Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos

Detalhes bibliográficos
Autor(a) principal: Pinheiro, Patrícia Fontes
Data de Publicação: 2009
Tipo de documento: Tese
Idioma: por
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: http://locus.ufv.br/handle/123456789/207
Resumo: Nostoclides are natural substances isolated from blue-green seaweed, Nostoc sp., found in a lichen called Peltigera canina. They belong to the class of compounds known as γ-alkylidenebutenolides. Nostoclides have been used as model compounds aimed the discovery of new herbicides. Compounds 3-benzyl-5-arylidenefuran-2-(5H)-ones, analogues to nostoclides devoid of the isopropyl group were synthesized and phytotoxicity of these compounds was evaluated in vitro for their ability to interfere in electron transport directed by light, water to the non-biological oxidant potassium ferricyanide. For this experiment were used chloroplasts isolated from spinach (Spinacia oleracea). In this study, we look for an understanding of the different parameters involved in the correlation between chemical structure of different analogues nostoclides to those described in the literature and biological activity (ability of analogues to interfere with electron transport in chloroplasts isolated from spinach) of these compounds. For this purpose, we used the software CODESSA (COmprehensive DEscriptors for Structural and Statistical Analysis). We developed two mathematical models, in both models, the descriptor of greater significance was selected 'Image of the Onasager-Kirkwood solvation energy' (SEOK), which relates indirectly to phytotoxicity with the polarity of the molecules. In the present investigation, compounds analogues to nostoclides containing the isopropyl group in position 4 of the lactone ring were synthesized in order to assess the impact of this in the biological activity. For the synthesis of these compounds, compound 3,4-dibromofuran-2(5H)-one was used as starting material. This compound in the presence of isopropyl magnesium bromide, copper iodide and chloride trimethylsilane, led to the synthesis of compound 3-bromo-4-isopropylfuran-2(5H)-one, with 48% yield. The reaction conditions for the synthesis of this compound were optimized. Yields were calculated by the Internal Standard Method using gas chromatography. The compound 3-benzyl-4-isopropylfuran-2(5H)-one, reagent used in the synthesis of analogues to nostoclides, was synthesized from the lactone 3-bromo-4-isopropylfuran-2 (5H)-one by Negishi coupling, using Pd(PPh)4 in DMF:THF/1:1, this compound was obtained with 36% yield. Subsequently, the substance 3-benzyl-4-isopropylfuran-2 (5H)-one was subjected to alkylidenation reactions with differently substituted aromatic aldehydes. Reactions were performed in the presence of diisopropylethylamine (DIPEA) and trifluoromethanesulfonate of tert-butyldimethylsilile (TBDMSOTf), at room temperature. The aldol intermediate obtained were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under reflux conditions, which resulted in 5 analogues nostoclides substances, with yields ranging from 22-86%. New γ-alkylidenebutenolides belonging to the class of 3,4-dihalo-5-arylidenefuran-2(5H)-ones were prepared from the lactones 3,4-dihalofuran-2(5H)-ones and different aromatic aldehydes by alkylidenation reaction already mentioned. Compounds analogues to nostoclides as 3,4-dihalo-5-arylidenefuran-2(5H)-ones and several lactones precursors were evaluated in vitro for their ability to inhibit the growth of three species of bacteria, E. coli, S. aureus and B. cereus, testing by disk-diffusion. Analogues to nostoclides tested showed no inhibition to none of the bacteria tested. The compounds belonging to the class of 3,4-dihalo-5-arylidenefuran-2 (5H)-ones and lactones 3,4-dibromofuran-2(5H)-one and 3,4-dichlorofuran-2(5H)-one showed inhibition against the different bacteria and they are considered potential antimicrobial agents.
