Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico
Ano de defesa: | 2016 |
---|---|
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
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/17962 |
Resumo: | This study shows the synthesis of five new 6-substituted 2-methylthio-4-pyrimidine carbohydrazides, aryl groups having such substituents (Ph, 4-FC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4) from the nucleophilic substitution of 6-substituted Ethyl 2-methylthiopyrimidine-4-carboxylate with hydrazine hydrochloride, with yields of 67- 78%. The cyclocondensation reactions of the carboidrazides, with 4-substituted 1,1,1-trifluorobut-3-en-2-ones led to the regioselective formation of twenty novel 3’- and 6-disubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydropyrazol-1-yl)(2-methylthiopyrimidin-4-yl) methanones, wherein the substituents on the pyrazoline (3') are Me, 2-furyl, Ph, 4-ClC6H4 and 4-MeOC6H4 in very good yields of 72-98%. The products obtained in this study were characterized by 1H and 13C NMR and low and high resolution mass spectrometry. The structure of representative compounds was confirmed by single crystal x-ray diffractometry. |
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network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2019-08-19T15:20:37Z2019-08-19T15:20:37Z2016-10-20http://repositorio.ufsm.br/handle/1/17962This study shows the synthesis of five new 6-substituted 2-methylthio-4-pyrimidine carbohydrazides, aryl groups having such substituents (Ph, 4-FC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4) from the nucleophilic substitution of 6-substituted Ethyl 2-methylthiopyrimidine-4-carboxylate with hydrazine hydrochloride, with yields of 67- 78%. The cyclocondensation reactions of the carboidrazides, with 4-substituted 1,1,1-trifluorobut-3-en-2-ones led to the regioselective formation of twenty novel 3’- and 6-disubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydropyrazol-1-yl)(2-methylthiopyrimidin-4-yl) methanones, wherein the substituents on the pyrazoline (3') are Me, 2-furyl, Ph, 4-ClC6H4 and 4-MeOC6H4 in very good yields of 72-98%. The products obtained in this study were characterized by 1H and 13C NMR and low and high resolution mass spectrometry. The structure of representative compounds was confirmed by single crystal x-ray diffractometry.Esse estudo apresenta a síntese uma série de cinco 2-metiltio-4-carbohidrazil-pirimidinas 6-substituídas inéditas, tendo como substituintes arílicos: Ph, 4-FC6H4, 4-BrC6H4, 4-MeC6H4 e 4-MeOC6H4, a partir da reação de substituição nucleofílica dos 2-metiltiopirimidina-4-carboxilatos de etila 6-substituídas com cloridrato de hidrazina, com rendimentos de 67-78%. As carbohidrazidas, através de reações de ciclocondensação com 1,1,1-trifluorobut-3-en-2-onas 4-substituídas, conduziram a formação regiosseletiva de uma série de vinte (5-hidróxi-5-(trifluormetil)-4,5-diidro-1H-pirazol-1-il)(2-metiltio-pirimidin-4-il)metanonas 3’- e 6- dissubstituídas inéditas, onde os substituintes na pirazolina (3’) são Me, 2-Furila, Ph, 4-ClC6H4 e 4-OMeC6H4 com rendimentos de 72 a 98%. Os produtos obtidos neste trabalho foram caracterizados por ressonância magnética nuclear de 1H e 13C e espectrometria de massas de baixa e alta resolução. A estrutura de compostos representativos foi confirmada por difração de raios-x em monocristal.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessPirimidinasPirazolHeterociclosTrifluormetilCiclocondensação regiosseletivaTuberculoseDoença de AlzheimerPyrimidinesPyrazoleHeterocyclesTrifluoromethylRegioselective cyclocondensationTuberculosisAlzheimer's diseaseCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológicoRegioselective synthesis of new (4,5-dihydropyrazol-1-yl)(pyrimidin-4-yl) methanones with pharmacological potentialinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Bencke, Carlos Eduardohttp://lattes.cnpq.br/1651914444296279Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980http://lattes.cnpq.br/3215982010548240Camargo, Adriano Felin100600000000600233dc1de-ab03-4f57-9b85-e40dc01a2d4f085f5202-352a-4525-bd35-02020baeb1bb2d75f64b-2c81-4a75-b9c3-45155a51a5b6e428c287-1542-4baf-bacc-c71aa65fc73areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2016_CAMARGO_ADRIANO.pdfDIS_PPGQUIMICA_2016_CAMARGO_ADRIANO.pdfDissertação de Mestradoapplication/pdf6688224http://repositorio.ufsm.br/bitstream/1/17962/1/DIS_PPGQUIMICA_2016_CAMARGO_ADRIANO.pdf6484bc2ebd004f0d77a7887bec7edc89MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
