Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos
Ano de defesa: | 2011 |
---|---|
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/1/10512 |
Resumo: | This work describes an efficient approach for the regioselective synthesis of new series of substituted 1-(2-naphthoxyacetyl), 1-phenoxyacetyl, 1-thiophenoxyacetyl, 1-(N-phenylglicine)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles from the cyclocondensation reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3- en-2-ones [CF3C(O)CH=CHROMe(Et) where R = H, Me, Ph, 2-furyl, 1-naphthyl] with 2-aryloxyaceto, 2-thiophenoxyaceto, N-phenylglicine hidrazides under synthetic conventional procedures. These methodologies furnished high purity and air-stable products in 34 96 % yields. In a subsequent step, the reactions of dehydration intramolecular of two examples of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles, are described. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of substituted 1-(2-naphthoxyacetyl)- and 1-phenoxyacetyl-3-phenyl-5-trifluoromethyl-1H-pyrazoles in 82 and 78 % yields respectively. In addition, the series of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles were evaluated for antimicrobial activity. As the result, the 1-(N-phenylglicine)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol series showed the best activities where the concentrations greater or equal than 100 µg/mL inhibited the growth of tested bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), fungi(Candida albicans e Aspergillus fumigatus) and algae (Prototheca zopfii). Moreover, the test of antioxidant activity demonstrated that 5-trifluoromethyl- 5-hydroxy-4,5-dihydro-1H-pyrazoles non-substituted at position 3 of the pyrazoline ring, of each series, provided positive activity as trappers of the stable free radical DPPH by the qualitative 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC/MS) and their purity determined by CHNS Elemental Analysis. |
id |
UFSM_4b5aeb42c1b46311a996333f44402158 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/10512 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2017-05-152017-05-152011-07-01PITTALUGA, Everton Pedebos. Synthesis and antioxidant/antimicrobial activities of Substituted 1-naphthoxyacetyl-, 1-phenoxyacetyl-, 1-thiophenoxyacetyl- and 1-(n-phenylglicine)-5- Trifluoromethyl-5-hydroxy-4,5-dihydro-1h-pyrazoles. 2011. 154 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011.http://repositorio.ufsm.br/handle/1/10512This work describes an efficient approach for the regioselective synthesis of new series of substituted 1-(2-naphthoxyacetyl), 1-phenoxyacetyl, 1-thiophenoxyacetyl, 1-(N-phenylglicine)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles from the cyclocondensation reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3- en-2-ones [CF3C(O)CH=CHROMe(Et) where R = H, Me, Ph, 2-furyl, 1-naphthyl] with 2-aryloxyaceto, 2-thiophenoxyaceto, N-phenylglicine hidrazides under synthetic conventional procedures. These methodologies furnished high purity and air-stable products in 34 96 % yields. In a subsequent step, the reactions of dehydration intramolecular of two examples of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles, are described. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of substituted 1-(2-naphthoxyacetyl)- and 1-phenoxyacetyl-3-phenyl-5-trifluoromethyl-1H-pyrazoles in 82 and 78 % yields respectively. In addition, the series of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles were evaluated for antimicrobial activity. As the result, the 1-(N-phenylglicine)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol series showed the best activities where the concentrations greater or equal than 100 µg/mL inhibited the growth of tested bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), fungi(Candida albicans e Aspergillus fumigatus) and algae (Prototheca zopfii). Moreover, the test of antioxidant activity demonstrated that 5-trifluoromethyl- 5-hydroxy-4,5-dihydro-1H-pyrazoles non-substituted at position 3 of the pyrazoline ring, of each series, provided positive activity as trappers of the stable free radical DPPH by the qualitative 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC/MS) and their purity determined by CHNS Elemental Analysis.A presente dissertação descreve inicialmente a síntese regiosseletiva de séries inéditas de 5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazóis 1-(2-naftoxiacetil)-, 