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dc.contributor.authorPissinate, Kenia
dc.date.accessioned2023-12-21T18:59:00Z-
dc.date.available2023-12-21T18:59:00Z-
dc.date.issued2010-08-27
dc.identifier.citationPissinate, Kenia. Síntese e correlação entre a estrutura e a atividade leishmanicida de novas amidas estiril-substituídas. 2010. 160 f. Tese (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica.por
dc.identifier.urihttps://rima.ufrrj.br/jspui/handle/20.500.14407/10204-
dc.description.abstractEste trabalho relata a preparação de 25 estiril-amidas das quais 8 são inéditas, obtidas através da reação de substituição nucleofílica, via formação do cloreto de ácido, dos ácidos estiril-substituídos com os nucleófilos benzilamina, fenetilamina, 3,4-dimetoxifenetilamina, 3,4-metilenodioxifenetilamina em bons rendimentos. Também foram obtidos derivados N-estiril-N,N’-diciclo-hexil-uréias, via reação de acoplamento com a DCC. Além disso, foram preparados 5 compostos derivados da piperina, amida alcaloidal majoritária de Piper nigrum, sendo 4 deles inéditos na literatura. As técnicas espectroscópicas de IV e RMN de 1H e 13C foram utilizadas para caracterizar os produtos obtidos. Averiguou-se a biodisponibilidade em meio aquoso para os ensaios in vitro das estiril-amidas substituídas em três tipos de veículos (SME, PVP e -CD). Foi realizado, também o estudo da atividade citotóxica das estiril-amidas substituídas frente à forma promastigota de Leishmania amazonensis e às células de macrófagos de camundongo, além da inibição enzimática frente a DNA topoisomerase II- Os ensaios leishmanicidas mostraram que a série estiril-5’-6’-dimetoxifenetilamidas foi a mais citotóxica, apresentando uma maior seletividade diante dos macrófagos. As séries das estiril-benzil e fenetil-amidas apresentaram correlações lineares entre os valores de logP e os % de inibição frente a L. amazonensis na concentração de 50M. Pôde-se observar que, de maneira geral, os veículos CD e PVP contribuíram para a biodisponibilização das amidas independentemente do efeito eletrônico do substituinte. As estiril-amidas, em sua grande maioria, inibiram a atividade enzimática da topoisomerase II-.por
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior, CAPES, Brasil.por
dc.formatapplication/pdf*
dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.rightsAcesso Abertopor
dc.subjectestiril-amidaspor
dc.subjectatividade leishmanicidapor
dc.subjectDNA topoisomerase II-por
dc.subjectstyryl-amideseng
dc.subjectantileishmania activityeng
dc.subjectDNA-topoisomerase II-eng
dc.titleSíntese e correlação entre a estrutura e a atividade leishmanicida de novas amidas estiril-substituídaspor
dc.typeTesepor
dc.description.abstractOtherIn this work describes the preparation of styryl-25 amides of which eight are new. The amides were obtained in good yields, by nucleophilic substitution reaction through formation of acid chlorides, by reacting styryl-substituted acids with the nucleophiles benzylamine, phenethylamine, 1,3-benzodioxolphenethylamine and 3,4-dimethoxiphenethylamine. Derivatives N-styryl-N,N'-dicyclo-hexyl-ureas were also obtained by coupling reaction with DCC. In addition, five compounds derivated from piperine, amide alkaloidal majority of Piper nigrum, were prepared, 4 of them new. The spectroscopic techniques IV and RMN 1H and 13C were used to characterize the products obtained. The bioavailability in aqueous medium for in vitro tests of styryl-substituted amides in three types of vehicles (EMS, PVP and -CD) was tested. The cytotoxicity of styryl-substituted amides for the promastigote form of Leishmania amazonensis and mouse macrophage cells was studied, as well as the enzyme inhibition against DNA topoisomerase II-  The antileishmanial tests showed that the series-styryl 5'-6'-dimetoxifenetilamidas was the most cytotoxic, showing a higher selectivity for the macrophages. The series of styryl-benzyl and phenethyl-amide showed linear correlations between the logP values and % inhibition against L. amazonensis at a concentration of 50 M. It was observed that, in general, vehicles CD and PVP contributed to the bioavailability of amides regardless of the electronic effect of the substituent. The styryl-amides, for the most part, inhibited the enzymatic activity of topoisomerase II-.eng
dc.contributor.advisor1Lima, Aurea Echevarria Aznar Neves
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/1879077396134052por
dc.contributor.advisor-co1Lima, Marco Edilson Freire de
dc.contributor.referee1Maciel, Maria Aparecida M.
dc.contributor.referee2Lima, Débora Decote Ricardo de
dc.contributor.referee3Oliveira, Mácia Cristina de
dc.contributor.referee4Lima, Célio Freire de
dc.contributor.referee5Castro, Rosane Nora
dc.creator.Latteshttp://lattes.cnpq.br/8512959642500378por
dc.publisher.countryBrasilpor
dc.publisher.departmentInstituto de Ciências Exataspor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
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