Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol

Detalhes bibliográficos
Ano de defesa: 2015
Autor(a) principal: Santos, Alexsandro Fernandes dos lattes
Orientador(a): Athayde Filho, Antonio Filgueiras de lattes
Banca de defesa: Não Informado pela instituição
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal da Paraíba
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
1,3,4-oxadiazol
Atividade Bactericida
Atividade Fungicida
Estudo cristalográfico
Espectroscopia de Massa
Palavras-chave em Inglês:
1,3,4-oxadiazole
Bactericide activity
Fungicide activity
Crystallographic study
Mass spectroscopy
Área do conhecimento CNPq:
CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: https://repositorio.ufpb.br/jspui/handle/tede/9010
Resumo: Two series based on the structure of 2,5-diaryl-1,3,4-oxadiazole were synthesized, 2-aryl-5-methyl-1,3,4-oxadiazole (1a,h) and 2-aryl-5- trifluoromethyl-1,3,4-oxadiazole (2a,e), and their biological activity were investigated. These compounds had their chemical structures characterized with spectrometric methods such as IR, 1H and 13C NMR. To characterize the compound 2-(2-acetoxyphenyl)-5-methyl-1,3,4- oxadiazole, it was necessary the use of two-dimensional NMR techniques (COSY, HMQC and HMBC) and his structural arrangement was analyzed by the crystallographic X-ray technique. Mass spectrometric investigation, unprecedented for this class of compound, was also performed. All compounds were tested against eight strains of Staphylococcus aureus, Escherichia coli and also against strains of Aspegilles fumigatus, Aspegilles flavus, Candida albicans, Candida albicans and Candida tropicalis. The results showed that compounds 1b, 1c, 1e, 1g, 2a and 2c, produced inhibition on the growth of species of bacteria and fungi, where the MIC was set between 512 to 1224 mg mL-1. While the compounds 1d, 1e, 1f, 1h, 2a and 2b were inactive, the compounds 1d, 1e, 1f, 1h, 2a and 2b reported a broad spectrum.
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spelling 2017-06-21T12:11:14Z2018-07-21T00:30:10Z2018-07-21T00:30:10Z2015-07-29SANTOS, Alexsandro Fernandes dos. Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol. 2015. 190 f. Tese (Doutorado em Química) - Universidade Federal da Paraíba, João Pessoa, 2015.https://repositorio.ufpb.br/jspui/handle/tede/9010Two series based on the structure of 2,5-diaryl-1,3,4-oxadiazole were synthesized, 2-aryl-5-methyl-1,3,4-oxadiazole (1a,h) and 2-aryl-5- trifluoromethyl-1,3,4-oxadiazole (2a,e), and their biological activity were investigated. These compounds had their chemical structures characterized with spectrometric methods such as IR, 1H and 13C NMR. To characterize the compound 2-(2-acetoxyphenyl)-5-methyl-1,3,4- oxadiazole, it was necessary the use of two-dimensional NMR techniques (COSY, HMQC and HMBC) and his structural arrangement was analyzed by the crystallographic X-ray technique. Mass spectrometric investigation, unprecedented for this class of compound, was also performed. All compounds were tested against eight strains of Staphylococcus aureus, Escherichia coli and also against strains of Aspegilles fumigatus, Aspegilles flavus, Candida albicans, Candida albicans and Candida tropicalis. The results showed that compounds 1b, 1c, 1e, 1g, 2a and 2c, produced inhibition on the growth of species of bacteria and fungi, where the MIC was set between 512 to 1224 mg mL-1. While the compounds 1d, 1e, 1f, 1h, 2a and 2b were inactive, the compounds 1d, 1e, 1f, 1h, 2a and 2b reported a broad spectrum.Duas séries do heterocíclico 1,3,4-oxadiazol foram sintetizadas, a 2-aril-5-metil-1,3,4-oxadiazol (1a, h) e a 2-aril-5-trifluormetil-1,3,4- oxadiazol (2a, e), obtendo cinco moléculas inéditas (1a, 1e, 2a, 2c e 2e). Todas as moléculas obtidas foram caracterizados pelas técnicas espectroscópicas de 1D de RMN 1H e 13C, IV e realizado o estudo inédito de espectroscopia de Massas. Para a caracterização do composto 2-(2- acetoxifenil)-5-metil-1,3,4-oxadiazol se fez necessário a utilização das técnicas bidimensionais de RMN COSY, HMQC e HMBC, bem como seu arranjo estrutural foi analisado pela técnica cristalográfica de Raios-X. Os oxadiazóis obtidos foram avaliadas frente a oito cepas de Staphylococcus aureus e Escherichia coli e oito cepas, incluindo, Aspegilles fumigatus ATCC 16913, Aspegilles flavus, Candida albicans, Candida albicans e Candida tropicalis. Os ensaios para avaliações da atividade biológica dos produtos foram realizados pela técnica de microdiluição em meio líquido, onde foi determinada a concentração Inibitória Mínima (CIM). Os resultados mostraram que os compostos (1b), (1c), (1e), (1g), (2a) e (2c), produziram inibição sobre o crescimento de espécies de bactérias e de fungos, onde a CIM ficou estabelecida entre 512 a 1224 mg/ml. Enquanto que os compostos 1d, 1e, 1f, 1h, 2a e 2b se apresentaram inativos. Já os compostos 1d, 1e, 1f, 1h, 2a e 2b relataram um amplo espectro.Submitted by Maike Costa (maiksebas@gmail.com) on 2017-06-21T12:11:13Z No. of bitstreams: 1 arquivototal.pdf: 5280829 bytes, checksum: 081debefa3f10398a1c9461855ba5b9d (MD5)Made available in DSpace on 2017-06-21T12:11:14Z (GMT). No. of bitstreams: 1 arquivototal.pdf: 5280829 bytes, checksum: 081debefa3f10398a1c9461855ba5b9d (MD5) Previous issue date: 2015-07-29Made available in DSpace on 2018-07-21T00:30:10Z (GMT). 