Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica

Detalhes bibliográficos
Ano de defesa: 2009
Autor(a) principal: Zampirolli, Leticia Silotti lattes
Orientador(a): Costa, Jo?o Batista Neves da lattes
Banca de defesa: Marques, Monica Regina da Costa, Bernardino, Alice Maria Rolim, Rumjanek, Victor Marques
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal Rural do Rio de Janeiro
Programa de Pós-Graduação: Programa de P?s-Gradua??o em Qu?mica
Departamento: Instituto de Ci?ncias Exatas
País: Brasil
Palavras-chave em Português:
Dialquilfosforilidrazonas
?cido fosforoidraz?dico
atividade biol?gica
isatina
Palavras-chave em Inglês:
dialkylphosphorylhydrazones
phosphorohydrazidic acid
biological activity
isatin
Área do conhecimento CNPq:
Qu?mica
Link de acesso: https://tede.ufrrj.br/jspui/handle/jspui/2077
Resumo: A series of new dialkylphosphorylhydrazones (phosphorohydrazidic acid, N?-[1,2-dihydro-2- oxo-(R1)-3H-indole-3-iliden]- dialkyl esters was synthesized and characterized by IR, 1H, 13C and 31P NMR and mass spectroscopy. These dialkylphosphorylhydrazones were synthesized in three steps. The first step involved the synthesis of different dialkylphosphites which are obtained by the reaction of PCl3 with three mols of the corresponding alcohols. The second step consisted of the reaction between the dialkylphosphites and hydrazine in a two phase system, leading to the formation of the dialkylphosphorylhydrazines. Finally, the last step was the condensation of these dialkylphosphorylhydrazines with different N-substituted isatins. The analysis of the 1H, 13C and 31P NMR spectra showed the existence of the two possible diastereoisomers E and Z for compounds 1, 2, 6, 10 and 12, while for the remaining compounds only the Z isomer is present. Ten of these compounds were preliminarily tested for their inhibition potential against two protozoa (Trypanosoma cruzi and Leishmania amazonensis). All compounds tested showed cell proliferation inhibition of 98% at 50 ?M for Leishmania amazonensis, whereas for T. cruzi, inhibition of epimastigote cell proliferation was found to be higher than 75% for all compounds tested except 6, which showed a 59% inhibition. These ten compounds were also evaluated against Plasmodium falciparum, affording inhibitions higher than 90% for a 1mM concentration. These compounds were also investigated for their fungicidal activity against phytopatogenic Rhizoctonia solani and Fusarium oxysporum. Compounds 9 and 11 showed a miscelial growth inhibition of 58% for Rhizoctonia solani while compound 12 afforde a 72% inhibition. Compounds 1, 2, 11 and 12 gave Fusarium oxysporum inhibition higher than 52%. Finally, the compounds synthesized were also evaluated for their inhibitory potential against lettuce seed germination and it was observed that the same compounds which showed fungicidal activity were not able to inhibit seed germination.
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spelling Costa, Jo?o Batista Neves da432..365107-49http://lattes.cnpq.br/8678051184959173Marques, Monica Regina da CostaBernardino, Alice Maria RolimRumjanek, Victor Marques107.202.247-80http://lattes.cnpq.br/0235373064063651Zampirolli, Leticia Silotti2017-10-05T11:53:08Z2009-05-27ZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica. 2009. 256 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009.https://tede.ufrrj.br/jspui/handle/jspui/2077A series of new dialkylphosphorylhydrazones (phosphorohydrazidic acid, N?-[1,2-dihydro-2- oxo-(R1)-3H-indole-3-iliden]- dialkyl esters was synthesized and characterized by IR, 1H, 13C and 31P NMR and mass spectroscopy. These dialkylphosphorylhydrazones were synthesized in three steps. The first step involved the synthesis of different dialkylphosphites which are obtained by the reaction of PCl3 with three mols of the corresponding alcohols. The second step consisted of the reaction between the dialkylphosphites and hydrazine in a two phase system, leading to the formation of the dialkylphosphorylhydrazines. Finally, the last step was the condensation of these dialkylphosphorylhydrazines with different N-substituted isatins. The analysis of the 1H, 13C and 31P NMR spectra showed the existence of the two possible diastereoisomers E and Z for compounds 1, 2, 6, 10 and 12, while for the remaining compounds only the Z isomer is present. Ten of these compounds were preliminarily tested for their inhibition potential against two protozoa (Trypanosoma cruzi and Leishmania amazonensis). All compounds tested showed cell proliferation inhibition of 98% at 50 ?M for Leishmania amazonensis, whereas