5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis
Ano de defesa: | 2008 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10434 |
Resumo: | This work describes the synthesis of series of 5-hydroxy-3-[alkyl(aryl/heteroaryl)]-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1(carbonylpyridyl)pyrazoles, obtained from the reactions of 1,1,1-trihalo-4-[alkyl(aryl/heteroaryl)]-4-alkoxy-3-alken-2-ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Ph, 4-ClPh, 4-BrPh, 4-FPh, 4-MePh, 2-Furyl, 2-Thienyl and X= F, Cl] with hidrazines (NH2NHC(O)Z), where Z = 4-pyridyl, 2-chloro-4-pyridyl and 3-pyridyl, in good yields (50-89%). The obtained compounds were evaluated for their in vitro biological activities against Mycobacterium tuberculosis ATCC 27294 (H37Rv) strains, where it was found that trifluoromethylated compounds were more active than their trichloromethylated analogues. Moreover, the position of the atom of nitrogen and the chloro substituent in the ring of pyridine influences the activity of these compounds. The synthesised pyrazoles with substituints R1= H and X=F (3a) and R1=4-MePh and X=F (3g) showed the best activity against the tested strains above mentioned. The compounds were characterized by analytical 1H and 13C NMR and of Mass Spectrometry (GC-MS), and its purities they were determined by Elementary analysis analysis. |
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2017-05-182017-05-182008-08-06NAVARINI, Jussara. 5-trihalomethyl-4,5-dihydro-1h-1-(carbonylpyridyl) pyrazoles: synthesis and biological activity against Mycobacterium tuberculosis. 2008. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008.http://repositorio.ufsm.br/handle/1/10434This work describes the synthesis of series of 5-hydroxy-3-[alkyl(aryl/heteroaryl)]-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1(carbonylpyridyl)pyrazoles, obtained from the reactions of 1,1,1-trihalo-4-[alkyl(aryl/heteroaryl)]-4-alkoxy-3-alken-2-ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Ph, 4-ClPh, 4-BrPh, 4-FPh, 4-MePh, 2-Furyl, 2-Thienyl and X= F, Cl] with hidrazines (NH2NHC(O)Z), where Z = 4-pyridyl, 2-chloro-4-pyridyl and 3-pyridyl, in good yields (50-89%). The obtained compounds were evaluated for their in vitro biological activities against Mycobacterium tuberculosis ATCC 27294 (H37Rv) strains, where it was found that trifluoromethylated compounds were more active than their trichloromethylated analogues. Moreover, the position of the atom of nitrogen and the chloro substituent in the ring of pyridine influences the activity of these compounds. The synthesised pyrazoles with substituints R1= H and X=F (3a) and R1=4-MePh and X=F (3g) showed the best activity against the tested strains above mentioned. The compounds were characterized by analytical 1H and 13C NMR and of Mass Spectrometry (GC-MS), and its purities they were determined by Elementary analysis analysis.O presente trabalho descreve a síntese de séries de 5-hidroxi-3-alquil(aril/heteroaril)-5-trifluor[cloro]metil-4,5-diidro-1H-1-(carbonilpiridil)pirazóis, obtidas a partir de reações de 1,1,1-trialo-4-alquil(aril/heteroaril)-4-alcoxi-3-alquen-2-onas [CX3C(O)CH=CR1OR, onde R = Me, Et; R1 = H, Ph, 4-ClPh, 4-BrPh, 4-FPh, 4-MePh, 2-Furil e 2-tienil e X = F, Cl] com hidrazinas (NH2NHC(O)Z, onde Z = 4-piridil, 2-cloro-4-piridil e 3-piridil), em bons rendimentos ( 50-89%). Os compostos sintetizados foram avaliados quanto à atividade biológica in vitro frente ao de Mycobacterium tuberculosis ATCC 27294(H37Rv), onde verificou-se que compostos trifluormetilados são mais ativos que seus análogos triclorometilados. Além disso, a posição do átomo de nitrogênio e o substituinte cloro no anel piridínico influenciaram na atividade destes compostos. Os pirazóis sintetizados com substituintes R1= H e X=F (3a) e R1= 4-MePh e X=F (3g) apresentaram melhor ativade contra as cepas testadas, mencionadas acima. Os compostos foram caracterizados a partir dos dados de RMN de 1H, RMN de 13C {1H} e por Espectrometria de Massas, e sua pureza comprovada por Análise Elementar.