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dc.title.por.fl_str_mv Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
title Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
spellingShingle Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
Santos, Alexsandro Fernandes dos
1,3,4-oxadiazol
Atividade Bactericida
Atividade Fungicida
Estudo cristalográfico
Espectroscopia de Massa
1,3,4-oxadiazole
Bactericide activity
Fungicide activity
Crystallographic study
Mass spectroscopy
CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
title_full Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
title_fullStr Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
title_full_unstemmed Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
title_sort Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol
author Santos, Alexsandro Fernandes dos
author_facet Santos, Alexsandro Fernandes dos
author_role author
dc.contributor.advisor1.fl_str_mv Athayde Filho, Antonio Filgueiras de
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/1717412318563908
dc.contributor.authorID.fl_str_mv 05570370420
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/7188428497340854
dc.contributor.author.fl_str_mv Santos, Alexsandro Fernandes dos
contributor_str_mv Athayde Filho, Antonio Filgueiras de
dc.subject.por.fl_str_mv 1,3,4-oxadiazol
Atividade Bactericida
Atividade Fungicida
Estudo cristalográfico
Espectroscopia de Massa
topic 1,3,4-oxadiazol
Atividade Bactericida
Atividade Fungicida
Estudo cristalográfico
Espectroscopia de Massa
1,3,4-oxadiazole
Bactericide activity
Fungicide activity
Crystallographic study
Mass spectroscopy
CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv 1,3,4-oxadiazole
Bactericide activity
Fungicide activity
Crystallographic study
Mass spectroscopy
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA
description Two series based on the structure of 2,5-diaryl-1,3,4-oxadiazole were synthesized, 2-aryl-5-methyl-1,3,4-oxadiazole (1a,h) and 2-aryl-5- trifluoromethyl-1,3,4-oxadiazole (2a,e), and their biological activity were investigated. These compounds had their chemical structures characterized with spectrometric methods such as IR, 1H and 13C NMR. To characterize the compound 2-(2-acetoxyphenyl)-5-methyl-1,3,4- oxadiazole, it was necessary the use of two-dimensional NMR techniques (COSY, HMQC and HMBC) and his structural arrangement was analyzed by the crystallographic X-ray technique. Mass spectrometric investigation, unprecedented for this class of compound, was also performed. All compounds were tested against eight strains of Staphylococcus aureus, Escherichia coli and also against strains of Aspegilles fumigatus, Aspegilles flavus, Candida albicans, Candida albicans and Candida tropicalis. The results showed that compounds 1b, 1c, 1e, 1g, 2a and 2c, produced inhibition on the growth of species of bacteria and fungi, where the MIC was set between 512 to 1224 mg mL-1. While the compounds 1d, 1e, 1f, 1h, 2a and 2b were inactive, the compounds 1d, 1e, 1f, 1h, 2a and 2b reported a broad spectrum.
publishDate 2015
dc.date.issued.fl_str_mv 2015-07-29
dc.date.accessioned.fl_str_mv 2017-06-21T12:11:14Z
2018-07-21T00:30:10Z
dc.date.available.fl_str_mv 2018-07-21T00:30:10Z
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dc.identifier.citation.fl_str_mv SANTOS, Alexsandro Fernandes dos. Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol. 2015. 190 f. Tese (Doutorado em Química) - Universidade Federal da Paraíba, João Pessoa, 2015.
dc.identifier.uri.fl_str_mv https://repositorio.ufpb.br/jspui/handle/tede/9010
identifier_str_mv SANTOS, Alexsandro Fernandes dos. Síntese, Caracterização e Avaliação Antimicrobiana de Novos Derivados do Sistema 1,3,4-oxadiazol. 2015. 190 f. Tese (Doutorado em Química) - Universidade Federal da Paraíba, João Pessoa, 2015.
url https://repositorio.ufpb.br/jspui/handle/tede/9010
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dc.publisher.initials.fl_str_mv UFPB
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal da Paraíba
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