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dc.creatorFerreira, Welisson da Silva-
dc.creator.Latteshttp://lattes.cnpq.br/2399464111506427por
dc.contributor.advisor1Lima, Marco Edilson Freire de-
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/8392420706762318por
dc.contributor.referee1Coelho, Fernando Antônio Santos-
dc.contributor.referee2Dias, Ayres Guimarães-
dc.contributor.referee3Nimrichter, Leonardo-
dc.contributor.referee4Graebin, Cedric Stephan-
dc.date.accessioned2019-09-16T15:54:51Z-
dc.date.issued2014-11-14-
dc.identifier.citationFerreira, Welisson da Silva. Planejamento, síntese e avaliação das atividades antifúngica e tripanocida da piperina e derivados do núcleo 1,3,4-Oxadiazol-2-Tiona. 2014. [251 f]. Tese( Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, [Seropédica-RJ] .por
dc.identifier.urihttps://tede.ufrrj.br/jspui/handle/jspui/2895-
dc.description.resumoO desenvolvimento deste trabalho faz parte de uma linha de pesquisa que visa utilizar produtos naturais abundantes e accessíveis, que já possuam atividades biológicas relevantes descritas, como matéria-prima e fonte inspiradora de estruturas na síntese de novos derivados e análogos com potencial antifúngico e antichagásico. A piperina, extraída da pimenta do reino, bem como alguns derivados e análogos, preparados pelo nosso grupo de pesquisa, demonstraram efeito tóxico sobre o Trypanosoma cruzi, agente etiológico da Doença de Chagas. Além da atividade tóxica frente a protozoários, também é descrita para este produto natural a atividade antifúngica, entre outras. Descrevemos aqui o planejamento, a síntese e a caracterização de 19 novos derivados e análogos da piperina, bem como a avaliação da atividade destes contra epimastigotas do T. cruzi, contra cepas do fungo Cryptococcus neoformans e a avaliação da citotoxicidade frente a células humanas. Para todos os compostos preparados foi homologado o heterociclo da classe 1,3,4-oxadiazol-2-tiona, descrito como unidade farmacofórica para a atividade antifúngica. Os resultados obtidos nas avaliações biológicas realizadas indicam que os derivados 89 e 90 apresentam as melhores atividades contra o T. cruzi. O derivado 90 apresenta o melhor perfil antifúngico, apresentando atividade comparável ao fármaco fluconazol nos ensaios realizados. Estudos sobre a interferência destes compostos no perfil lipídico da membrana do T. cruzi e do C. neoformans, sugerem que este possa ser um dos mecanismos de ação destes derivados. O conjunto de resultados descritos, indicam que os derivados 89 (insaturado) e 90 (saturado), ambos com 4 carbonos na cadeia espaçadora e com estruturas mais semelhantes à amida natural, apresentam as melhores atividades antiparasitária e antifúngica, respectivamente, validando o planejamento realizado neste trabalho.por
dc.description.abstractThis work is part of a research program that aims to use abundant and accessible natural products that show relevant biological activities as starting material and source of inspiring in the synthesis of new derivatives and analogues with antifungal and/or antichagasic potential. Piperine, extracted from black pepper as well as some derivatives and analogues prepared by our research group, showed toxic effect against Trypanosoma cruzi, the etiologic agent of Chagas disease. Apart its toxic activity against protozoa, it is also described antifungal activity for this natural product, among others. We describe herein the design, synthesis and the characterization of 19 new derivatives and analogues of piperine as well as the evaluation of their activities against epimastigotes of T. cruzi and as well as strains of the fungus Cryptococcus neoformans. The cytotoxicity of all the synthesized compounds were evaluated of against human cells. In the structure of all the prepared compounds has been inserted the 1,3,4-oxadiazole-2-thione portion, described as pharmacophoric unit for antifungal activity. The biological results obtained indicate that the oxadiazolic derivatives 89 and 90 show the best activity against T. cruzi epimastigotes. The derivative 90 showed the best antifungal profile, comparable to fluconazole. Studies on the interference of these compounds on lipid profile of the T. cruzi membrane and C. neoformans, suggest that this may be one of the mechanisms of action of these derivatives. The assembly of results described herein indicate that the derivatives 89 (unsaturated) and 90 (saturated), both with 4 carbons in the spacer chain and most similar structures to the natural amide, featuring the best antiparasitic and antifungal activities, respectively, validating the molecular planning done in this studyeng
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dc.description.provenanceMade available in DSpace on 2019-09-16T15:54:51Z (GMT). No. of bitstreams: 1 2014 - Welisson da Silva Ferreira.pdf: 5568636 bytes, checksum: b2e63d949960a75fd37bccaecd81d064 (MD5) Previous issue date: 2014-11-14eng
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico - CNPQpor
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dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.publisher.departmentInstituto de Ciências Exataspor
dc.publisher.countryBrasilpor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
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dc.rightsAcesso Abertopor
dc.subjectQuímica Orgânicapor
dc.subjectSíntese Orgânicapor
dc.subjectPiperaceaepor
dc.subjectFungicidaspor
dc.subjectTrypanossoma Cruzipor
dc.subjectCryptococcus neoformanspor
dc.subjectOrganic Chemistryeng
dc.subjectOrganic Synthesiseng
dc.subjectFungicideseng
dc.subject.cnpqQuímicapor
dc.titlePlanejamento, síntese e avaliação das atividades antifúngica e tripanocida da piperina e derivados do núcleo 1,3,4-Oxadiazol-2-Tionapor
dc.title.alternativePlanning, synthesis and evaluation of the antifungal and trypanocidal activities of piperine and 1,3,4-Oxadiazol-2-Tione nucleus derivativeseng
dc.typeTesepor
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