Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFPB |
Texto Completo: | https://repositorio.ufpb.br/jspui/handle/123456789/19744 |
Resumo: | This work describes the synthesis, characterization and antifungal potential and antibiofilm of eighteen monoterpene derivatives, nine of which are derived from eugenol and nine from isoeugenol. The synthesis of these compounds, which yielded satisfactory yields (74 to 92%), occurred in two steps: nine acetamides were initially synthesized and then these were derivatized with eugenol and isoeugenol separately in an etherification reaction of type SN2. All compounds, acetamides and derivatives were characterized by IR spectroscopic techniques, 1 H and 13 C NMR and the antifungal potential of the derivatives against Candida albicans strains and antibiofilm activity against Escherichia coli and Staphilococcus aureus were evaluated. Among the eighteen derivatives investigated, antifungal studies indicated that isoeugenol (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N-phenylacetamide and (E) - N- (4chlorophenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and the eugenol derivative 2- (4-allyl-2-methoxyphenoxy) -N- (4-allyl-2-methoxyphenyl) -N- (4-chloro-3-nitrophenyl) acetamide showed a strong inhibitory activity of 85 % of strains of the genus Candida. Anti-adherent activity was observed in six of the ten isoeugenol derivatives against E. coli, and the adhesion of only 2.9% of the isoeugenol (E) -2- (2-methoxy-4- (prop-1- en-1-yl) phenoxy) -N-phenylacetamide. For S. aureus, derivatives of isoeugenol (E) -N- (4-ethylphenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and (E) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (p-tolyl) acetamide exhibited excellent non-stick activity of less than 10%, and eugenol derivatives showed non-stick activity between 3.72 and 90.43%. All eugenol derivatives showed less than 10% antibiofilm activity against E. coli. Antibacterial studies showed that the lowest MIC was observed in the compound (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (4-methoxyphenyl) acetamide E. coli (35 μg / mL) and 2- (4-allyl-2-methoxyphenoxy) -N- (4-chloro-3-nitrophenyl) acetamide (66.8 μg / mL) for S. aureus. Quantitative Structure-Activity Relationships (QSAR) studies indicated that the descriptors that contributed significantly and positively to the isoeugenol series are DIFF (diffusivity, control of chemical dispersion in water at 25 ° C) and CP (critical packaging parameter) , whereas for the eugenol series only the descriptor V (molecular volume) which influences increasing, that is, a larger volume in an aqueous solution and greater repulsion to water results in considerable antifungal activity. |
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Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilmeDerivados do eugenolDerivados do isoeugenolAcetamidas substituídasCandida albicansStaphilococcus aureusEugenol derivativesIsoeugenol derivativesSubstituted acetamidesCNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIAThis work describes the synthesis, characterization and antifungal potential and antibiofilm of eighteen monoterpene derivatives, nine of which are derived from eugenol and nine from isoeugenol. The synthesis of these compounds, which yielded satisfactory yields (74 to 92%), occurred in two steps: nine acetamides were initially synthesized and then these were derivatized with eugenol and isoeugenol separately in an etherification reaction of type SN2. All compounds, acetamides and derivatives were characterized by IR spectroscopic techniques, 1 H and 13 C NMR and the antifungal potential of the derivatives against Candida albicans strains and antibiofilm activity against Escherichia coli and Staphilococcus aureus were evaluated. Among the eighteen derivatives investigated, antifungal studies indicated that isoeugenol (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N-phenylacetamide and (E) - N- (4chlorophenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and the eugenol derivative 2- (4-allyl-2-methoxyphenoxy) -N- (4-allyl-2-methoxyphenyl) -N- (4-chloro-3-nitrophenyl) acetamide showed a strong inhibitory activity of 85 % of strains of the genus Candida. Anti-adherent activity was observed in six of the ten isoeugenol derivatives against E. coli, and the adhesion of only 2.9% of the isoeugenol (E) -2- (2-methoxy-4- (prop-1- en-1-yl) phenoxy) -N-phenylacetamide. For S. aureus, derivatives of isoeugenol (E) -N- (4-ethylphenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and (E) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (p-tolyl) acetamide