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spelling Pinheiro, Patrícia Fonteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4223016U2Maltha, Célia Regina álvareshttp://lattes.cnpq.br/7346715444030145Demuner, Antônio Jacintohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783217D3Barbosa, Luiz Claudio de Almeidahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2Fernandes, Sergio Antôniohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4760152Y5Gil, Laurent Frederichttp://lattes.cnpq.br/6301871767422750Conceição, Gelson José Andrade dahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723800Z82015-03-26T12:05:56Z2011-06-062015-03-26T12:05:56Z2009-10-19PINHEIRO, Patrícia Fontes. Study of the quantitative relationship chemical structurebiological activity of analogous compounds to nostoclides and synthesis of new γ-alkylidenebutenolides. 2009. 186 f. Tese (Doutorado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2009.http://locus.ufv.br/handle/123456789/207Nostoclides are natural substances isolated from blue-green seaweed, Nostoc sp., found in a lichen called Peltigera canina. They belong to the class of compounds known as γ-alkylidenebutenolides. Nostoclides have been used as model compounds aimed the discovery of new herbicides. Compounds 3-benzyl-5-arylidenefuran-2-(5H)-ones, analogues to nostoclides devoid of the isopropyl group were synthesized and phytotoxicity of these compounds was evaluated in vitro for their ability to interfere in electron transport directed by light, water to the non-biological oxidant potassium ferricyanide. For this experiment were used chloroplasts isolated from spinach (Spinacia oleracea). In this study, we look for an understanding of the different parameters involved in the correlation between chemical structure of different analogues nostoclides to those described in the literature and biological activity (ability of analogues to interfere with electron transport in chloroplasts isolated from spinach) of these compounds. For this purpose, we used the software CODESSA (COmprehensive DEscriptors for Structural and Statistical Analysis). We developed two mathematical models, in both models, the descriptor of greater significance was selected 'Image of the Onasager-Kirkwood solvation energy' (SEOK), which relates indirectly to phytotoxicity with the polarity of the molecules. In the present investigation, compounds analogues to nostoclides containing the isopropyl group in position 4 of the lactone ring were synthesized in order to assess the impact of this in the biological activity. For the synthesis of these compounds, compound 3,4-dibromofuran-2(5H)-one was used as starting material. This compound in the presence of isopropyl magnesium bromide, copper iodide and chloride trimethylsilane, led to the synthesis of compound 3-bromo-4-isopropylfuran-2(5H)-one, with 48% yield. The reaction conditions for the synthesis of this compound were optimized. Yields were calculated by the Internal Standard Method using gas chromatography. The compound 3-benzyl-4-isopropylfuran-2(5H)-one, reagent used in the synthesis of analogues to nostoclides, was synthesized from the lactone 3-bromo-4-isopropylfuran-2 (5H)-one by Negishi coupling, using Pd(PPh)4 in DMF:THF/1:1, this compound was obtained with 36% yield. Subsequently, the substance 3-benzyl-4-isopropylfuran-2 (5H)-one was subjected to alkylidenation reactions with differently substituted aromatic aldehydes. Reactions were performed in the presence of diisopropylethylamine (DIPEA) and trifluoromethanesulfonate of tert-butyldimethylsilile (TBDMSOTf), at room temperature. The aldol intermediate obtained were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under reflux conditions, which resulted in 5 analogues nostoclides substances, with yields ranging from 22-86%. New γ-alkylidenebutenolides belonging to the class of 3,4-dihalo-5-arylidenefuran-2(5H)-ones were prepared from the lactones 3,4-dihalofuran-2(5H)-ones and different aromatic aldehydes by alkylidenation reaction already mentioned. Compounds analogues to nostoclides as 3,4-dihalo-5-arylidenefuran-2(5H)-ones and several lactones precursors were evaluated in vitro for their ability to inhibit the growth of three species of bacteria, E. coli, S. aureus and B. cereus, testing by disk-diffusion. Analogues to nostoclides tested showed no inhibition to none of the bacteria tested. The compounds belonging to the class of 3,4-dihalo-5-arylidenefuran-2 (5H)-ones and lactones 3,4-dibromofuran-2(5H)-one and 3,4-dichlorofuran-2(5H)-one showed inhibition against the different bacteria and they are considered potential antimicrobial agents.Os nostoclídeos são substâncias naturais isolados de uma alga verdeazul, Nostoc sp., encontrada em um líquen denominado Peltigera canina. Eles pertencem à classe de compostos conhecidos como γ-alquilidenobutenolídeos. Os nostoclídeos vêm sendo utilizados como compostos-modelo objetivando a descoberta de novos herbicidas. Compostos do tipo 3-benzil-5-arilidenofuran-2-(5H)-onas, análogos aos nostoclídeos, desprovidos do grupo isopropila, foram sintetizados, e a atividade fitotóxica dessas substâncais foi avaliada in vitro quanto à sua capacidade de interferir no transporte de elétrons, dirigido pela luz da água para o oxidante não-biológico ferricianeto de potássio. Para esse experimento, foram usados cloroplastos isolados de espinafre (Spinacia oleracea). No presente trabalho, foram buscados um entendimento dos diferentes parâmetros envolvidos na correlação entre estrutura química de diferentes análogos aos nostoclídeos já descritos na literatura bem como sua atividade biológica (capacidade dos análogos de interferirem com o transporte de elétrons em cloroplastos isolados de espinafre). Para tal propósito, foi usado o software CODESSA (COmprehensive DEscriptores for Structural and Statistical Analysis). Foram desenvolvidos dois modelos matemáticos, e, em ambos os modelos, o descritor de maior significância estatística selecionado foi o Image of the Onasager-Kirkwood solvation energy (SEOK), que relaciona de forma indireta a atividade fitotóxica com a polaridade das moléculas. Na presente pesquisa, compostos análogos aos nostoclídeos contendo o grupo isopropila na posição 4 do anel lactônico foram sintetizados, a fim de avaliar o seu impacto na atividade biológica. Para a síntese desses compostos, o composto 3,4-dibromofuran-2(5H)-ona foi utilizado como material de partida. Esse composto, na presença de brometo de isopropil magnésio, iodeto de cobre e cloreto de trimetilsilano, propiciou a síntese do composto 3-bromo-4- isopropilfuran-2(5H)-ona, com 48% de rendimento. As condições reacionais para a síntese do referido composto foram otimizadas. Os rendimentos foram calculados pelo Método do Padrão Interno utilizando cromatografia gasosa. O composto 3-benzil-4-isopropilfuran-2(5H)-ona, reagente usado na síntese dos análogos aos nostoclídeos, foi sintetizado, a partir da lactona 3-bromo-4-isopropilfuran-2(5H)-ona, pelo acoplamento de Negishi, utilizando-se o Pd(PPh)4 em DMF:THF/1:1, tendo sido o referido composto obtido com 36% de rendimento. Posteriormente, a substância 3-benzil-4-isopropilfuran-2(5H)-ona foi submetida a reações de alquilidenação com aldeídos aromáticos diferentemente substituídos. As reações foram realizadas na presença de diisopropiletilamina (DIPEA) e trifluorometanossulfonato de tert-butildimetilsilila (TBDMSOTf), em temperatura ambiente. Os intermediários aldólicos obtidos foram tratados com 1,8-diazabiciclo[5.4.0]undec-7-eno (DBU) sob condições de refluxo, resultando na obtenção de 5 substâncias análogas aos nostoclídeos, com rendimentos variando de 22-86%. Novos γ-alquilidenobutenolídeos pertencentes à classe das 3,4-dialo-5-arilidenofuran-2(5H)-onas foram preparados a partir das lactonas 3,4-dialofuran-2(5H)-onas e diferentes aldeídos aromáticos pela reação de alquilidenação já mencionada. Compostos análogos aos nostoclídeos, as 3,4-dialo-5-arilidenofuran-2(5H)-onas e diversas lactonas precursoras, foram avaliados in vitro quanto à capacidade em inibir o crescimento de três espécies de bactérias, E. coli, S. aureus e B. cereus, pelo teste de disco-difusão. Os análogos aos nostoclídeos testados não apresentaram inibição frente a nenhuma das bactérias testadas. Os compostos pertencentes à classe das 3,4-dialo-5-arilidenofuran-2(5H)-onas e as lactonas 3,4-dibromofuran-2(5H)-ona e 3,4-diclorofuran-2(5H)-ona apresentaram inibição frente às distintas bactérias, sendo considerados potenciais agentes antimicrobianos.Fundação de Amparo a Pesquisa do Estado de Minas Geraisapplication/pdfporUniversidade Federal de ViçosaDoutorado em AgroquímicaUFVBRAgroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânicaNostoclídeosQSARγ-alquilidenobutenolídeosAcoplamento de Neguishi3,4-dihaloarilidenofuran-2(5H)-onasNostoclidesQSARγ-alkylidenebutenolidescoupling