Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas
Ano de defesa: | 2016 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
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Departamento: |
Química
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País: |
Brasil
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Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/17964 |
Resumo: | This 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. |
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oai_identifier_str |
oai:repositorio.ufsm.br:1/17964 |
network_acronym_str |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2019-08-19T18:08:59Z2019-08-19T18:08:59Z2016-03-28http://repositorio.ufsm.br/handle/1/17964This 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.Este 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.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccess1,1,1-trifluor-4-metóxi-3-alquen-2-ona1H-pirazol-1-(tio)carboxamidaPirazoliltiazóisHidrazidas graxas1,1,1-trifluoro-4-methyl-3-alquen-2-one1H-pyrazol-1-(thio) carboxamidePyrazol-1-yl thiazolesFatty hidrazidesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longasSynthesis, characterization and evaluation antimicrobial of new heterocycles nitrogenous using as precursors Β- -alkoxyvinyl trifluoromethyl ketone chains alkyl longinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisFlores, Alex Fabiani Clarohttp://lattes.cnpq.br/1159954352174167Fernandes, Liana da Silvahttp://lattes.cnpq.br/0573570242395130Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Fantinel, Leonardohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4777461U9Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980http://lattes.cnpq.br/0395675025653002Mello, Débora Lombe de1006000000006008a4555ae-c246-4b1a-adac-bf3b2784da0870386445-7f10-464a-be01-fc2355abd7f7382563b5-0585-486b-a7a3-07dcac36dcc9f0970438-aab7-4bbe-8d26-13140ae7303aeba5e7a6-11ae-4c8d-8467-992f3d7d46e63aba656a-1abe-40b3-a6cb-05c237a2c77ereponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2016_MELLO_DEBORA.pdfTES_PPGQUIMICA_2016_MELLO_DEBORA.pdfTese de Doutoradoapplication/pdf7046249http://repositorio.ufsm.br/bitstream/1/17964/1/TES_PPGQUIMICA_2016_MELLO_DEBORA.pdf42811eea3b317857c7af6df09fbe72d8MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
dc.title.alternative.eng.fl_str_mv |
Synthesis, characterization and evaluation antimicrobial of new heterocycles nitrogenous using as precursors Β- -alkoxyvinyl trifluoromethyl ketone chains alkyl long |
title |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
spellingShingle |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas Mello, Débora Lombe de 1,1,1-trifluor-4-metóxi-3-alquen-2-ona 1H-pirazol-1-(tio)carboxamida Pirazoliltiazóis Hidrazidas graxas 1,1,1-trifluoro-4-methyl-3-alquen-2-one 1H-pyrazol-1-(thio) carboxamide Pyrazol-1-yl thiazoles Fatty hidrazides CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
title_full |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
title_fullStr |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
title_full_unstemmed |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
title_sort |
Síntese, caracterização e avaliação antimicrobiana de novos heterociclos nitrogenados utilizando como precursores β-alcóxivinil trifluormetil cetonas de cadeias alquílicas longas |
author |
Mello, Débora Lombe de |
author_facet |
Mello, Débora Lombe de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/1159954352174167 |
dc.contributor.referee1.fl_str_mv |
Fernandes, Liana da Silva |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0573570242395130 |
dc.contributor.referee2.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee3.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee3Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4777461U9 |
dc.contributor.referee4.fl_str_mv |
Mostardeiro, Marco Aurelio |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/6195396264565980 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0395675025653002 |
dc.contributor.author.fl_str_mv |
Mello, Débora Lombe de |
contributor_str_mv |
Flores, Alex Fabiani Claro Fernandes, Liana da Silva Rodrigues, Oscar Endrigo Dorneles Fantinel, Leonardo Mostardeiro, Marco Aurelio |
dc.subject.por.fl_str_mv |
1,1,1-trifluor-4-metóxi-3-alquen-2-ona 1H-pirazol-1-(tio)carboxamida Pirazoliltiazóis Hidrazidas graxas |
topic |
1,1,1-trifluor-4-metóxi-3-alquen-2-ona 1H-pirazol-1-(tio)carboxamida Pirazoliltiazóis Hidrazidas graxas 1,1,1-trifluoro-4-methyl-3-alquen-2-one 1H-pyrazol-1-(thio) carboxamide Pyrazol-1-yl thiazoles Fatty hidrazides CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
1,1,1-trifluoro-4-methyl-3-alquen-2-one 1H-pyrazol-1-(thio) carboxamide Pyrazol-1-yl thiazoles Fatty hidrazides |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This 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. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-03-28 |
dc.date.accessioned.fl_str_mv |
2019-08-19T18:08:59Z |
dc.date.available.fl_str_mv |
2019-08-19T18:08:59Z |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/17964 |
url |
http://repositorio.ufsm.br/handle/1/17964 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
8a4555ae-c246-4b1a-adac-bf3b2784da08 70386445-7f10-464a-be01-fc2355abd7f7 382563b5-0585-486b-a7a3-07dcac36dcc9 f0970438-aab7-4bbe-8d26-13140ae7303a eba5e7a6-11ae-4c8d-8467-992f3d7d46e6 3aba656a-1abe-40b3-a6cb-05c237a2c77e |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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 |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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/1/17964/1/TES_PPGQUIMICA_2016_MELLO_DEBORA.pdf http://repositorio.ufsm.br/bitstream/1/17964/2/license_rdf http://repositorio.ufsm.br/bitstream/1/17964/3/license.txt http://repositorio.ufsm.br/bitstream/1/17964/4/TES_PPGQUIMICA_2016_MELLO_DEBORA.pdf.txt http://repositorio.ufsm.br/bitstream/1/17964/5/TES_PPGQUIMICA_2016_MELLO_DEBORA.pdf.jpg |
bitstream.checksum.fl_str_mv |
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bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 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_ |
1793240130683666432 |