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dc.creatorBorchhardt, Deise Moreira
dc.date.accessioned2017-05-15
dc.date.available2017-05-15
dc.date.issued2007-03-01
dc.identifier.citationBORCHHARDT, Deise Moreira. Synthesis and interactions studies of 3-phosphate- and 3-phosphonamide-4,4,4-trifluoro-but-1-yl-carbamic acid ethyl esters with acetylcholinesterase enzyme and synthesis of 3-carboxyethyl- and 3-pyrimidin-2-yl-2-oxo-6-trifluoromethyl-[1,2,3]oxathiazinanes. 2007. 202 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2007.por
dc.identifier.urihttp://repositorio.ufsm.br/handle/1/4300
dc.description.abstractA 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.eng
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico
dc.formatapplication/pdfpor
dc.languageporpor
dc.publisherUniversidade Federal de Santa Mariapor
dc.rightsAcesso Abertopor
dc.subjectQuímicapor
dc.subjectQuímica orgânicapor
dc.subjectSíntese químicapor
dc.subjectEnzima acetilcolinesterasepor
dc.titleSíntese 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]oxatiazinanaspor
dc.title.alternativeSynthesis and interactions studies of 3-phosphate- and 3-phosphonamide-4,4,4-trifluoro-but-1-yl-carbamic acid ethyl esters with acetylcholinesterase enzyme and synthesis of 3-carboxyethyl- and 3-pyrimidin-2-yl-2-oxo-6-trifluoromethyl-[1,2,3]oxathiazinaneseng
dc.typeTesepor
dc.description.resumoUma série de [3-(fosfato)-4,4,4-trifluor-but-1-il]-carbamatos de etila e [3-(fosfonamida)-4,4,4-trifluor-but-1-il]-carbamatos de etila foram obtidos a partir da reação de g-amino álcoois (4,4,4-trifluor-3-hidróxi-butan-1-il)-carbamatos de etila com oxicloreto de fósforo na presença de base e subseqüente reação com álcoois ou aminas. Este trabalho apresenta também a síntese e caracterização de 3-carboxietil-2-oxo-6-trifluormetil-[1,2,3]oxatiazinanas e 3-[pirimidin-2-il]-2-oxo-6-trifluormetil-[1,2,3]oxatiazinanas obtidas por reação de ciclização dos g-amino álcoois (4,4,4-trifluor-3-hidróxi-butan-1-il)-carbamatos de etila e 4-(pirimidin-2-ilamino)-1,1,1-trifluor-butan-2-ols com cloreto de tionila na presença de base. Os g-amino álcoois utilizados neste trabalho foram obtidos por rotas sintéticas que tem como precursor as b-alcoxivinil trifluormetil cetonas de fórmula geral F3CC(O)CH=C(R)OR1, onde R = H, Me, Pr, Bu, Ph, 4-Me-Ph; R1 = Me, Et. As b-alcoxivinil trifluormetil cetonas utilizadas foram obtidas através de acilação de acetais ou enol éteres com anidrido trifluoracético. O efeito dos carbamatos contendo grupo fosfato na inibição da enzima acetilcolinesterase foi avaliado. Vários compostos apresentaram inibição significante dessa enzima e estudos de modelagem molecular foram desenvolvidos para elucidar o modo de interação destes novos inibidores. As oxatiazinanas foram testadas na inibição do crescimento de microorganismos incluindo leveduras como fungos, bactérias e alga, porém, não apresentaram atividade inibitóriapor
dc.contributor.advisor1Zanatta, Nilo
dc.contributor.advisor1Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9por
dc.contributor.referee1Zoch, Alana Neto
dc.contributor.referee1Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782125E2por
dc.contributor.referee2Schetinger, Maria Rosa Chitolina
dc.contributor.referee3Flores, Alex Fabiani Claro
dc.contributor.referee3Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0por
dc.contributor.referee4Martins, Marcos Antonio Pinto
dc.contributor.referee4Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783192P3por
dc.creator.Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4702323H3por
dc.publisher.countryBRpor
dc.publisher.departmentQuímicapor
dc.publisher.initialsUFSMpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
dc.subject.cnpqCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICApor


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