Síntese de calcogenil-1,2,3-triazóis derivados de bases nitrogenadas e avaliação das propriedades toxicológicas

• Ano de defesa: 2024
• Autor(a) principal: Gutterres, Elba Lixinski
• 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: Organocalcogênio; Heterociclo; Propriedades toxicológicas; Bases nitrogenadas; Organochalcogen; Heterocycle; Toxicological properties; Nitrogenous bases; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/33217

This work reports the synthesis of 1,4-disubstituted bis-(chalcogenyl-1,2,3-triazoles) using 1,3-di(propargyl)-6-methyluracil and alkylchalcogenated azides employing copper(II) sulfate pentahydrate as catalyst and sodium ascorbate as reducing agent. The reactions were carried out in a 2:1 mixture of dimethylformamide and water as solvent at room temperature, with reaction times ranging from 7 h to 12 h. The same protocol was extended to the formation of mono-chalcogenyl-1,2,3-triazoles derived from theobromine, using propargylated theobromine and alkylchalcogenated azides. Through this methodology, it was possible to synthesize seven new examples, five bis-triazoles derived from uracil and two mono-triazoles derived from theobromine, with yields of 33-92%. The methodology proved to be versatile for the formation of products with electron-donating and electron-withdrawing substituents, sterically hindered groups, and organoselenium and organosulfur groups. In addition, preliminary in vitro tests of four synthesized compounds demonstrated high cell viability, indicating that the compounds are safe for use as potential pharmaceuticals. Two of the compounds tested showed protective effect and potential antioxidant tendency in the lipid peroxidation test.