Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFPB |
Texto Completo: | https://repositorio.ufpb.br/jspui/handle/123456789/14119 |
Resumo: | Isatin and its derivatives have been presented in the literature with a broad pharmacological profile. Their Schiff bases, for example, present anticancer, antimicrobial and antiviral activities, so they are extensively explored in the literature. Based on this, this work was carried out with the objective of synthesizing and investigating the biological activity of some thiosemicarbazones derived from isatin. Of the ten thiosemicarbazones synthesized, six are unpublished in the literature and were obtained through the cheiosselective condensation reaction of thiosemicarbazide (9) with the ketonic portion of intermediates derived from isatin. These intermediates were obtained via nitration, chlorination and N-alkylation of the isatin. Six of these derivatives are homodimeric and were obtained in good yields (64-94%). The use of microwave irradiation (100 ° C) considerably reduced the reaction time of thiosemicarbazones compared to the methods described in the literature that make use of reflux and catalysis. The yields obtained were also quite satisfactory and ranged from 70 to 84%. Preliminary evaluation of the activity of thiosemicarbazones obtained and intermediates derived from isatin against strains of yeast bacteria and fungi was carried out. It was observed that thiosemicarbazones did not present antimicrobial biological activity, however, isatin and its nitrated and alil derivatives presented antimicrobial action (MIC = 128 to 512 μg.mL-1). The structural characterization of the compounds was performed by infrared (IR) spectroscopy and 1H and 13C NMR. |
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Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológicabases de SchiffTiossemicarbazonasMicro-ondasAtividade antimicrobianaSchiff basesThiosemicarbazonesMicrowaveAntimicrobial activityComposto orgânico - IsatinaTiossemicarbozonasCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIsatin and its derivatives have been presented in the literature with a broad pharmacological profile. Their Schiff bases, for example, present anticancer, antimicrobial and antiviral activities, so they are extensively explored in the literature. Based on this, this work was carried out with the objective of synthesizing and investigating the biological activity of some thiosemicarbazones derived from isatin. Of the ten thiosemicarbazones synthesized, six are unpublished in the literature and were obtained through the cheiosselective condensation reaction of thiosemicarbazide (9) with the ketonic portion of intermediates derived from isatin. These intermediates were obtained via nitration, chlorination and N-alkylation of the isatin. Six of these derivatives are homodimeric and were obtained in good yields (64-94%). The use of microwave irradiation (100 ° C) considerably reduced the reaction time of thiosemicarbazones compared to the methods described in the literature that make use of reflux and catalysis. The yields obtained were also quite satisfactory and ranged from 70 to 84%. Preliminary evaluation of the activity of thiosemicarbazones obtained and intermediates derived from isatin against strains of yeast bacteria and fungi was carried out. It was observed that thiosemicarbazones did not present antimicrobial biological activity, however, isatin and its nitrated and alil derivatives presented antimicrobial action (MIC = 128 to 512 μg.mL-1). The structural characterization of the compounds was performed by infrared (IR) spectroscopy and 1H and 13C NMR.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESA isatina e seus derivados vêm se apresentando na literatura com um amplo perfil farmacológico. Suas bases de Schiff, por exemplo, apresentam atividades anticâncer, antimicrobiana e antiviral, por isso são bastante exploradas na literatura. Com base nisso, este trabalho foi realizado com o objetivo de sintetizar e investigar a atividade biológica de algumas tiossemicarbazonas derivadas da isatina. Foram obtidas 10 tiossemicarbazonas, sendo 6 inéditas, através da reação de condensação quimiosseletiva da tiossemicarbazida (9) com a porção cetônica dos intermediários derivados da isatina. Estes intermediários foram obtidos via nitração, cloração e N-alquilação da isatina. Seis destes derivados são homodiméricos e foram obtidos em bons rendimentos (64-94%). O uso da irradiação de micro-ondas (100 °C) diminuiu consideravelmente o tempo de reação das tiossemicarbazonas em comparação com os métodos descritos na literatura que fazem o uso de refluxo e catálise. Os rendimentos obtidos também foram bastante satisfatórios e variaram de 70 a 84%. Foi realizada a avaliação preliminar da atividade antimicrobiana das tiossemicarbazonas obtidas e dos intermediários derivados da isatina contra cepas de bactérias e fungos leveduriformes. Foi observado que as tiossemicarbazonas não apresentaram atividade biológica antimicrobiana, no entanto a isatina e seus derivados nitrados e alilados apresentaram ação antimicrobiana (CIM = 128 a 