Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica
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| Data de Publicação: | 2009 |
| Tipo de documento: | Dissertação |
| Idioma: | por |
| Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
| Texto Completo: | https://rima.ufrrj.br/jspui/handle/20.500.14407/14673 |
Resumo: | Uma série de 16 dialquilfosforilidrazonas (ácido fosforoidrazídico, N’ -[1,2-diidro-2-oxo-(R1)- 3H- indol-3-ilideno] -, éster de dialquila), sendo todas inéditas, foram sintetizadas e caracterizadas pelas técnicas de espectrometria de IV, RMN de 1H, RMN de 13C, RMN de 31P e massas. As novas dialquilfosforilidrazonas foram sintetizadas em três etapas de reação. A primeira etapa consistiu na síntese de diferentes fosfitos de dialquila que foram obtidos através da reação do tricloreto de fósforo (PCl3) com três mols do álcool correspondente. Na segunda etapa, a reação dos fosfitos de dialquila com a hidrazina, em um sistema bifásico, levou á formação das dialquilfosforilidrazinas. A última etapa foi a condensação destas dialquilfosforilidrazinas com diferentes isatinas substituídas. A análise dos espectros de RMN de 1H, RMN de 13C, RMN de 31P das dialquilfosforilidrazonas mostraram a coexistência dos dois possíveis diastereoisômeros E e Z, para os compostos 1, 2, 6, 10 e 12, enquanto que para os compostos restantes observou-se apenas o diastereoisômero Z. Dos compostos sintetizados, dez foram avaliados preliminarmente quanto ao potencial inibitório de proliferação de dois protozoários (Trypanosoma cruzi e Leishmania amazonensis). Para Leishmania amazonensis todos os compostos testados apresentaram inibição da proliferação celular de 98 % a 50 μM. Enquanto que para T.cruzi verificou-se inibição da proliferação celular de epimastigotas superior a 75% para todos compostos testados, a exceção do composto (6) cuja inibição foi de 59 %. Esses dez compostos também foram avaliados frente ao protozoário Plasmodium falciparum apresentando inibição superior a 90 % para todos os compostos testados, a uma concentração de 1mM. Essas dialquilfosforilidrazonas também tiveram a ação fungicida avaliada frente aos fungos fitopatogênicos (Rhizoctonia solani e Fusarium oxysporum). Em Rhizoctonia solani os compostos (9) e (11) apresentaram inibição do crescimento miscelial de 58 %, já o composto (12) apresentou inibição de 72%. Para o Fusarium oxysporum destacaram-se os compostos (1, 2, 11 e 12) com inibição superior a 52 %. Esses compostos também foram avaliados quanto ao potencial inibitório de germinação em sementes de alface e verificouse que os mesmos compostos que apresentaram efeitos fungistáticos, não inibiram a germinação de sementes de alface. |
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Zampirolli, Leticia SilottiCosta, João Batista Neves da432..365107-49http://lattes.cnpq.br/8678051184959173Marques, Monica Regina da CostaBernardino, Alice Maria RolimRumjanek, Victor Marques107.202.247-80http://lattes.cnpq.br/02353730640636512023-12-22T03:04:20Z2023-12-22T03:04:20Z2009-05-27ZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica. 2009. 256 f. Dissertação (Mestrado em Química) - Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica - RJ, 2009.https://rima.ufrrj.br/jspui/handle/20.500.14407/14673Uma série de 16 dialquilfosforilidrazonas (ácido fosforoidrazídico, N’ -[1,2-diidro-2-oxo-(R1)- 3H- indol-3-ilideno] -, éster de dialquila), sendo todas inéditas, foram sintetizadas e caracterizadas pelas técnicas de espectrometria de IV, RMN de 1H, RMN de 13C, RMN de 31P e massas. As novas dialquilfosforilidrazonas foram sintetizadas em três etapas de reação. A primeira etapa consistiu na síntese de diferentes fosfitos de dialquila que foram obtidos através da reação do tricloreto de fósforo (PCl3) com três mols do álcool correspondente. Na segunda etapa, a reação dos fosfitos de dialquila com a hidrazina, em um sistema bifásico, levou á formação das dialquilfosforilidrazinas. A última etapa foi a condensação destas dialquilfosforilidrazinas com diferentes isatinas substituídas. A análise dos espectros de RMN de 1H, RMN de 13C, RMN de 31P das dialquilfosforilidrazonas mostraram a coexistência dos dois possíveis diastereoisômeros E e Z, para os compostos 1, 2, 6, 10 e 12, enquanto que para os compostos restantes observou-se apenas o diastereoisômero Z. Dos compostos