dc.title.alternative.eng.fl_str_mv |
Regioselective synthesis of new (4,5-dihydropyrazol-1-yl)(pyrimidin-4-yl) methanones with pharmacological potential |
title |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
spellingShingle |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico Camargo, Adriano Felin Pirimidinas Pirazol Heterociclos Trifluormetil Ciclocondensação regiosseletiva Tuberculose Doença de Alzheimer Pyrimidines Pyrazole Heterocycles Trifluoromethyl Regioselective cyclocondensation Tuberculosis Alzheimer's disease CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
title_full |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
title_fullStr |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
title_full_unstemmed |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
title_sort |
Síntese regiosseletiva de novas (4,5-diidropirazol-1-il)(-pirimidin-4-il)metanonas com potencial farmacológico |
author |
Camargo, Adriano Felin |
author_facet |
Camargo, Adriano Felin |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Bencke, Carlos Eduardo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/1651914444296279 |
dc.contributor.referee2.fl_str_mv |
Mostardeiro, Marco Aurelio |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6195396264565980 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3215982010548240 |
dc.contributor.author.fl_str_mv |
Camargo, Adriano Felin |
contributor_str_mv |
Zanatta, Nilo Bencke, Carlos Eduardo Mostardeiro, Marco Aurelio |
dc.subject.por.fl_str_mv |
Pirimidinas Pirazol Heterociclos Trifluormetil Ciclocondensação regiosseletiva Tuberculose Doença de Alzheimer |
topic |
Pirimidinas Pirazol Heterociclos Trifluormetil Ciclocondensação regiosseletiva Tuberculose Doença de Alzheimer Pyrimidines Pyrazole Heterocycles Trifluoromethyl Regioselective cyclocondensation Tuberculosis Alzheimer's disease CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Pyrimidines Pyrazole Heterocycles Trifluoromethyl Regioselective cyclocondensation Tuberculosis Alzheimer's disease |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This study shows the synthesis of five new 6-substituted 2-methylthio-4-pyrimidine carbohydrazides, aryl groups having such substituents (Ph, 4-FC6H4, 4-BrC6H4, 4-MeC6H4, 4-MeOC6H4) from the nucleophilic substitution of 6-substituted Ethyl 2-methylthiopyrimidine-4-carboxylate with hydrazine hydrochloride, with yields of 67- 78%. The cyclocondensation reactions of the carboidrazides, with 4-substituted 1,1,1-trifluorobut-3-en-2-ones led to the regioselective formation of twenty novel 3’- and 6-disubstituted (5-hydroxy-5-(trifluoromethyl)-4,5-dihydropyrazol-1-yl)(2-methylthiopyrimidin-4-yl) methanones, wherein the substituents on the pyrazoline (3') are Me, 2-furyl, Ph, 4-ClC6H4 and 4-MeOC6H4 in very good yields of 72-98%. The products obtained in this study were characterized by 1H and 13C NMR and low and high resolution mass spectrometry. The structure of representative compounds was confirmed by single crystal x-ray diffractometry. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-10-20 |
dc.date.accessioned.fl_str_mv |
2019-08-19T15:20:37Z |
dc.date.available.fl_str_mv |
2019-08-19T15:20:37Z |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/17962 |
url |
http://repositorio.ufsm.br/handle/1/17962 |
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 |
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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 |
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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 |
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