Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana
Ano de defesa: | 2020 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal da Paraíba
Brasil Química Programa de Pós-Graduação em Química UFPB |
Programa de Pós-Graduação: |
Não Informado pela instituição
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Departamento: |
Não Informado pela instituição
|
País: |
Não Informado pela instituição
|
Palavras-chave em Português: | |
Link de acesso: | https://repositorio.ufpb.br/jspui/handle/123456789/19954 |
Resumo: | The indole nucleus, contained in isatin, is present in several bioactive molecules and this makes isatin an excellent synthetic block for the development of new potentially active compounds. Isatin derivatives are commonly reported in the literature with different biological activities and thiosemicarbazones stand out for their synthetic simplicity and high biological potential. Thus, this work aimed of analogous series synthesis of β-phenyl thiosemicarbazones derived from isatin by irradiation of microwave and investigation of antibacterial activity. Among these compounds, eight are unpublished. Preliminary experiments were carried out by varying the parameters of catalysis, temperature and reaction time in order to define a general method of synthesis to obtain the compounds. Isatin derivatives were prepared and used as intermediates in the synthesis of thiosemicarbazones. The series of β-thiophenylsemicarbazones was obtained in reactions assisted by microwave radiation, lasting 10 min in the presence of acetic acid as a catalyst. The yields obtained varied from 50-94% and were compared with those presented in the literature. All compounds were characterized by 13C and 1H NMR spectroscopy. The method developed for the synthesis of these compounds in microwave reactor proved to be a useful and efficient to obtain the products in a short reaction time. The in silico study was carried out and indicated that the compounds are in compliance with the rule of Lipinski and ADME, presenting a satisfactory oral bioavailability. The compounds were evaluated for antibacterial activity in the strains of S. aureus, E. coli and P. aeruginosa and thiosemicarbazone derived from 5-chloro-1-methyl-isatin (64) was the only one capable of inhibiting the growth of microorganisms with MIC of 562.5 μg / mL, indicating strong inhibitory activity. |
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Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacterianaTiossemicarbazonasβ-tiofenilsemicarbazonasAtividade antibacterianaDerivados de isatinaSíntese em micro-ondasThiosemicarbazonesβ-phenylthiosemicarbazonesAntibacterial activityIsatin derivativesMicrowave synthesisCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThe indole nucleus, contained in isatin, is present in several bioactive molecules and this makes isatin an excellent synthetic block for the development of new potentially active compounds. Isatin derivatives are commonly reported in the literature with different biological activities and thiosemicarbazones stand out for their synthetic simplicity and high biological potential. Thus, this work aimed of analogous series synthesis of β-phenyl thiosemicarbazones derived from isatin by irradiation of microwave and investigation of antibacterial activity. Among these compounds, eight are unpublished. Preliminary experiments were carried out by varying the parameters of catalysis, temperature and reaction time in order to define a general method of synthesis to obtain the compounds. Isatin derivatives were prepared and used as intermediates in the synthesis of thiosemicarbazones. The series of β-thiophenylsemicarbazones was obtained in reactions assisted by microwave radiation, lasting 10 min in the presence of acetic acid as a catalyst. The yields obtained varied from 50-94% and were compared with those presented in the literature. All compounds were characterized by 13C and 1H NMR spectroscopy. The method developed for the synthesis of these compounds in microwave reactor proved to be a useful and efficient to obtain the products in a short reaction time. The in silico study was carried out and indicated that the compounds are in compliance with the rule of Lipinski and ADME, presenting a satisfactory oral bioavailability. The compounds were evaluated for antibacterial activity in the strains of S. aureus, E. coli and P. aeruginosa and thiosemicarbazone derived from 5-chloro-1-methyl-isatin (64) was the only one capable of inhibiting the growth of microorganisms with MIC of 562.5 μg / mL, indicating strong inhibitory activity.NenhumaO núcleo indol, contido na isatina, está presente em várias moléculas bioativas e isso faz da isatina um excelente bloco sintético para o desenvolvimento de novos compostos potencialmente ativos. Derivados de isatina são comumente reportados na literatura com diferentes atividades biológicas e as tiossemicarbazonas se destacam pela simplicidade sintética e o alto potencial biológico. Desta forma, este trabalho teve como objetivo a síntese de uma série análoga de quinze β-feniltiossemicarbazonas derivadas de isatina via irradiação de micro-ondas e a investigação da atividade antibacteriana. Entre estes compostos, oito são inéditos. Experimentos preliminares foram realizados variando-se parâmetros de catálise, temperatura e tempo reacional, com a finalidade de definir um método geral de síntese para obtenção dos compostos. Derivados de isatina foram previamente preparados e utilizados