1-fenoxiacetil-, 1-tiofenoxiacetil- e 1-(N-fenilglicina) substituídos obtidos a partir de reações de condensação de 4-alcóxi-4-alquil(aril/heteroaril)-1,1,1-triflúor-3-alquen-2- onas [CF3C(O)CH=CROMe(Et), onde R = H, Me, Ph, 2-furil e 1-naftil] com 2-ariloxiaceto-, 2-tiofenoxiaceto- e N-fenilglicina hidrazidas, empregando métodos sintéticos convencionais. Estas metodologias conduziram a produtos puros e estáveis ao ar com rendimentos entre 34 e 96 %. Numa etapa subsequente são descritas as reações de desidratação intramolecular de 2 exemplares de 5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazóis 1-ariloxiacetil substituídos. Estas reações foram conduzidas em piridina/benzeno na presença de cloreto de tionila e possibilitaram o isolamento de 3-fenil-5-trifluormetil-1H-pirazóis 1-(2-naftoxiacetil)- e 1-fenoxiacetil substituídos com rendimentos de 82 e 78 %, respectivamente. Complementarmente, as séries das 5-trifluormetil-5-hidróxi-4,5-diidro-1Hpiraz óis foram avaliadas quanto à sua atividade antimicrobiana. Como resultado, a série de 1-(N-fenilglicina)-5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazóis apresentou as melhores atividades onde concentrações maiores ou iguais a 100 µg/mL inibiram o crescimento das bactérias (Staphylococcus aureus, Pseudomonas aeruginosa e Escherichia coli), fungos (Candida albicans e Aspergillus fumigatus) e alga (Prototheca zopfii) testados. Através do teste de atividade antioxidante, pelo método qualitativo que emprega o radical livre 2,2-difenil-1-picril-hidrazila (DPPH), observou-se de maneira geral que os 5-trifluormetil-5-hidróxi-4,5-diidro-1H-pirazóis não substituídos na posição 3 do anel pirazolínico, de cada série, apresentaram atividade positiva como trapeadores do radical livre estável DPPH. Os compostos inéditos sintetizados foram caracterizados por espectroscopia de RMN de 1H e 13C {1H}, cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e tiveram sua pureza determinada via análise elementar CHNS.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaVinil cetonas trifluormetiladasHidrazidas aril substituídasPirazolinasCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídosSynthesis and antioxidant/antimicrobial activities of Substituted 1-naphthoxyacetyl-, 1-phenoxyacetyl-, 1-thiophenoxyacetyl- and 1-(n-phenylglicine)-5- Trifluoromethyl-5-hydroxy-4,5-dihydro-1h-pyrazolesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Dornelles, Lucianohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9Zanatta, Nilohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4261325P3Pittaluga, Everton Pedebos10060000000040050050050050006c852ad-d805-43c3-99d6-93a6a86f507ce36593ac-be1c-47e5-9fc8-221ad7973ab47dfea8f7-fe97-4100-9d09-8f5a40fe23162f7bd6ce-78fa-4968-ac66-2d1407e90f60info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALPITTALUGA, EVERTON PEDEBOS.pdfapplication/pdf3549540http://repositorio.ufsm.br/bitstream/1/10512/1/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf59a072a18fd3cdeddfe5b76956f8fca8MD51TEXTPITTALUGA, EVERTON PEDEBOS.pdf.txtPITTALUGA, EVERTON PEDEBOS.pdf.txtExtracted texttext/plain192317http://repositorio.ufsm.br/bitstream/1/10512/2/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf.txtb83630f65dc426b8354ef86af382af53MD52THUMBNAILPITTALUGA, EVERTON PEDEBOS.pdf.jpgPITTALUGA, EVERTON PEDEBOS.pdf.jpgIM Thumbnailimage/jpeg5916http://repositorio.ufsm.br/bitstream/1/10512/3/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf.jpg83d5f9ec65d056f0e837bca9c96be86bMD531/105122017-07-25 12:03:46.629oai:repositorio.ufsm.br:1/10512Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:03:46Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
dc.title.alternative.eng.fl_str_mv |
Synthesis and antioxidant/antimicrobial activities of Substituted 1-naphthoxyacetyl-, 1-phenoxyacetyl-, 1-thiophenoxyacetyl- and 1-(n-phenylglicine)-5- Trifluoromethyl-5-hydroxy-4,5-dihydro-1h-pyrazoles |
title |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
spellingShingle |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos Pittaluga, Everton Pedebos Vinil cetonas trifluormetiladas Hidrazidas aril substituídas Pirazolinas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
title_full |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
title_fullStr |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
title_full_unstemmed |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
title_sort |
