Síntese e caracterização de 1,3,4-oxadiazolil-1,2,4-oxadiazóis derivados de ácidos acrílicos 3-substituídos

• Ano de defesa: 2017
• Autor(a) principal: Mayer, João Cândido Pilar
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; Brasil; Química; UFSM; Programa de Pós-Graduação em Química; Centro de Ciências Naturais e Exatas
• Palavras-chave em Português: Oxadiazóis; Ácidos acrílicos; Ferroceno; UV-Vis; Voltametria; Oxadiazoles; Acrylic acids; Ferrocene; Voltammetry; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/13682

A series of 1,3,4-oxadiazolyl-1,2,4-oxadiazoles was synthesized through a one-pot condensation-cyclization reaction between 3-substituted acrylic acids and 5-aryl-1,2,4-oxadiazolyl-1,2,4-oxadiazoles, and were characterized through 1H NMR, 13C NMR, X-ray diffraction and HRMS. Products were obtained in rather variable yields (23 – 87 %). The cited compounds were compared to single heterocycle-containing (1,3,4-oxadiazole) examples in order to measure the influence of the 1,2,4-oxadiazole, as well as the substituents’, on the molecules. After a simple comparison of 1H NMR signs between cinnamic acid derivatives, two series of (E)-3-ferrocenylacrylic acid derivatives were characterized through UV-Vis spectroscopy and cyclic voltammetry. They were also tested for ct-DNA interaction, displaying strong interaction (K~106 M-1) with it. Finally, crotonic acid derivatives were reactive to the aminoacid cysteine, giving a series of adducts, which suggests a possible activity in future biological tests.