Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Acta Brasiliensis (Online) |
Texto Completo: | http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/555 |
Resumo: | Compounds containing heterocyclic ring systems are of great importance both medicinally and industrially. Five-membered 1,2,4-oxadiazole heterocycles have received considerable attention because of their unique bioisosteric properties and unusual wide spectrum of biological activities. In this study, a series of 2-(3-aryl-1,2,4-oxadiazol-5-yl)-trans-3,4-(methylenedioxy)-cinnamyl derivatives was synthesized and characterized, and in vitro experimental models were used to evaluate their antimicrobial activity. Synthesis, which involved microwave irradiation for 5 min, provided moderate yields of 1,2,4-oxadiazole (34–50%). Infrared (IR) and nuclear magnetic resonance (1H NMR and 13C NMR) spectroscopy were used to determine the structures of 1,2,4-oxadiazole. The disk diffusion method was used to test the antibacterial activity of the novel 1,2,4-oxadiazole derivatives against Gram-positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) and Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria. The derivatives, 2-(3-m-toluyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl and 2-(3-pyrimidyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl exhibited a minimum inhibitory concentration (MIC) of 19.5 μg mL−1 against S. aureus, and is four-fold more potent than the standard metronidazole (MIC =78 μg mL−1). |
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Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid Síntese, caracterização e avaliação antimicrobiana de 1,2,4-oxadiazóis derivados do ácido trans-3,4-(metilenodioxi)-cinâmicoCompounds containing heterocyclic ring systems are of great importance both medicinally and industrially. Five-membered 1,2,4-oxadiazole heterocycles have received considerable attention because of their unique bioisosteric properties and unusual wide spectrum of biological activities. In this study, a series of 2-(3-aryl-1,2,4-oxadiazol-5-yl)-trans-3,4-(methylenedioxy)-cinnamyl derivatives was synthesized and characterized, and in vitro experimental models were used to evaluate their antimicrobial activity. Synthesis, which involved microwave irradiation for 5 min, provided moderate yields of 1,2,4-oxadiazole (34–50%). Infrared (IR) and nuclear magnetic resonance (1H NMR and 13C NMR) spectroscopy were used to determine the structures of 1,2,4-oxadiazole. The disk diffusion method was used to test the antibacterial activity of the novel 1,2,4-oxadiazole derivatives against Gram-positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) and Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria. The derivatives, 2-(3-m-toluyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl and 2-(3-pyrimidyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl exhibited a minimum inhibitory concentration (MIC) of 19.5 μg mL−1 against S. aureus, and is four-fold more potent than the standard metronidazole (MIC =78 μg mL−1).Os compostos que contêm sistemas de anéis heterocíclicos são de grande importância tanto na medicina quanto na indústria. O anel heterocíclico de 1,2,4-oxadiazol de cinco membros tem recebido atenção considerável por causa de suas propriedades bioisostéricas únicas e um espectro excepcionalmente amplo de atividades biológicas. Este estudo teve como objetivo a síntese, a caracterização e a avaliação da atividade antimicrobiana de uma série de 2-(3-aril-1,2,4-oxadiazol-5-il)-trans-3,4-(metilenodioxi)-cinamila usando modelos experimentais in vitro. A síntese dos 1,2,4-oxadiazóis foi desenvolvida, com duração de 5 min, usando irradiação de micro-ondas fornecendo os compostos em rendimentos moderados (34-50%). Suas estruturas foram determinadas usando espectroscopia de IV (Infravermelho), Resonância magnética nuclear de hidrogênio (RMN 1H) () eRessonancia magnética nuclear de carbono 13 (RMN 13C). As atividades antibacterianas dos novos derivados de 1,3,4-oxadiazóis foram testado contra Gram positivo (Bacillus subtilis, Enterococcus faecalis e Staphylococcus aureus) e Gram negativo (Escherichia coli e Klebsiella pneumoniae) bactérias usando o método de difusão em disco. Os 2-(3-m-toluil-1,2,4-oxadiazol-5-il)-3,4-(metilenodioxi)-cinamila e o 2-(3-pirimidil-1,2,4-oxadiazol-5-il)-3,4-(metilenodioxi)- cinamila apresentaram resultados contra S. aureus, com valor de CIM de 19,5 μg mL-1 quatro vezes mais potente que o metronidazol padrão (CIM=78 μg mL-1). Universidade Federal de Campina Grande - UFCG2022-01-31info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/55510.22571/2526-4338555Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-13Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-13Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-132526-43382526-432Xreponame:Acta Brasiliensis (Online)instname:Universidade Federal de Campina Grande (UFCG)instacron:UFCGenghttp://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/555/138Copyright (c) 2022 Acta Brasiliensisinfo:eu-repo/semantics/openAccessde Freitas Filho, João RufinoRamos, Clécio SouzaBarros Bezerra, Leonardo AlexandreFonte Silva, Marcílio WagnerBezerra, Giselle Barbosade Freitas, Jucleiton José RufinoBarbosa Freitas, Queila Patrícia da Silva2022-01-31T23:17:40Zoai:ActaBra.revistas.ufcg.edu.br:article/555Revistahttp://revistas.ufcg.edu.br/ActaBraPUBhttp://revistas.ufcg.edu.br/ActaBra/index.php/actabra/oaiactabrasiliensis@gmail.com || actabrasiliensis@gmail.com2526-432X2526-4338opendoar:2022-01-31T23:17:40Acta Brasiliensis (Online) - Universidade Federal de Campina Grande (UFCG)false |