exhibited excellent non-stick activity of less than 10%, and eugenol derivatives showed non-stick activity between 3.72 and 90.43%. All eugenol derivatives showed less than 10% antibiofilm activity against E. coli. Antibacterial studies showed that the lowest MIC was observed in the compound (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (4-methoxyphenyl) acetamide E. coli (35 μg / mL) and 2- (4-allyl-2-methoxyphenoxy) -N- (4-chloro-3-nitrophenyl) acetamide (66.8 μg / mL) for S. aureus. Quantitative Structure-Activity Relationships (QSAR) studies indicated that the descriptors that contributed significantly and positively to the isoeugenol series are DIFF (diffusivity, control of chemical dispersion in water at 25 ° C) and CP (critical packaging parameter) , whereas for the eugenol series only the descriptor V (molecular volume) which influences increasing, that is, a larger volume in an aqueous solution and greater repulsion to water results in considerable antifungal activity.NenhumaNeste trabalho descreve-se a síntese, caracterização e potencial antifúngico e antibiofilme de dezoito derivados de monoterpenos, sendo nove derivados do eugenol e outros nove do isoeugenol. A síntese desses compostos, que apresentou rendimentos satisfatórios (74 a 92 %), ocorreu em duas etapas: inicialmente foram sintetizadas nove acetamidas e em seguida estas foram derivatizadas com o eugenol e o isoeugenol, separadamente, em uma reação de eterificação do tipo SN2. Todos os compostos, acetamidas e derivados, foram caracterizados por técnicas espectroscópicas de IV, RMN de 1H e 13C e avaliou-se o potencial antifúngico dos derivados contra cepas de Candida albicans e a atividade antibiofilme contra Escherichia coli e Staphilococcus aureus. Dentre os dezoito derivados investigados, os estudos antifúngicos indicaram que os derivados do isoeugenol (E)-2-(2-metóxi-4(prop-1-en-1-il)fenóxi)-N-fenilacetamida e (E)-N-(4-clorofenil)-2-(2-metóxi-4-(prop1-en-1-il)fenóxi)acetamida e o derivado do eugenol 2-(4-alil-2-metóxifenóxi)-N-(4metóxifenil)acetamida inibiram moderadamente o crescimento das espécies de Candida e o derivado do eugenol 2-(4-alil-2-metóxifenóxi)-N-(4-cloro-3nitrofenil)acetamida apresentou uma forte atividade inibitória de 85 % das cepas do gênero Candida. A atividade antiaderente foi observada em seis dos dez derivados do isoeugenol frente a E. coli, sendo evidenciado a aderência de apenas 2,9% do derivado do isoeugenol (E)-2-(2-metóxi-4-(prop-1-en-1-il)fenóxi)-N-fenilacetamida. Em relação a S. aureus, os derivados do isoeugenol (E)-N-(4-etilfenil)-2-(2-metóxi-4(prop-1-en-1-il)fenóxi)acetamida e (E)-2-(2-metóxi-4-(prop-1-en-1-il)fenóxi)-N-(ptolil)acetamida apresentaram atividade antiaderente inferior a 10%, e os derivados do eugenol apresentaram atividade antiaderente entre 3,72 e 90,43%. Todos os derivados do eugenol apresentaram atividade antibiofilme inferior a 10% contra E. coli. Os estudos antibacterianos mostraram que a mais baixa CIM foi observada no composto (E)-2-(2-metóxi-4-(prop-1-en-1-il)fenóxi)-N-(4-metóxifenil)acetamida frente a E. coli (35 μg/mL) e por 2-(4-alil-2-metóxifenóxi)-N-(4-cloro-3-nitrofenil)acetamida (66,8 μg/mL) para S. aureus. Os estudos de relações quantitativas estrutura-atividade (QSAR) indicaram que os descritores que contribuíram significativa e positivamente para a série do isoeugenol são os DIFF (difusividade, controle da dispersão química em água a 25°C) e CP (Parâmetro de embalagem crítica), enquanto, para a série do eugenol, apenas o descritor V (volume molecular) o qual influencia de forma crescente, ou seja, um maior volume em uma solução aquosa e maior repulsão à agua resulta em atividade antifúngica considerável.Universidade Federal da ParaíbaBrasilFarmacologiaPrograma de Pós-Graduação em Produtos Naturais e Sintéticos BioativosUFPBBarbosa Filho, José Mariahttp://lattes.cnpq.br/8892459126928726Athayde Filho, Petrônio FilgueirasJardim, Jeane Uilma Galindo2021-03-17T14:51:55Z2019-09-302021-03-17T14:51:55Z2019-08-30info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesishttps://repositorio.ufpb.br/jspui/handle/123456789/19744porhttp://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:UFPB2021-06-29T13:30:50Zoai:repositorio.ufpb.br:123456789/19744Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2021-06-29T13:30:50Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
title |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
