1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRPE |
Texto Completo: | http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7030 |
Resumo: | In this work, described the synthesis and characterization of new derivatives 3,5-substituted mono and bis 1,2,4-oxadiazoles and 2,3-unsaturated O and S-glycosides through Ferrier Rearrangement linked to 1,2,4-oxadiazole in the aglycone part. Performed initially the synthesis of the agents initial reactants: arylamidoximes (Ar = phenyl, o-toluil, m-toluil, p-toluil, p-bromophenyl, p-chlorophenyl, p-nitrophenyl) of isopropyl 3-mercaptopropionato, dimethyl malate and methyl salicylate, separately. The synthesis of the arylamidoximes 66a-g was carried out by the method described by Srivastava, from arylnitriles 38a-g with hydroxylamine hydrochloride and sodium carbonate.The products 64a-g were obtained with moderate and high yields (30 - 97%). The isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate were obtained through esterification reaction of salicylic acid, 3-mercapto propionic acid and Malic acid respectively, with the corresponding alcohols using sulfuric acid as a catalyst, which they were obtained satisfactory yields of 60%, 79% and 78%, respectively. The mono and bis 1,2,4-oxadiazoles 70a-d, 73a-d, 74a-d, e 77a-e were synthesized by treatment of arylamidoximes 66a-g with isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate, using two different methods: use of microwave irradiation in the presence of potassium carbonate for the synthesis of mono-1,2,4-oxadiazoles and heating in the absence of solvent and base for the synthesis of bis-1,2,4 -oxadiazoles. The heterocyclic 70a-d, 73a-d, 74a-d and 77a-d were obtained in moderate yields (20-91%). The glycosides were obtained by reacting the tri-O-acetyl-D-glucal (78) with the different alcohols, in the presence of montimorillonit as a catalyst. The antitumor and antimicrobial activities of the synthesized compounds were evaluated.The structures of the compounds obtained were elucidated by spectroscopic methods Infrared and nuclear magnetic resonance 1H and 13C and also by high resolution mass. |
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FREITAS FILHO, João Rufino deFREITAS, Juliano Carlos Rufino deRAMOS, Clécio SouzaFREITAS, Jucleiton José Rufino dehttp://lattes.cnpq.br/6283508919043192MATA, Mauricélia Maria de Sousa2017-07-31T13:13:10Z2017-02-23MATA, Mauricélia Maria de Sousa. 1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural. 2017. 94 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife.http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7030In this work, described the synthesis and characterization of new derivatives 3,5-substituted mono and bis 1,2,4-oxadiazoles and 2,3-unsaturated O and S-glycosides through Ferrier Rearrangement linked to 1,2,4-oxadiazole in the aglycone part. Performed initially the synthesis of the agents initial reactants: arylamidoximes (Ar = phenyl, o-toluil, m-toluil, p-toluil, p-bromophenyl, p-chlorophenyl, p-nitrophenyl) of isopropyl 3-mercaptopropionato, dimethyl malate and methyl salicylate, separately. The synthesis of the arylamidoximes 66a-g was carried out by the method described by Srivastava, from arylnitriles 38a-g with hydroxylamine hydrochloride and sodium carbonate.The products 64a-g were obtained with moderate and high yields (30 - 97%). The isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate were obtained through esterification reaction of salicylic acid, 3-mercapto propionic acid and Malic acid respectively, with the corresponding alcohols using sulfuric acid as a catalyst, which they were obtained satisfactory yields of 60%, 79% and 78%, respectively. The mono and bis 1,2,4-oxadiazoles 70a-d, 73a-d, 74a-d, e 77a-e were synthesized by treatment of arylamidoximes 66a-g with isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate, using two different methods: use of microwave irradiation in the presence of potassium carbonate for the synthesis of mono-1,2,4-oxadiazoles and heating in the absence of solvent and base for the synthesis of bis-1,2,4 -oxadiazoles. The heterocyclic 70a-d, 73a-d, 74a-d and 77a-d were obtained in moderate yields (20-91%). The glycosides were obtained by reacting the tri-O-acetyl-D-glucal (78) with the different alcohols, in the presence of montimorillonit as a