, Souza, Maria Cec?lia Bastos Vieira de, Graebin, Cedric Stephan, Del Cistia, Catarina De Nigris, Santos, Andressa Esteves de Souza dos |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
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