dc.title.none.fl_str_mv |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid Síntese, caracterização e avaliação antimicrobiana de 1,2,4-oxadiazóis derivados do ácido trans-3,4-(metilenodioxi)-cinâmico |
title |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
spellingShingle |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid de Freitas Filho, João Rufino |
title_short |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
title_full |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
title_fullStr |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
title_full_unstemmed |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
title_sort |
Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid |
author |
de Freitas Filho, João Rufino |
author_facet |
de Freitas Filho, João Rufino Ramos, Clécio Souza Barros Bezerra, Leonardo Alexandre Fonte Silva, Marcílio Wagner Bezerra, Giselle Barbosa de Freitas, Jucleiton José Rufino Barbosa Freitas, Queila Patrícia da Silva |
author_role |
author |
author2 |
Ramos, Clécio Souza Barros Bezerra, Leonardo Alexandre Fonte Silva, Marcílio Wagner Bezerra, Giselle Barbosa de Freitas, Jucleiton José Rufino Barbosa Freitas, Queila Patrícia da Silva |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
de Freitas Filho, João Rufino Ramos, Clécio Souza Barros Bezerra, Leonardo Alexandre Fonte Silva, Marcílio Wagner Bezerra, Giselle Barbosa de Freitas, Jucleiton José Rufino Barbosa Freitas, Queila Patrícia da Silva |
description |
Compounds containing heterocyclic ring systems are of great importance both medicinally and industrially. Five-membered 1,2,4-oxadiazole heterocycles have received considerable attention because of their unique bioisosteric properties and unusual wide spectrum of biological activities. In this study, a series of 2-(3-aryl-1,2,4-oxadiazol-5-yl)-trans-3,4-(methylenedioxy)-cinnamyl derivatives was synthesized and characterized, and in vitro experimental models were used to evaluate their antimicrobial activity. Synthesis, which involved microwave irradiation for 5 min, provided moderate yields of 1,2,4-oxadiazole (34–50%). Infrared (IR) and nuclear magnetic resonance (1H NMR and 13C NMR) spectroscopy were used to determine the structures of 1,2,4-oxadiazole. The disk diffusion method was used to test the antibacterial activity of the novel 1,2,4-oxadiazole derivatives against Gram-positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) and Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria. The derivatives, 2-(3-m-toluyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl and 2-(3-pyrimidyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl exhibited a minimum inhibitory concentration (MIC) of 19.5 μg mL−1 against S. aureus, and is four-fold more potent than the standard metronidazole (MIC =78 μg mL−1). |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-01-31 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/555 10.22571/2526-4338555 |
url |
http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/555 |
identifier_str_mv |
10.22571/2526-4338555 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
http://revistas.ufcg.edu.br/ActaBra/index.php/actabra/article/view/555/138 |
dc.rights.driver.fl_str_mv |
Copyright (c) 2022 Acta Brasiliensis info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Copyright (c) 2022 Acta Brasiliensis |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Campina Grande - UFCG |
publisher.none.fl_str_mv |
Universidade Federal de Campina Grande - UFCG |
dc.source.none.fl_str_mv |
Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-13 Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-13 Acta Brasiliensis; Vol 6 No 1 (2022): Acta Brasiliensis; 6-13 2526-4338 2526-432X reponame:Acta Brasiliensis (Online) instname:Universidade Federal de Campina Grande (UFCG) instacron:UFCG |
instname_str |
Universidade Federal de Campina Grande (UFCG) |
instacron_str |
UFCG |
institution |
UFCG |
reponame_str |
Acta Brasiliensis (Online) |
collection |
Acta Brasiliensis (Online) |
repository.name.fl_str_mv |
Acta Brasiliensis (Online) - Universidade Federal de Campina Grande (UFCG) |
repository.mail.fl_str_mv |
actabrasiliensis@gmail.com || actabrasiliensis@gmail.com |
_version_ |
1792204524140625920 |