Síntese e estudo das interações de 3-(fosfato)- e 3-(fosfonamida)-4,4,4-trifluor-but-1-il-carbamatos de etila com a enzima acetilcolinesterase e síntese de 3-carboxietil- e 3-pirimidin-2-il-2-oxo-6-trifluormetil-[1,2,3]oxatiazinanas

• Ano de defesa: 2007
• Autor(a) principal: Borchhardt, Deise Moreira
• Orientador(a): Zanatta, Nilo
• Banca de defesa: Zoch, Alana Neto , Schetinger, Maria Rosa Chitolina , Flores, Alex Fabiani Claro , Martins, Marcos Antonio Pinto
• Tipo de documento: Tese
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química
• Departamento: Química
• País: BR
• Palavras-chave em Português: Química; Química orgânica; Síntese química; Enzima acetilcolinesterase
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/4300

A series of [3-(phosphate)-4,4,4-trifluoro-but-1-yl]-carbamic acid ethyl ester and [3-(phosphonamide)-4,4,4-trifluoro-but-1-yl]-carbamic acid ethyl ester obtained from the reaction of g-amino alcohols (4,4,4-trifluoro-3-hydroxy-butan-1-yl)-carbamic acid ethyl ester with phosphorus oxychloride in the presence of base and subsequent reaction with alcohols or amines. In addition, this work describes the synthesis and characterization of 3-carboxyethyl-2-oxo-6-trifluoromethyl-[1,2,3]oxathiazinanes and 3-[pyrimidin-2-yl]-2-oxo-6-trifluoromethyl-[1,2,3]oxathiazinanes obtained from the cyclization reaction of the g-amino alcohols (4,4,4-trifluoro-3-hydroxy-butan-1-yl)-carbamic acid ethyl ester and 4-(pyrimidin-2-ylamino)-1,1,1-trifluoro-butan-2-ols with thionyl chloride in the presence of a base. The g-amino alcohols used in this work were obtained from synthetic routes using as precursor b-alkoxyvinyl trifluoromethyl ketones with general formula F3CC(O)CH=C(R)OR1, where R = H, Me, Pr, Bu, Ph, 4-Me-Ph; R1 = Me, Et. The b-alkoxyvinyl trifluoromethyl ketones were obtained from the acylation of acetals or enolethers with trifluoroacetic anhydride. The effect of the carbamates containing phosphate group in the inhibition of acetylcholinesterase enzyme was tested. Several compounds exhibited significant inhibition of this enzyme. Molecular modeling studies were developed to elucidate the interaction mode of these new inhibitors. The oxathiazinanes were assessed against a panel of microorganisms including yeast like fungi, bacteria and algae, but no activity was found.