como intermediários na síntese das tiossemicarbazonas. A série de β-tiofenilsemicarbazonas foi obtida por meio de reações assistidas por radiação de micro-ondas, com duração de 10 min na presença ácido acético como catalizador. Os rendimentos obtidos variaram de 50-94% e foram comparados com os apresentados na literatura. Todos os compostos foram caracterizados por espectroscopia de RMN de 1H e 13C. O método desenvolvido para síntese desses compostos em reator de micro-ondas se mostrou útil e eficiente para obtenção dos produtos em um curto tempo de reação. O estudo in silico foi realizado e indicou que os compostos estão em conformidade com a regra de Lipinski e ADME, apresentando uma satisfatória biodisponibilidade oral. Os compostos foram avaliados quanto à atividade antibacteriana para as cepas de S. aureus, E. coli e P. aeruginosa. A tiossemicarbazona derivada da 5-cloro-1-metil-isatina (64) foi o único composto capaz de inibir o crescimento dos microrganismos com CIM de 562,5 μg/mL, indicando forte atividade inibitória.Universidade Federal da ParaíbaBrasilQuímicaPrograma de Pós-Graduação em QuímicaUFPBLima Junior, Claudio Gabrielhttp://lattes.cnpq.br/5743384737397873Silva, Everton da Paz2021-04-15T19:40:53Z2020-03-122021-04-15T19:40:53Z2020-03-09info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesishttps://repositorio.ufpb.br/jspui/handle/123456789/19954porhttp://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:UFPB2021-06-22T23:03:27Zoai:repositorio.ufpb.br:123456789/19954Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2021-06-22T23:03:27Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
title |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
spellingShingle |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana Silva, Everton da Paz Tiossemicarbazonas β-tiofenilsemicarbazonas Atividade antibacteriana Derivados de isatina Síntese em micro-ondas Thiosemicarbazones β-phenylthiosemicarbazones Antibacterial activity Isatin derivatives Microwave synthesis CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
title_full |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
title_fullStr |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
title_full_unstemmed |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
title_sort |
Síntese de β-feniltiossemicarbazonas derivadas de isatina e estudo in vitro da atividade antibacteriana |
author |
Silva, Everton da Paz |
author_facet |
Silva, Everton da Paz |
author_role |
author |
dc.contributor.none.fl_str_mv |
Lima Junior, Claudio Gabriel http://lattes.cnpq.br/5743384737397873 |
dc.contributor.author.fl_str_mv |
Silva, Everton da Paz |
dc.subject.por.fl_str_mv |
Tiossemicarbazonas β-tiofenilsemicarbazonas Atividade antibacteriana Derivados de isatina Síntese em micro-ondas Thiosemicarbazones β-phenylthiosemicarbazones Antibacterial activity Isatin derivatives Microwave synthesis CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Tiossemicarbazonas β-tiofenilsemicarbazonas Atividade antibacteriana Derivados de isatina Síntese em micro-ondas Thiosemicarbazones β-phenylthiosemicarbazones Antibacterial activity Isatin derivatives Microwave synthesis CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The indole nucleus, contained in isatin, is present in several bioactive molecules and this makes isatin an excellent synthetic block for the development of new potentially active compounds. Isatin derivatives are commonly reported in the literature with different biological activities and thiosemicarbazones stand out for their synthetic simplicity and high biological potential. Thus, this work aimed of analogous series synthesis of β-phenyl thiosemicarbazones derived from isatin by irradiation of microwave and investigation of antibacterial activity. Among these compounds, eight are unpublished. Preliminary experiments were carried out by varying the parameters of catalysis, temperature and reaction time in order to define a general method of synthesis to obtain the compounds. Isatin derivatives were prepared and used as intermediates in the synthesis of thiosemicarbazones. The series of β-thiophenylsemicarbazones was obtained in reactions assisted by microwave radiation, lasting 10 min in the presence of acetic acid as a catalyst. The yields obtained varied from 50-94% and were compared with those presented in the literature. All compounds were characterized by 13C and 1H NMR spectroscopy. The method developed for the synthesis of these compounds in microwave reactor proved to be a useful and efficient to obtain the products in a short reaction time. The in silico study was carried out and indicated that the compounds are in compliance with the rule of Lipinski and ADME, presenting a satisfactory oral bioavailability. The compounds were evaluated for antibacterial activity in the strains of S. aureus, E. coli and P. aeruginosa and thiosemicarbazone derived from 5-chloro-1-methyl-isatin (64) was the only one capable of inhibiting the growth of microorganisms with MIC of 562.5 μg / mL, indicating strong inhibitory activity. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-03-12 2020-03-09 2021-04-15T19:40:53Z 2021-04-15T19:40:53Z |
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/123456789/19954 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/19954 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
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 |
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1797057869021970432 |