Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano
Autor(a) principal: | |
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Data de Publicação: | 2006 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/4305 |
Resumo: | 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. |
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2017-05-102017-05-102006-02-02WENTZ, Alexandre Pereira. Synthesis and structural characterization of trihalomethyl substituted pyrazolynil-tolylsulfones of antimicrobial interest. 2006. 158 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2006.http://repositorio.ufsm.br/handle/1/4305The 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.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaSíntese químicaCompostos químicosMedicamentos antimicrobianosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobianoSynthesis and structural characterization of trihalomethyl substituted pyrazolynil-tolylsulfones of antimicrobial interestinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Martins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Ferreira, Julianohttp://lattes.cnpq.br/2694197910478313http://lattes.cnpq.br/1723701471630239Wentz, Alexandre Pereira10060000000040030030030030050006c852ad-d805-43c3-99d6-93a6a86f507c95965dc3-274e-4381-a0d9-16fa9af2e4dba8bc3c8e-4034-458b-a211-6be4a0d7001b2f7bd6ce-78fa-4968-ac66-2d1407e90f6025bd8677-6c2e-4742-9b65-d2ae877f92b2info:eu-repo/semantics/openAccessreponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALWentz_Alexandre.pdfWentz_Alexandre.pdfapplication/pdf4410251http://repositorio.ufsm.br/bitstream/1/4305/1/Wentz_Alexandre.pdf825075b16a8ab0b1fc25d402ad3afa7eMD511/43052023-03-03 10:28:34.907oai:repositorio.ufsm.br:1/4305Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestouvidoria@ufsm.bropendoar:39132023-03-03T13:28:34Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
dc.title.alternative.eng.fl_str_mv |
Synthesis and structural characterization of trihalomethyl substituted pyrazolynil-tolylsulfones of antimicrobial interest |
title |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
spellingShingle |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano Wentz, Alexandre Pereira Química Química orgânica Síntese química Compostos químicos Medicamentos antimicrobianos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
title_full |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
title_fullStr |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
title_full_unstemmed |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
title_sort |
Síntese e caracterização estrutural de pirazolinil-tolil-sulfonas trialometil substituídas de interesse antimicrobiano |
author |
Wentz, Alexandre Pereira |
author_facet |
Wentz, Alexandre Pereira |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee3.fl_str_mv |
Ferreira, Juliano |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/2694197910478313 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1723701471630239 |
dc.contributor.author.fl_str_mv |
Wentz, Alexandre Pereira |
contributor_str_mv |
Bonacorso, Helio Gauze Martins, Marcos Antonio Pinto Zanatta, Nilo Ferreira, Juliano |
dc.subject.por.fl_str_mv |
Química Química orgânica Síntese química Compostos químicos Medicamentos antimicrobianos |
topic |
Química Química orgânica Síntese química Compostos químicos Medicamentos antimicrobianos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
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. |
publishDate |
2006 |
dc.date.issued.fl_str_mv |
2006-02-02 |
dc.date.accessioned.fl_str_mv |
2017-05-10 |
dc.date.available.fl_str_mv |
2017-05-10 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
WENTZ, Alexandre Pereira. Synthesis and structural characterization of trihalomethyl substituted pyrazolynil-tolylsulfones of antimicrobial interest. 2006. 158 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2006. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4305 |
identifier_str_mv |
WENTZ, Alexandre Pereira. Synthesis and structural characterization of trihalomethyl substituted pyrazolynil-tolylsulfones of antimicrobial interest. 2006. 158 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2006. |
url |
http://repositorio.ufsm.br/handle/1/4305 |
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por |
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100600000000 |
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Química |
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