catalyst. The antitumor and antimicrobial activities of the synthesized compounds were evaluated.The structures of the compounds obtained were elucidated by spectroscopic methods Infrared and nuclear magnetic resonance 1H and 13C and also by high resolution mass.Neste trabalho, foi descrito a síntese e caracterização de novos mono e bis 1,2,4-oxadiazóis-3,5-dissubistutido, e novos O e S-glicosídeos 2,3-insaturados através do Rearranjo de Ferrier ligado ao 1,2,4-oxadiazol na parte aglicônica. Realizou inicialmente a síntese dos compostos de partidas: arilamidoximas ( fenil, o-toluil, m-toluil, p-toluil, p-bromofenil, p-clorofenil, p-nitrofenil), 3-mercaptopropionato de isopropila, malato de dimetila e salicilato de metila, separadamente. A síntese das arilamidoximas 66a-g foi realizada através do método descrito por Srivastava, a partir das arilnitrilas 64a-e com cloridrato de hidroxalamina e carbonato de sódio. Os produtos 66a-g foram obtidos com rendimentos moderados e bons (30% - 97%). O malato de dimetila, 3-mercaptopropionato de isopropila e salicilato de metila, foram obtidos através da reação de esterificação do ácido salicílico, ácido 3-mercapto propiônico e ácido málico respectivamente, com os correspondentes alcoóis utilizando o ácido sulfúrico como catalisador, onde foram obtidos rendimentos satisfatórios de 60%, 79% e 78%, respectivamente. Os monos e bis-1,2,4-oxadiazóis 70a-d, 73a-d, 74a-d, e 77a-e foram sintetizados pela reação das arilamidoximas 66a-e com o malato de dimetila, o 3-mercaptopropionato de isopropila e o salicilato de metila, separadamente, utilizando dois métodos diferentes: uso de irradiação de micro-ondas na presença de carbonato de potássio para a síntese de 1,2,4-oxadiazóis e aquecimento na ausência de solvente e base para a síntese dos bis-1,2,4-oxadiazóis. Os heterocíclicos 70a-d, 73a-d, 74a-d e 77a-e foram obtidos com rendimentos moderados (20-91%). Os glicosídeos foram obtidos reagindo o tri-O-acetil-D-glical (79) com os diferentes álcoois, em presença de montimorillonita como catalisador. Foram avaliado as atividades antitumoral e antimicrobiana dos compostos sintetizados. As estruturas dos compostos obtidos foram elucidadas por métodos espectroscópicos de Infravermelho e Ressonância Magnética Nuclear de 1H e 13C e também por massa de alta resolução.Submitted by Mario BC (mario@bc.ufrpe.br) on 2017-07-31T13:13:10Z No. of bitstreams: 1 Mauricelia Maria de Sousa Mata.pdf: 2984908 bytes, checksum: 1b8b4b484714932a47152e617d4b2f81 (MD5)Made available in DSpace on 2017-07-31T13:13:10Z (GMT). No. of bitstreams: 1 Mauricelia Maria de Sousa Mata.pdf: 2984908 bytes, checksum: 1b8b4b484714932a47152e617d4b2f81 (MD5) Previous issue date: 2017-02-23Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESapplication/pdfporUniversidade Federal Rural de PernambucoPrograma de Pós-Graduação em QuímicaUFRPEBrasilDepartamento de QuímicaOxadiazolGlicosídeoArilamidoximaCIENCIAS EXATAS E DA TERRA::QUIMICA1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estruturalinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis1435648362225100898600600600600380641605545709103015717003253031171952075167498588264571info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRPEinstname:Universidade Federal Rural de Pernambuco (UFRPE)instacron:UFRPELICENSElicense.txtlicense.txttext/plain; charset=utf-82165http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7030/1/license.txtbd3efa91386c1718a7f26a329fdcb468MD51ORIGINALMauricelia Maria de Sousa Mata.pdfMauricelia Maria de Sousa Mata.pdfapplication/pdf2984908http://www.tede2.ufrpe.br:8080/tede2/bitstream/tede2/7030/2/Mauricelia+Maria+de+Sousa+Mata.pdf1b8b4b484714932a47152e617d4b2f81MD52tede2/70302018-06-19 11:43:51.281oai:tede2: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Biblioteca Digital de Teses e Dissertaçõeshttp://www.tede2.ufrpe.br:8080/tede/PUBhttp://www.tede2.ufrpe.br:8080/oai/requestbdtd@ufrpe.br ||bdtd@ufrpe.bropendoar:2024-05-28T12:35:06.937475Biblioteca Digital de Teses e Dissertações da UFRPE - Universidade Federal Rural de Pernambuco (UFRPE)false |
dc.title.por.fl_str_mv |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
title |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
spellingShingle |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural MATA, Mauricélia Maria de Sousa Oxadiazol Glicosídeo Arilamidoxima CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