for T. cruzi, inhibition of epimastigote cell proliferation was found to be higher than 75% for all compounds tested except 6, which showed a 59% inhibition. These ten compounds were also evaluated against Plasmodium falciparum, affording inhibitions higher than 90% for a 1mM concentration. These compounds were also investigated for their fungicidal activity against phytopatogenic Rhizoctonia solani and Fusarium oxysporum. Compounds 9 and 11 showed a miscelial growth inhibition of 58% for Rhizoctonia solani while compound 12 afforde a 72% inhibition. Compounds 1, 2, 11 and 12 gave Fusarium oxysporum inhibition higher than 52%. Finally, the compounds synthesized were also evaluated for their inhibitory potential against lettuce seed germination and it was observed that the same compounds which showed fungicidal activity were not able to inhibit seed germination.Uma s?rie de 16 dialquilfosforilidrazonas (?cido fosforoidraz?dico, N? -[1,2-diidro-2-oxo-(R1)- 3H- indol-3-ilideno] -, ?ster de dialquila), sendo todas in?ditas, foram sintetizadas e caracterizadas pelas t?cnicas de espectrometria de IV, RMN de 1H, RMN de 13C, RMN de 31P e massas. As novas dialquilfosforilidrazonas foram sintetizadas em tr?s etapas de rea??o. A primeira etapa consistiu na s?ntese de diferentes fosfitos de dialquila que foram obtidos atrav?s da rea??o do tricloreto de f?sforo (PCl3) com tr?s mols do ?lcool correspondente. Na segunda etapa, a rea??o dos fosfitos de dialquila com a hidrazina, em um sistema bif?sico, levou ? forma??o das dialquilfosforilidrazinas. A ?ltima etapa foi a condensa??o destas dialquilfosforilidrazinas com diferentes isatinas substitu?das. A an?lise dos espectros de RMN de 1H, RMN de 13C, RMN de 31P das dialquilfosforilidrazonas mostraram a coexist?ncia dos dois poss?veis diastereois?meros E e Z, para os compostos 1, 2, 6, 10 e 12, enquanto que para os compostos restantes observou-se apenas o diastereois?mero Z. Dos compostos sintetizados, dez foram avaliados preliminarmente quanto ao potencial inibit?rio de prolifera??o de dois protozo?rios (Trypanosoma cruzi e Leishmania amazonensis). Para Leishmania amazonensis todos os compostos testados apresentaram inibi??o da prolifera??o celular de 98 % a 50 ?M. Enquanto que para T.cruzi verificou-se inibi??o da prolifera??o celular de epimastigotas superior a 75% para todos compostos testados, a exce??o do composto (6) cuja inibi??o foi de 59 %. Esses dez compostos tamb?m foram avaliados frente ao protozo?rio Plasmodium falciparum apresentando inibi??o superior a 90 % para todos os compostos testados, a uma concentra??o de 1mM. Essas dialquilfosforilidrazonas tamb?m tiveram a a??o fungicida avaliada frente aos fungos fitopatog?nicos (Rhizoctonia solani e Fusarium oxysporum). Em Rhizoctonia solani os compostos (9) e (11) apresentaram inibi??o do crescimento miscelial de 58 %, j? o composto (12) apresentou inibi??o de 72%. Para o Fusarium oxysporum destacaram-se os compostos (1, 2, 11 e 12) com inibi??o superior a 52 %. Esses compostos tamb?m foram avaliados quanto ao potencial inibit?rio de germina??o em sementes de alface e verificouse que os mesmos compostos que apresentaram efeitos fungist?ticos, n?o inibiram a germina??o de sementes de alface.Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2017-10-05T11:53:08Z No. of bitstreams: 1 2009 - Leticia Silotti Zampirolli.pdf: 25893124 bytes, checksum: bd44115917dd331e511dc65cd22738a1 (MD5)Made available in DSpace on 2017-10-05T11:53:08Z (GMT). No. of bitstreams: 1 2009 - Leticia Silotti Zampirolli.pdf: 25893124 bytes, checksum: bd44115917dd331e511dc65cd22738a1 (MD5) Previous issue date: 2009-05-27Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil.application/pdfhttps://tede.ufrrj.br/retrieve/5999/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/15270/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/21788/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/28172/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/34550/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/40938/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/47294/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpghttps://tede.ufrrj.br/retrieve/53716/2009%20-%20Leticia%20Silotti%20Zampirolli.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias ExatasAINSCOUGH, E.W.; BRODIE, A.M.; DOBBS, A.J.; RANFORD, J.D.; WATERS, J.M. 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dc.title.por.fl_str_mv Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
dc.title.alternative.eng.fl_str_mv Dialkylphosphorylhydrazones derived from N substituted isatins with potential biological activity
title Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
spellingShingle Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
Zampirolli, Leticia Silotti
dialkylphosphorylhydrazones
phosphorohydrazidic acid
biological activity
isatin
Dialquilfosforilidrazonas
?cido fosforoidraz?dico
atividade biol?gica
isatina
Qu?mica
title_short Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
title_full Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
title_fullStr Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
title_full_unstemmed Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
title_sort Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
author Zampirolli, Leticia Silotti
author_facet Zampirolli, Leticia Silotti
author_role author
dc.contributor.advisor1.fl_str_mv Costa, Jo?o Batista Neves da
dc.contributor.advisor1ID.fl_str_mv 432..365107-49
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/8678051184959173
dc.contributor.referee1.fl_str_mv Marques, Monica Regina da Costa
dc.contributor.referee2.fl_str_mv Bernardino, Alice Maria Rolim
dc.contributor.referee3.fl_str_mv Rumjanek, Victor Marques
dc.contributor.authorID.fl_str_mv 107.202.247-80
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/0235373064063651
dc.contributor.author.fl_str_mv Zampirolli, Leticia Silotti
contributor_str_mv Costa, Jo?o Batista Neves da
Marques, Monica Regina da Costa
Bernardino, Alice Maria Rolim
Rumjanek, Victor Marques
dc.subject.eng.fl_str_mv dialkylphosphorylhydrazones
phosphorohydrazidic acid
biological activity
isatin
topic dialkylphosphorylhydrazones
phosphorohydrazidic acid
biological activity
isatin
Dialquilfosforilidrazonas
?cido fosforoidraz?dico
atividade biol?gica
isatina
Qu?mica
dc.subject.por.fl_str_mv Dialquilfosforilidrazonas
?cido fosforoidraz?dico
atividade biol?gica
isatina
dc.subject.cnpq.fl_str_mv Qu?mica
description A series of new dialkylphosphorylhydrazones (phosphorohydrazidic acid, N?-[1,2-dihydro-2- oxo-(R1)-3H-indole-3-iliden]- dialkyl esters was synthesized and characterized by IR, 1H, 13C and 31P NMR and mass spectroscopy. These dialkylphosphorylhydrazones were synthesized in three steps. The first step involved the synthesis of different dialkylphosphites which are obtained by the reaction of PCl3 with three mols of the corresponding alcohols. The second step consisted of the reaction between the dialkylphosphites and hydrazine in a two phase system, leading to the formation of the dialkylphosphorylhydrazines. Finally, the last step was the condensation of these dialkylphosphorylhydrazines with different N-substituted isatins. The analysis of the 1H, 13C and 31P NMR spectra showed the existence of the two possible diastereoisomers E and Z for compounds 1, 2, 6, 10 and 12, while for the remaining compounds only the Z isomer is present. Ten of these compounds were preliminarily tested for their inhibition potential against two protozoa (Trypanosoma cruzi and Leishmania amazonensis). All compounds tested showed cell proliferation inhibition of 98% at 50 ?M for Leishmania amazonensis, whereas for T. cruzi, inhibition of epimastigote cell proliferation was found to be higher than 75% for all compounds tested except 6, which showed a 59% inhibition. These ten compounds were also evaluated against Plasmodium falciparum, affording inhibitions higher than 90% for a 1mM concentration. These compounds were also investigated for their fungicidal activity against phytopatogenic Rhizoctonia solani and Fusarium oxysporum. Compounds 9 and 11 showed a miscelial growth inhibition of 58% for Rhizoctonia solani while compound 12 afforde a 72% inhibition. Compounds 1, 2, 11 and 12 gave Fusarium oxysporum inhibition higher than 52%. Finally, the compounds synthesized were also evaluated for their inhibitory potential against lettuce seed germination and it was observed that the same compounds which showed fungicidal activity were not able to inhibit seed germination.
publishDate 2009
dc.date.issued.fl_str_mv 2009-05-27
dc.date.accessioned.fl_str_mv 2017-10-05T11:53:08Z
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.citation.fl_str_mv ZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica. 2009. 256 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009.
dc.identifier.uri.fl_str_mv https://tede.ufrrj.br/jspui/handle/jspui/2077
identifier_str_mv ZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica. 2009. 256 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2009.
url https://tede.ufrrj.br/jspui/handle/jspui/2077
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