Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / The present research describes the use of b-alcoxyvynil
trihalomethyl ketones [CX3C(O)CR2CR1R, where X= Cl, F; R= OMe, OEt; R1: H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh; R2= H, Ph] in the regiospecific synthesis of 16 new 3(4)-alkyl(aryl) substituted 5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-1-tosylpyrazoles. These pyrazolines were obtained from the reaction of b-alcoxyvinyl trihalomethyl ketones with tosyl hydrazine (63-92%). In a following phase, aiming to develop an efficient methodology of dehydration. Two 4-methoxy-4-(4-fluorophenyl)-1,1,1-trihalo-3-buten-2-ones were submitted to the reactions with four dinucleophile: semicarbazide hydrochloride, thiosemicarbazide, methyl hydrazinocarboxylate and 2-furoic hydrazide furnishing, eigth new 1-substituted-3-(4-fluorophenyl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles (63-98%). The dehydration reactions carried out in thionyl chloride/pyridine/benzene gave the best yields of 3-(4-fluorophenyl)-5-trihalomethyl-1H-pyrazoles (41-75%). The inhibitory activities of pyrazolinic compounds were tested using the autobiography technique for bacteria and fungis. The tosyl pyrazolinic compounds exhibit a significant activity for gram-positive bacteria and low activity to fungi. Among the tested compounds, 3-(4-fluorphenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-tosylpyrazole exhibited the best inhibitory activity against Staphylococcus aureus (0,78 μg/μL). All the compounds were characterized by spectral and analytical experiments 1H s and 13C s NMR, and the purity was demostrated by elemental analyzes and CG/MS. / O presente trabalho descreve a utilização de b-alcoxivinil
trialometil cetonas [CX3C(O)CR2CR1R, onde X: Cl, F; R: OMe, OEt; R1: H, Me, Ph, 4-MePh, 4-MeOPh, 4-BrPh, 4-ClPh, 4-FPh; R2: H, Ph] na síntese regioespecífica de 16 novos 3(4)-alquil(aril)-5-trialometil-5-hidroxi-4,5-diidro-1H-1-tosilpirazois. As tosilpirazolinas foram obtidas a partir da reação das b-alcoxivinil trialometil cetonas com tosilhidrazina (63-92%). Em uma segunda etapa, visando desenvolver uma eficiente metodologia para desidratação das pirazolinas trialometil substituídas. Duas 4-metoxi-4-(4-fluorfenil)-1,1,1-trialo-3-buten-2-onas foram submetidas a reações com quatro dinucleófilos: cloridrato de semicarbazida, tiosemicarbazida, carboximetilhidrazina e 2-furanoilhidrazina, originando inicialmente 8 novos 3-(4-fluorfenil)-5-trialometil-5-hidroxi-4,5-diidro-1H-pirazóis (63-98%). As reações de desidratação realizadas em meio cloreto de tionila/piridina/benzeno produziram os melhores rendimentos para 6 novos 3-(4-fluorfenil)-5-trialometil-1H-pirazóis (41-75%). As atividades inibitórias dos compostos foram avaliadas frente bactérias e fungos, utilizando a técnica de autobiografia. Os compostos tosil pirazolínicos evidenciaram significante atividade frente a bactérias gram-positivas e pouco ativas para fungos. Dentre os compostos avaliados, o composto 3-(4-fluorfenil)-5-hidroxi-5-trifluormetil-4,5-diidro-1H-1-tosilpirazol apresentou o melhor resultado, inibindo o crescimento de Staphylococcus áureus (0,78 μg/μL). Os compostos foram caracterizados por experimentos de RMN de 1H e 13C, e sua pureza determinada via Análise Elementar e CG/MS.
| Identifer | oai:union.ndltd.org:IBICT/oai:repositorio.ufsm.br:1/4305 |
| Date | 02 February 2006 |
| Creators | Wentz, Alexandre Pereira |
| Contributors | Bonacorso, Helio Gauze, Martins, Marcos Antonio Pinto, Zanatta, Nilo, Ferreira, Juliano |
| Publisher | Universidade Federal de Santa Maria, Programa de Pós-Graduação em Química, UFSM, BR, Química |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf |
| Source | reponame:Repositório Institucional da UFSM, instname:Universidade Federal de Santa Maria, instacron:UFSM |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 100600000000, 400, 300, 300, 300, 300, 500, 06c852ad-d805-43c3-99d6-93a6a86f507c, 95965dc3-274e-4381-a0d9-16fa9af2e4db, a8bc3c8e-4034-458b-a211-6be4a0d7001b, 2f7bd6ce-78fa-4968-ac66-2d1407e90f60, 25bd8677-6c2e-4742-9b65-d2ae877f92b2 |
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