Neguishi3,4-dihaloarylidenefuran-2(5H)-oneCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAEstudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeosStudy of the quantitative relationship chemical structurebiological activity of analogous compounds to nostoclides and synthesis of new γ-alkylidenebutenolidesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALtexto completo.pdfapplication/pdf1539113https://locus.ufv.br//bitstream/123456789/207/1/texto%20completo.pdf80d71a03cb299c5ee58a2b5d480df1c6MD51TEXTtexto completo.pdf.txttexto completo.pdf.txtExtracted texttext/plain267068https://locus.ufv.br//bitstream/123456789/207/2/texto%20completo.pdf.txtc0900f21d2ba43ab855ee615955f0fc2MD52THUMBNAILtexto completo.pdf.jpgtexto completo.pdf.jpgIM Thumbnailimage/jpeg3596https://locus.ufv.br//bitstream/123456789/207/3/texto%20completo.pdf.jpg843c4cfa3a77bdcf72875a78f56738e2MD53123456789/2072017-10-06 15:33:58.654oai:locus.ufv.br:123456789/207Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452017-10-06T18:33:58LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.por.fl_str_mv Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
dc.title.alternative.eng.fl_str_mv Study of the quantitative relationship chemical structurebiological activity of analogous compounds to nostoclides and synthesis of new γ-alkylidenebutenolides
title Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
spellingShingle Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
Pinheiro, Patrícia Fontes
Nostoclídeos
QSAR
γ-alquilidenobutenolídeos
Acoplamento de Neguishi
3,4-dihaloarilidenofuran-2(5H)-onas
Nostoclides
QSAR
γ-alkylidenebutenolides
coupling Neguishi
3,4-dihaloarylidenefuran-2(5H)-one
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
title_short Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
title_full Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
title_fullStr Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
title_full_unstemmed Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
title_sort Estudo da relação quantitativa estrutura química-atividade biológica de compostos análogos aos nostoclídeos e síntese de novos γ-alquilidenobutenolídeos
author Pinheiro, Patrícia Fontes
author_facet Pinheiro, Patrícia Fontes
author_role author
dc.contributor.authorLattes.por.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4223016U2
dc.contributor.author.fl_str_mv Pinheiro, Patrícia Fontes
dc.contributor.advisor-co1.fl_str_mv Maltha, Célia Regina álvares
dc.contributor.advisor-co1Lattes.fl_str_mv http://lattes.cnpq.br/7346715444030145
dc.contributor.advisor-co2.fl_str_mv Demuner, Antônio Jacinto
dc.contributor.advisor-co2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783217D3
dc.contributor.advisor1.fl_str_mv Barbosa, Luiz Claudio de Almeida
dc.contributor.advisor1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2
dc.contributor.referee1.fl_str_mv Fernandes, Sergio Antônio
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4760152Y5
dc.contributor.referee2.fl_str_mv Gil, Laurent Frederic
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/6301871767422750
dc.contributor.referee3.fl_str_mv Conceição, Gelson José Andrade da
dc.contributor.referee3Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723800Z8
contributor_str_mv Maltha, Célia Regina álvares
Demuner, Antônio Jacinto
Barbosa, Luiz Claudio de Almeida
Fernandes, Sergio Antônio
Gil, Laurent Frederic
Conceição, Gelson José Andrade da
dc.subject.por.fl_str_mv Nostoclídeos
QSAR
γ-alquilidenobutenolídeos
Acoplamento de Neguishi
3,4-dihaloarilidenofuran-2(5H)-onas
topic Nostoclídeos
QSAR
γ-alquilidenobutenolídeos
Acoplamento de Neguishi
3,4-dihaloarilidenofuran-2(5H)-onas
Nostoclides
QSAR
γ-alkylidenebutenolides
coupling Neguishi
3,4-dihaloarylidenefuran-2(5H)-one
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
dc.subject.eng.fl_str_mv Nostoclides
QSAR
γ-alkylidenebutenolides
coupling Neguishi
3,4-dihaloarylidenefuran-2(5H)-one
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
