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dc.creatorMello, Débora Lombe de
dc.date.accessioned2019-08-19T18:08:59Z
dc.date.available2019-08-19T18:08:59Z
dc.date.issued2016-03-28
dc.identifier.urihttp://repositorio.ufsm.br/handle/1/17964
dc.description.abstractThis work describes the synthesis of 1H-pyrazole-1-thiocarboxamide, thiazol-1H-pyrazol-5-ol, 1H-pyrazol-1-yl-tiazoles and 1-(3-alkyl-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-alquen-1-ones were prepared from 1,1,1-trifluoro-4-methoxy-3-alquen-2-one lipophilic chains substituted (C6-C13) and hydrazides. The precursors 1,1,1-trifluoro-4-methoxy-3-Alquen-2-one [F3CCOCH=C(R)OCH3 where R = C6H13 (3a); C7H15 (3b); C8H17 (3c); C9H19 (3d ), C11H23 (3e); C13H27 (3f), (CH2) 2 Ph (3g)] were obtained in yields of 70-96%, by acylation reaction of the derivatives of the respective dimetoxicetais methyl ketones [2-octanone (1a), 2-nonanona (1b), 2-decanone (1c), 2-undecanone (1d), 2-tridecanone (1e), 2-pentadecanone (1f) and 4-phenyl-2-butanone (1g) with trifluoroacetic anhydride. These precursors 3a-g were cyclocondensed with semicarbazide hydrochloride to form the product 3-alkyl-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-carboxamides 4, with yields of 45-68%. The precursors 3a-g were subjected to cyclocondensation reaction with thiosemicarbazide and led to the formation of the series of products 3-alkyl-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide 5, in yields of 55-82%. This series 5 when reacted with α-bromoacetophenone led to bi-heterocyclic systems alkyl-3-1-(4-phenylthiazol-2-yl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-5-ol 6 with yield of 71-87% and 2-(3-alkyl-5-trifluoromethyl-1H-pyrazol-1-yl)-4-phenylthiazol 7, with yields of 68-89%. Finally, we investigated the reaction between 1,1,1-trifluoro-4-methoxy-3-alquen-2-one 3f and 3g with hydrazides obtained from natural fatty acids (palmitic, stearic and oleic), which allowed obtaining series of 1-(3-alkyl-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-alquen-1-ones 11f, 12f and 13f which R = C13H27; and 11g, 12g and 13g where R = (CH2)2Ph) with yields of 50-68%. The synthesis of these compounds applied the principles of green chemistry is the replacement of conventional organic solvents for green organic solvents such as ethanol. The compounds of the series 3 to 7 were evaluated for antimicrobial activity. As a result, the minimum inhibitory concentration (MIC) of 0.15 to 1.56 mg/mL inhibited the growth of bacteria and fungi. All synthesized compounds are novel and had their structures assigned by 1H, 13C NMR data and mass spectrometry data.eng
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESpor
dc.languageporpor
dc.publisherUniversidade Federal de Santa Mariapor
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subject1,1,1-trifluor-4-metóxi-3-alquen-2-onapor
dc.subject1H-pirazol-1-(tio)carboxamidapor
dc.subjectPirazoliltiazóispor
dc.subjectHidrazidas graxaspor
dc.subject1,1,1-trifluoro-4-methyl-3-alquen-2-oneeng
dc.subject1H-pyrazol-1-(thio) carboxamideeng
dc.subjectPyrazol-1-yl thiazoleseng
dc.subjectFatty hidrazideseng
dc.titleSíntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longaspor
dc.title.alternativeSynthesis, characterization and evaluation antimicrobial of new heterocycles nitrogenous using as precursors Β- -alkoxyvinyl trifluoromethyl ketone chains alkyl longeng
dc.typeTesepor