Síntese e atividades antimicrobiana/antioxidante de 5-trifluormetil-5-hidróxi-4,5-diidro-1h-pirazóis 1-(2-naftoxiacetil), 1-fenoxiacetil, 1-tiofenoxiacetil, 1-(n-fenilglicina) substituídos |
author |
Pittaluga, Everton Pedebos |
author_facet |
Pittaluga, Everton Pedebos |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 |
dc.contributor.referee1.fl_str_mv |
Dornelles, Luciano |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797177P9 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4261325P3 |
dc.contributor.author.fl_str_mv |
Pittaluga, Everton Pedebos |
contributor_str_mv |
Bonacorso, Helio Gauze Dornelles, Luciano Zanatta, Nilo |
dc.subject.por.fl_str_mv |
Vinil cetonas trifluormetiladas Hidrazidas aril substituídas Pirazolinas |
topic |
Vinil cetonas trifluormetiladas Hidrazidas aril substituídas Pirazolinas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes an efficient approach for the regioselective synthesis of new series of substituted 1-(2-naphthoxyacetyl), 1-phenoxyacetyl, 1-thiophenoxyacetyl, 1-(N-phenylglicine)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles from the cyclocondensation reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3- en-2-ones [CF3C(O)CH=CHROMe(Et) where R = H, Me, Ph, 2-furyl, 1-naphthyl] with 2-aryloxyaceto, 2-thiophenoxyaceto, N-phenylglicine hidrazides under synthetic conventional procedures. These methodologies furnished high purity and air-stable products in 34 96 % yields. In a subsequent step, the reactions of dehydration intramolecular of two examples of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles, are described. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of substituted 1-(2-naphthoxyacetyl)- and 1-phenoxyacetyl-3-phenyl-5-trifluoromethyl-1H-pyrazoles in 82 and 78 % yields respectively. In addition, the series of 5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles were evaluated for antimicrobial activity. As the result, the 1-(N-phenylglicine)-5- trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol series showed the best activities where the concentrations greater or equal than 100 µg/mL inhibited the growth of tested bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), fungi(Candida albicans e Aspergillus fumigatus) and algae (Prototheca zopfii). Moreover, the test of antioxidant activity demonstrated that 5-trifluoromethyl- 5-hydroxy-4,5-dihydro-1H-pyrazoles non-substituted at position 3 of the pyrazoline ring, of each series, provided positive activity as trappers of the stable free radical DPPH by the qualitative 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. The compounds were characterized by 1H and 13C {1H} NMR Spectroscopy, Gas Chromatography coupled to Mass Spectrometry (GC/MS) and their purity determined by CHNS Elemental Analysis. |
publishDate |
2011 |
dc.date.issued.fl_str_mv |
2011-07-01 |
dc.date.accessioned.fl_str_mv |
2017-05-15 |
dc.date.available.fl_str_mv |
2017-05-15 |
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 |
PITTALUGA, Everton Pedebos. Synthesis and antioxidant/antimicrobial activities of Substituted 1-naphthoxyacetyl-, 1-phenoxyacetyl-, 1-thiophenoxyacetyl- and 1-(n-phenylglicine)-5- Trifluoromethyl-5-hydroxy-4,5-dihydro-1h-pyrazoles. 2011. 154 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10512 |
identifier_str_mv |
PITTALUGA, Everton Pedebos. Synthesis and antioxidant/antimicrobial activities of Substituted 1-naphthoxyacetyl-, 1-phenoxyacetyl-, 1-thiophenoxyacetyl- and 1-(n-phenylglicine)-5- Trifluoromethyl-5-hydroxy-4,5-dihydro-1h-pyrazoles. 2011. 154 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011. |
url |
http://repositorio.ufsm.br/handle/1/10512 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
400 500 500 500 500 |
dc.relation.authority.fl_str_mv |
06c852ad-d805-43c3-99d6-93a6a86f507c e36593ac-be1c-47e5-9fc8-221ad7973ab4 7dfea8f7-fe97-4100-9d09-8f5a40fe2316 2f7bd6ce-78fa-4968-ac66-2d1407e90f60 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
BR |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/10512/1/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf http://repositorio.ufsm.br/bitstream/1/10512/2/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf.txt http://repositorio.ufsm.br/bitstream/1/10512/3/PITTALUGA%2c%20EVERTON%20PEDEBOS.pdf.jpg |
bitstream.checksum.fl_str_mv |
59a072a18fd3cdeddfe5b76956f8fca8 b83630f65dc426b8354ef86af382af53 83d5f9ec65d056f0e837bca9c96be86b |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793240077183221760 |