title_full |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
title_fullStr |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
title_full_unstemmed |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
title_sort |
1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural |
author |
MATA, Mauricélia Maria de Sousa |
author_facet |
MATA, Mauricélia Maria de Sousa |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
FREITAS FILHO, João Rufino de |
dc.contributor.advisor-co1.fl_str_mv |
FREITAS, Juliano Carlos Rufino de |
dc.contributor.referee1.fl_str_mv |
RAMOS, Clécio Souza |
dc.contributor.referee2.fl_str_mv |
FREITAS, Jucleiton José Rufino de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6283508919043192 |
dc.contributor.author.fl_str_mv |
MATA, Mauricélia Maria de Sousa |
contributor_str_mv |
FREITAS FILHO, João Rufino de FREITAS, Juliano Carlos Rufino de RAMOS, Clécio Souza FREITAS, Jucleiton José Rufino de |
dc.subject.por.fl_str_mv |
Oxadiazol Glicosídeo Arilamidoxima |
topic |
Oxadiazol Glicosídeo Arilamidoxima CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, described the synthesis and characterization of new derivatives 3,5-substituted mono and bis 1,2,4-oxadiazoles and 2,3-unsaturated O and S-glycosides through Ferrier Rearrangement linked to 1,2,4-oxadiazole in the aglycone part. Performed initially the synthesis of the agents initial reactants: arylamidoximes (Ar = phenyl, o-toluil, m-toluil, p-toluil, p-bromophenyl, p-chlorophenyl, p-nitrophenyl) of isopropyl 3-mercaptopropionato, dimethyl malate and methyl salicylate, separately. The synthesis of the arylamidoximes 66a-g was carried out by the method described by Srivastava, from arylnitriles 38a-g with hydroxylamine hydrochloride and sodium carbonate.The products 64a-g were obtained with moderate and high yields (30 - 97%). The isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate were obtained through esterification reaction of salicylic acid, 3-mercapto propionic acid and Malic acid respectively, with the corresponding alcohols using sulfuric acid as a catalyst, which they were obtained satisfactory yields of 60%, 79% and 78%, respectively. The mono and bis 1,2,4-oxadiazoles 70a-d, 73a-d, 74a-d, e 77a-e were synthesized by treatment of arylamidoximes 66a-g with isopropyl 3-mercaptopropionate, dimethyl malate and methyl salicylate, using two different methods: use of microwave irradiation in the presence of potassium carbonate for the synthesis of mono-1,2,4-oxadiazoles and heating in the absence of solvent and base for the synthesis of bis-1,2,4 -oxadiazoles. The heterocyclic 70a-d, 73a-d, 74a-d and 77a-d were obtained in moderate yields (20-91%). The glycosides were obtained by reacting the tri-O-acetyl-D-glucal (78) with the different alcohols, in the presence of montimorillonit as a catalyst. The antitumor and antimicrobial activities of the synthesized compounds were evaluated.The structures of the compounds obtained were elucidated by spectroscopic methods Infrared and nuclear magnetic resonance 1H and 13C and also by high resolution mass. |
publishDate |
2017 |
dc.date.accessioned.fl_str_mv |
2017-07-31T13:13:10Z |
dc.date.issued.fl_str_mv |
2017-02-23 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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masterThesis |
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publishedVersion |
dc.identifier.citation.fl_str_mv |
MATA, Mauricélia Maria de Sousa. 1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural. 2017. 94 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
dc.identifier.uri.fl_str_mv |
http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7030 |
identifier_str_mv |
MATA, Mauricélia Maria de Sousa. 1,2,4-oxadiazóis e O e S-glicosídeos-2,3-insaturados : síntese e caracterização estrutural. 2017. 94 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural de Pernambuco, Recife. |
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http://www.tede2.ufrpe.br:8080/tede2/handle/tede2/7030 |
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Universidade Federal Rural de Pernambuco |
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Universidade Federal Rural de Pernambuco |
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