dc.description.resumoEste trabalho descreve a síntese de 1H-pirazol-1-(tio)carboxamidas, tiazol-1H-pirazol-5-ol, 1H-pirazol-1-il-tiazóis e 1-(3-alquil-5-trifluormetil-5-hidroxi-4,5-di-idro-1H-pirazol-1-il)-alquen-1-onas a partir de 1,1,1-trifluor-4-metóxi-3-alquen-2-ona substituídas com cadeias lipofílicas (C6-C13) e hidrazidas. Os precursores 1,1,1-trifluor-4-metóxi-3-alquen-2-ona [F3CCOCH=C(R)OCH3, onde R = C6H13 (3a); C7H15 (3b); C8H17 (3c); C9H19 (3d); C11H23 (3e); C13H27 (3f); (CH2)2Ph (3g)] foram obtidos em rendimentos entre 70-96%, através da reação de acilação dos dimetoxicetais derivados das respectivas metilcetonas [2-octanona (1a), 2-nonanona (1b), 2-decanona (1c), 2-undecanona (1d), 2-tridecanona (1e), 2-pentadecanona (1f) e 4-fenil-2-butanona (1g) com anidrido trifluoracético. Esses precursores 3a-g foram ciclocondensados com cloridrato de semicarbazida para formação dos produtos 3-alquil-5-trifluormetil-5-hidroxi-4,5-di-idro-1H-pirazol-1-carboxamidas 4, com rendimentos de 45-68%. Os precursores 3a-g foram submetidos a reações de ciclocondensação com tiosemicarbazida e conduziram à formação da série de produtos 3-alquil-5-hidroxi-5-trifluormetil-4,5-di-idro-1H-pirazol-1-tiocarboxamida 5, em rendimentos de 55-82%. A série 5 reagiu com α-bromoacetofenona levando aos sistemas bi-heterociclos 3-alquil-1-(4-feniltiazol-2-il)-5-trifluormetil-5-hidroxi-4,5-di-idro-1H-pirazol-5-ol 6 em rendimentos de 71-87% ou 2-(3-alquil-5-trifluormetil-1H-pirazol-1-il)-4-feniltiazol 7, com rendimentos de 68-89%. Por fim, foi investigada a reação entre as 1,1,1-trifluor-4-metóxi-3-alquen-2-ona 3f e 3g com hidrazidas obtidas de ácidos graxos naturais (palmítico, esteárico e oleico), a qual possibilitou obtenção da série de 1-(3-alquil-5-trifluormetil-5-hidroxi-4,5-di-idro-1H-pirazol-1-il)-alquen-1-onas 11f, 12f e 13f onde R = C13H27; e 11g, 12g e 13g onde R = (CH2)2Ph) com rendimentos de 50-68%. A síntese desses compostos aplicou um dos princípios da química verde que é a substituição de solventes orgânicos convencionais por solventes orgânicos verdes, como etanol. Os compostos das séries 3 a 7 foram avaliadas quanto à atividade antimicrobiana. Como resultado, a concentração inibitória mínima (CIM) entre 0,15-1,56 mg/mL inibiu o crescimento de bactérias e fungos. Todos os compostos sintetizados são inéditos e tiveram suas estruturas atribuídas por dados de RMN 1H, 13C e espectrometria de massas.por
dc.contributor.advisor1Flores, Alex Fabiani Claro
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/1159954352174167por
dc.contributor.referee1Fernandes, Liana da Silva
dc.contributor.referee1Latteshttp://lattes.cnpq.br/0573570242395130por
dc.contributor.referee2Rodrigues, Oscar Endrigo Dorneles
dc.contributor.referee2Latteshttp://lattes.cnpq.br/6536519955416085por
dc.contributor.referee3Fantinel, Leonardo
dc.contributor.referee3Latteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4777461U9por
dc.contributor.referee4Mostardeiro, Marco Aurelio
dc.contributor.referee4Latteshttp://lattes.cnpq.br/6195396264565980por
dc.creator.Latteshttp://lattes.cnpq.br/0395675025653002por
dc.publisher.countryBrasilpor
dc.publisher.departmentQuímicapor
dc.publisher.initialsUFSMpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
dc.subject.cnpqCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICApor
dc.publisher.unidadeCentro de Ciências Naturais e Exataspor


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