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaSíntese químicaTuberculosePirazóisCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis5-trihalomethyl-4,5-dihydro-1h-1-(carbonylpyridyl) pyrazoles: synthesis and biological activity against Mycobacterium tuberculosisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Alves, Sydney Hartzhttp://lattes.cnpq.br/0330782478769631Flores, Alex Fabiani Clarohttp://lattes.cnpq.br/1159954352174167http://lattes.cnpq.br/4769427023889148Navarini, Jussara10060000000040050050050050006c852ad-d805-43c3-99d6-93a6a86f507cb2f5a0e3-a336-4863-940b-4874569e988d7928080e-16be-47fd-b0a3-6d394fcd82a717a00027-8984-4561-9228-46697f540c2binfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALJUSSARANAVARINI.pdfapplication/pdf1227205http://repositorio.ufsm.br/bitstream/1/10434/1/JUSSARANAVARINI.pdf5da5916f5fc6297bd8e827a4d4c83e51MD51TEXTJUSSARANAVARINI.pdf.txtJUSSARANAVARINI.pdf.txtExtracted texttext/plain138747http://repositorio.ufsm.br/bitstream/1/10434/2/JUSSARANAVARINI.pdf.txtf63c4d50554b5f47ce11746202f507e7MD52THUMBNAILJUSSARANAVARINI.pdf.jpgJUSSARANAVARINI.pdf.jpgIM Thumbnailimage/jpeg5016http://repositorio.ufsm.br/bitstream/1/10434/3/JUSSARANAVARINI.pdf.jpg50585b5342bdd170b9323b6bf23fb2edMD531/104342022-07-21 15:06:11.19oai:repositorio.ufsm.br:1/10434Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132022-07-21T18:06:11Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
dc.title.alternative.eng.fl_str_mv |
5-trihalomethyl-4,5-dihydro-1h-1-(carbonylpyridyl) pyrazoles: synthesis and biological activity against Mycobacterium tuberculosis |
title |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
spellingShingle |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis Navarini, Jussara Química Síntese química Tuberculose Pirazóis CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
title_full |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
title_fullStr |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
title_full_unstemmed |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
title_sort |
5-trialometil-4,5-diidro-1h-1-(carbonilpiridil)pirazóis: síntese e atividade biológica frente ao Mycobacterium tuberculosis |
author |
Navarini, Jussara |
author_facet |
Navarini, Jussara |
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 |
Alves, Sydney Hartz |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0330782478769631 |
dc.contributor.referee2.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/1159954352174167 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4769427023889148 |
dc.contributor.author.fl_str_mv |
Navarini, Jussara |
contributor_str_mv |
Bonacorso, Helio Gauze Alves, Sydney Hartz Flores, Alex Fabiani Claro |
dc.subject.por.fl_str_mv |
Química Síntese química Tuberculose Pirazóis |
topic |
Química Síntese química Tuberculose Pirazóis CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis of series of 5-hydroxy-3-[alkyl(aryl/heteroaryl)]-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1(carbonylpyridyl)pyrazoles, obtained from the reactions of 1,1,1-trihalo-4-[alkyl(aryl/heteroaryl)]-4-alkoxy-3-alken-2-ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Ph, 4-ClPh, 4-BrPh, 4-FPh, 4-MePh, 2-Furyl, 2-Thienyl and X= F, Cl] with hidrazines (NH2NHC(O)Z), where Z = 4-pyridyl, 2-chloro-4-pyridyl and 3-pyridyl, in good yields (50-89%). The obtained compounds were evaluated for their in vitro biological activities against Mycobacterium tuberculosis ATCC 27294 (H37Rv) strains, where it was found that trifluoromethylated compounds were more active than their trichloromethylated analogues. Moreover, the position of the atom of nitrogen and the chloro substituent in the ring of pyridine influences the activity of these compounds. The synthesised pyrazoles with substituints R1= H and X=F (3a) and R1=4-MePh and X=F (3g) showed the best activity against the tested strains above mentioned. The compounds were characterized by analytical 1H and 13C NMR and of Mass Spectrometry (GC-MS), and its purities they were determined by Elementary analysis analysis. |
publishDate |
2008 |
dc.date.issued.fl_str_mv |
2008-08-06 |
dc.date.accessioned.fl_str_mv |
2017-05-18 |
dc.date.available.fl_str_mv |
2017-05-18 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
NAVARINI, Jussara. 5-trihalomethyl-4,5-dihydro-1h-1-(carbonylpyridyl) pyrazoles: synthesis and biological activity against Mycobacterium tuberculosis. 2008. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10434 |
identifier_str_mv |
NAVARINI, Jussara. 5-trihalomethyl-4,5-dihydro-1h-1-(carbonylpyridyl) pyrazoles: synthesis and biological activity against Mycobacterium tuberculosis. 2008. 121 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
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http://repositorio.ufsm.br/handle/1/10434 |
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por |
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