spellingShingle |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme Jardim, Jeane Uilma Galindo Derivados do eugenol Derivados do isoeugenol Acetamidas substituídas Candida albicans Staphilococcus aureus Eugenol derivatives Isoeugenol derivatives Substituted acetamides CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
title_short |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
title_full |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
title_fullStr |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
title_full_unstemmed |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
title_sort |
Derivados do eugenol e isoeugenol e suas potencialidades antifúngica e antibiofilme |
author |
Jardim, Jeane Uilma Galindo |
author_facet |
Jardim, Jeane Uilma Galindo |
author_role |
author |
dc.contributor.none.fl_str_mv |
Barbosa Filho, José Maria http://lattes.cnpq.br/8892459126928726 Athayde Filho, Petrônio Filgueiras |
dc.contributor.author.fl_str_mv |
Jardim, Jeane Uilma Galindo |
dc.subject.por.fl_str_mv |
Derivados do eugenol Derivados do isoeugenol Acetamidas substituídas Candida albicans Staphilococcus aureus Eugenol derivatives Isoeugenol derivatives Substituted acetamides CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
topic |
Derivados do eugenol Derivados do isoeugenol Acetamidas substituídas Candida albicans Staphilococcus aureus Eugenol derivatives Isoeugenol derivatives Substituted acetamides CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
description |
This work describes the synthesis, characterization and antifungal potential and antibiofilm of eighteen monoterpene derivatives, nine of which are derived from eugenol and nine from isoeugenol. The synthesis of these compounds, which yielded satisfactory yields (74 to 92%), occurred in two steps: nine acetamides were initially synthesized and then these were derivatized with eugenol and isoeugenol separately in an etherification reaction of type SN2. All compounds, acetamides and derivatives were characterized by IR spectroscopic techniques, 1 H and 13 C NMR and the antifungal potential of the derivatives against Candida albicans strains and antibiofilm activity against Escherichia coli and Staphilococcus aureus were evaluated. Among the eighteen derivatives investigated, antifungal studies indicated that isoeugenol (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N-phenylacetamide and (E) - N- (4chlorophenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and the eugenol derivative 2- (4-allyl-2-methoxyphenoxy) -N- (4-allyl-2-methoxyphenyl) -N- (4-chloro-3-nitrophenyl) acetamide showed a strong inhibitory activity of 85 % of strains of the genus Candida. Anti-adherent activity was observed in six of the ten isoeugenol derivatives against E. coli, and the adhesion of only 2.9% of the isoeugenol (E) -2- (2-methoxy-4- (prop-1- en-1-yl) phenoxy) -N-phenylacetamide. For S. aureus, derivatives of isoeugenol (E) -N- (4-ethylphenyl) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) acetamide and (E) -2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (p-tolyl) acetamide exhibited excellent non-stick activity of less than 10%, and eugenol derivatives showed non-stick activity between 3.72 and 90.43%. All eugenol derivatives showed less than 10% antibiofilm activity against E. coli. Antibacterial studies showed that the lowest MIC was observed in the compound (E) 2- (2-methoxy-4- (prop-1-en-1-yl) phenoxy) -N- (4-methoxyphenyl) acetamide E. coli (35 μg / mL) and 2- (4-allyl-2-methoxyphenoxy) -N- (4-chloro-3-nitrophenyl) acetamide (66.8 μg / mL) for S. aureus. Quantitative Structure-Activity Relationships (QSAR) studies indicated that the descriptors that contributed significantly and positively to the isoeugenol series are DIFF (diffusivity, control of chemical dispersion in water at 25 ° C) and CP (critical packaging parameter) , whereas for the eugenol series only the descriptor V (molecular volume) which influences increasing, that is, a larger volume in an aqueous solution and greater repulsion to water results in considerable antifungal activity. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-09-30 2019-08-30 2021-03-17T14:51:55Z 2021-03-17T14:51:55Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufpb.br/jspui/handle/123456789/19744 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/19744 |
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 Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos UFPB |
publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos 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) |
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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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1801842971331526656 |