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

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Main Author:	Zampirolli, Leticia Silotti
Other Authors:	Costa, Jo?o Batista Neves da
Format:	Others
Language:	Portuguese
Published:	Universidade Federal Rural do Rio de Janeiro 2017
Subjects:	dialkylphosphorylhydrazones phosphorohydrazidic acid biological activity isatin Dialquilfosforilidrazonas ?cido fosforoidraz?dico atividade biol?gica isatina Ci?ncias Exatas e da Terra
Online Access:	https://tede.ufrrj.br/jspui/handle/jspui/2077

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record_format	oai_dc
collection	NDLTD
language	Portuguese
format	Others
sources	NDLTD
topic	dialkylphosphorylhydrazones phosphorohydrazidic acid biological activity isatin Dialquilfosforilidrazonas ?cido fosforoidraz?dico atividade biol?gica isatina Ci?ncias Exatas e da Terra
spellingShingle	dialkylphosphorylhydrazones phosphorohydrazidic acid biological activity isatin Dialquilfosforilidrazonas ?cido fosforoidraz?dico atividade biol?gica isatina Ci?ncias Exatas e da Terra Zampirolli, Leticia Silotti Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
description	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: 2009-05-27 === Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil. === 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. === 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.
author2	Costa, Jo?o Batista Neves da
author_facet	Costa, Jo?o Batista Neves da Zampirolli, Leticia Silotti
author	Zampirolli, Leticia Silotti
author_sort	Zampirolli, Leticia Silotti
title	Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica
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
publisher	Universidade Federal Rural do Rio de Janeiro
publishDate	2017
url	https://tede.ufrrj.br/jspui/handle/jspui/2077
work_keys_str_mv	AT zampirollileticiasilotti dialquilfosforilidrazonasderivadasdeisatinasnsubstitudascompotencialatividadebiolgica AT zampirollileticiasilotti dialkylphosphorylhydrazonesderivedfromnsubstitutedisatinswithpotentialbiologicalactivity
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spelling	ndltd-IBICT-oai-localhost-jspui-20772019-01-22T00:51:03Z Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica Dialkylphosphorylhydrazones derived from Nsubstituted isatins with potential biological activity. Zampirolli, Leticia Silotti Costa, Jo?o Batista Neves da Marques, Monica Regina da Costa Bernardino, Alice Maria Rolim Rumjanek, Victor Marques dialkylphosphorylhydrazones phosphorohydrazidic acid biological activity isatin Dialquilfosforilidrazonas ?cido fosforoidraz?dico atividade biol?gica isatina Ci?ncias Exatas e da Terra 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: 2009-05-27 Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil. 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. 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. 2017-10-05T11:53:08Z 2009-05-27 info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/masterThesis Zampirolli, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substitu?das com potencial atividade biol?gica. 2009. [256 f.]. Disserta??o( PROGRAMA DE P?S-GRADUA??O EM QU?MICA) - Universidade Federal Rural do Rio de Janeiro, [Serop?dica - RJ] . https://tede.ufrrj.br/jspui/handle/jspui/2077 por AINSCOUGH, E.W.; BRODIE, A.M.; DOBBS, A.J.; RANFORD, J.D.; WATERS, J.M. 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