512 µg.mL-1). A caracterização estrutural dos compostos foi realizada por espectroscopia de infravermelho (IV) e RMN de 1H e 13C.Universidade Federal da ParaíbaBrasilQuímicaPrograma de Pós-Graduação em QuímicaUFPBVasconcellos, Mário Luiz Araujo de Almeidahttp://lattes.cnpq.br/1010366111082767Lima Junior, Claudio Gabrielhttp://lattes.cnpq.br/5743384737397873Silva, Thaysa Suellen Mendonça da2019-05-02T12:09:47Z2018-11-142019-05-02T12:09:47Z2018-10-19info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesishttps://repositorio.ufpb.br/jspui/handle/123456789/14119porAttribution-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nd/3.0/br/info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFPBinstname:Universidade Federal da Paraíba (UFPB)instacron:UFPB2019-05-03T06:02:49Zoai:repositorio.ufpb.br:123456789/14119Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2019-05-03T06:02:49Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
title |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
spellingShingle |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica Silva, Thaysa Suellen Mendonça da bases de Schiff Tiossemicarbazonas Micro-ondas Atividade antimicrobiana Schiff bases Thiosemicarbazones Microwave Antimicrobial activity Composto orgânico - Isatina Tiossemicarbozonas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
title_full |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
title_fullStr |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
title_full_unstemmed |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
title_sort |
Síntese assistida por micro-ondas de tiossemicarbazonas derivadas da isatina com potencial atividade biológica |
author |
Silva, Thaysa Suellen Mendonça da |
author_facet |
Silva, Thaysa Suellen Mendonça da |
author_role |
author |
dc.contributor.none.fl_str_mv |
Vasconcellos, Mário Luiz Araujo de Almeida http://lattes.cnpq.br/1010366111082767 Lima Junior, Claudio Gabriel http://lattes.cnpq.br/5743384737397873 |
dc.contributor.author.fl_str_mv |
Silva, Thaysa Suellen Mendonça da |
dc.subject.por.fl_str_mv |
bases de Schiff Tiossemicarbazonas Micro-ondas Atividade antimicrobiana Schiff bases Thiosemicarbazones Microwave Antimicrobial activity Composto orgânico - Isatina Tiossemicarbozonas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
bases de Schiff Tiossemicarbazonas Micro-ondas Atividade antimicrobiana Schiff bases Thiosemicarbazones Microwave Antimicrobial activity Composto orgânico - Isatina Tiossemicarbozonas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Isatin and its derivatives have been presented in the literature with a broad pharmacological profile. Their Schiff bases, for example, present anticancer, antimicrobial and antiviral activities, so they are extensively explored in the literature. Based on this, this work was carried out with the objective of synthesizing and investigating the biological activity of some thiosemicarbazones derived from isatin. Of the ten thiosemicarbazones synthesized, six are unpublished in the literature and were obtained through the cheiosselective condensation reaction of thiosemicarbazide (9) with the ketonic portion of intermediates derived from isatin. These intermediates were obtained via nitration, chlorination and N-alkylation of the isatin. Six of these derivatives are homodimeric and were obtained in good yields (64-94%). The use of microwave irradiation (100 ° C) considerably reduced the reaction time of thiosemicarbazones compared to the methods described in the literature that make use of reflux and catalysis. The yields obtained were also quite satisfactory and ranged from 70 to 84%. Preliminary evaluation of the activity of thiosemicarbazones obtained and intermediates derived from isatin against strains of yeast bacteria and fungi was carried out. It was observed that thiosemicarbazones did not present antimicrobial biological activity, however, isatin and its nitrated and alil derivatives presented antimicrobial action (MIC = 128 to 512 μg.mL-1). The structural characterization of the compounds was performed by infrared (IR) spectroscopy and 1H and 13C NMR. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-11-14 2018-10-19 2019-05-02T12:09:47Z 2019-05-02T12:09:47Z |
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 |
https://repositorio.ufpb.br/jspui/handle/123456789/14119 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/14119 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Química Programa de Pós-Graduação em Química UFPB |
publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Química Programa de Pós-Graduação em Química UFPB |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFPB instname:Universidade Federal da Paraíba (UFPB) instacron:UFPB |
instname_str |
Universidade Federal da Paraíba (UFPB) |
instacron_str |
UFPB |
institution |
UFPB |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
collection |
Biblioteca Digital de Teses e Dissertações da UFPB |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB) |
repository.mail.fl_str_mv |
diretoria@ufpb.br|| diretoria@ufpb.br |
_version_ |
1801842946487615488 |