description Nostoclides are natural substances isolated from blue-green seaweed, Nostoc sp., found in a lichen called Peltigera canina. They belong to the class of compounds known as γ-alkylidenebutenolides. Nostoclides have been used as model compounds aimed the discovery of new herbicides. Compounds 3-benzyl-5-arylidenefuran-2-(5H)-ones, analogues to nostoclides devoid of the isopropyl group were synthesized and phytotoxicity of these compounds was evaluated in vitro for their ability to interfere in electron transport directed by light, water to the non-biological oxidant potassium ferricyanide. For this experiment were used chloroplasts isolated from spinach (Spinacia oleracea). In this study, we look for an understanding of the different parameters involved in the correlation between chemical structure of different analogues nostoclides to those described in the literature and biological activity (ability of analogues to interfere with electron transport in chloroplasts isolated from spinach) of these compounds. For this purpose, we used the software CODESSA (COmprehensive DEscriptors for Structural and Statistical Analysis). We developed two mathematical models, in both models, the descriptor of greater significance was selected 'Image of the Onasager-Kirkwood solvation energy' (SEOK), which relates indirectly to phytotoxicity with the polarity of the molecules. In the present investigation, compounds analogues to nostoclides containing the isopropyl group in position 4 of the lactone ring were synthesized in order to assess the impact of this in the biological activity. For the synthesis of these compounds, compound 3,4-dibromofuran-2(5H)-one was used as starting material. This compound in the presence of isopropyl magnesium bromide, copper iodide and chloride trimethylsilane, led to the synthesis of compound 3-bromo-4-isopropylfuran-2(5H)-one, with 48% yield. The reaction conditions for the synthesis of this compound were optimized. Yields were calculated by the Internal Standard Method using gas chromatography. The compound 3-benzyl-4-isopropylfuran-2(5H)-one, reagent used in the synthesis of analogues to nostoclides, was synthesized from the lactone 3-bromo-4-isopropylfuran-2 (5H)-one by Negishi coupling, using Pd(PPh)4 in DMF:THF/1:1, this compound was obtained with 36% yield. Subsequently, the substance 3-benzyl-4-isopropylfuran-2 (5H)-one was subjected to alkylidenation reactions with differently substituted aromatic aldehydes. Reactions were performed in the presence of diisopropylethylamine (DIPEA) and trifluoromethanesulfonate of tert-butyldimethylsilile (TBDMSOTf), at room temperature. The aldol intermediate obtained were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under reflux conditions, which resulted in 5 analogues nostoclides substances, with yields ranging from 22-86%. New γ-alkylidenebutenolides belonging to the class of 3,4-dihalo-5-arylidenefuran-2(5H)-ones were prepared from the lactones 3,4-dihalofuran-2(5H)-ones and different aromatic aldehydes by alkylidenation reaction already mentioned. Compounds analogues to nostoclides as 3,4-dihalo-5-arylidenefuran-2(5H)-ones and several lactones precursors were evaluated in vitro for their ability to inhibit the growth of three species of bacteria, E. coli, S. aureus and B. cereus, testing by disk-diffusion. Analogues to nostoclides tested showed no inhibition to none of the bacteria tested. The compounds belonging to the class of 3,4-dihalo-5-arylidenefuran-2 (5H)-ones and lactones 3,4-dibromofuran-2(5H)-one and 3,4-dichlorofuran-2(5H)-one showed inhibition against the different bacteria and they are considered potential antimicrobial agents.
publishDate 2009
dc.date.issued.fl_str_mv 2009-10-19
dc.date.available.fl_str_mv 2011-06-06
2015-03-26T12:05:56Z
dc.date.accessioned.fl_str_mv 2015-03-26T12:05:56Z
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dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
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dc.identifier.citation.fl_str_mv PINHEIRO, Patrícia Fontes. Study of the quantitative relationship chemical structurebiological activity of analogous compounds to nostoclides and synthesis of new γ-alkylidenebutenolides. 2009. 186 f. Tese (Doutorado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2009.
dc.identifier.uri.fl_str_mv http://locus.ufv.br/handle/123456789/207
identifier_str_mv PINHEIRO, Patrícia Fontes. Study of the quantitative relationship chemical structurebiological activity of analogous compounds to nostoclides and synthesis of new γ-alkylidenebutenolides. 2009. 186 f. Tese (Doutorado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2009.
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dc.publisher.country.fl_str_mv BR
dc.publisher.department.fl_str_mv Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica
publisher.none.fl_str_mv Universidade Federal de Viçosa
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