sintetizados, dez foram avaliados preliminarmente quanto ao potencial inibitório de proliferação de dois protozoários (Trypanosoma cruzi e Leishmania amazonensis). Para Leishmania amazonensis todos os compostos testados apresentaram inibição da proliferação celular de 98 % a 50 μM. Enquanto que para T.cruzi verificou-se inibição da proliferação celular de epimastigotas superior a 75% para todos compostos testados, a exceção do composto (6) cuja inibição foi de 59 %. Esses dez compostos também foram avaliados frente ao protozoário Plasmodium falciparum apresentando inibição superior a 90 % para todos os compostos testados, a uma concentração de 1mM. Essas dialquilfosforilidrazonas também tiveram a ação fungicida avaliada frente aos fungos fitopatogênicos (Rhizoctonia solani e Fusarium oxysporum). Em Rhizoctonia solani os compostos (9) e (11) apresentaram inibição do crescimento miscelial de 58 %, já o composto (12) apresentou inibição de 72%. Para o Fusarium oxysporum destacaram-se os compostos (1, 2, 11 e 12) com inibição superior a 52 %. Esses compostos também foram avaliados quanto ao potencial inibitório de germinação em sementes de alface e verificouse que os mesmos compostos que apresentaram efeitos fungistáticos, não inibiram a germinação de sementes de alface.Coordenação de Aperfeiçoamento de Pessoal de Nível 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 μM 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.application/pdfporUniversidade Federal Rural do Rio de JaneiroPrograma de Pós-Graduação em QuímicaUFRRJBrasilInstituto de Ciências Exatasdialkylphosphorylhydrazonesphosphorohydrazidic acidbiological activityisatinDialquilfosforilidrazonasácido fosforoidrazídicoatividade biológicaisatinaQuímicaDialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológicaDialkylphosphorylhydrazones derived from N substituted isatins with potential biological activityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisAINSCOUGH, 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 - substituídas com potencial atividade biológica |
| dc.title.alternative.eng.fl_str_mv |
Dialkylphosphorylhydrazones derived from N substituted isatins with potential biological activity |
| title |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| spellingShingle |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica Zampirolli, Leticia Silotti dialkylphosphorylhydrazones phosphorohydrazidic acid biological activity isatin Dialquilfosforilidrazonas ácido fosforoidrazídico atividade biológica isatina Química |
| title_short |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| title_full |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| title_fullStr |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| title_full_unstemmed |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| title_sort |
Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica |
| author |
Zampirolli, Leticia Silotti |
| author_facet |
Zampirolli, Leticia Silotti |
| author_role |
author |
| dc.contributor.author.fl_str_mv |
Zampirolli, Leticia Silotti |
| dc.contributor.advisor1.fl_str_mv |
Costa, João 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 |
| contributor_str_mv |
Costa, João 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 ácido fosforoidrazídico atividade biológica isatina Química |
| dc.subject.por.fl_str_mv |
Dialquilfosforilidrazonas ácido fosforoidrazídico atividade biológica isatina |
| dc.subject.cnpq.fl_str_mv |
Química |
| description |
Uma série de 16 dialquilfosforilidrazonas (ácido fosforoidrazídico, N’ -[1,2-diidro-2-oxo-(R1)- 3H- indol-3-ilideno] -, éster de dialquila), sendo todas inéditas, foram sintetizadas e caracterizadas pelas técnicas de espectrometria de IV, RMN de 1H, RMN de 13C, RMN de 31P e massas. As novas dialquilfosforilidrazonas foram sintetizadas em três etapas de reação. A primeira etapa consistiu na síntese de diferentes fosfitos de dialquila que foram obtidos através da reação do tricloreto de fósforo (PCl3) com três mols do álcool correspondente. Na segunda etapa, a reação dos fosfitos de dialquila com a hidrazina, em um sistema bifásico, levou á formação das dialquilfosforilidrazinas. A última etapa foi a condensação destas dialquilfosforilidrazinas com diferentes isatinas substituídas. A análise dos espectros de RMN de 1H, RMN de 13C, RMN de 31P das dialquilfosforilidrazonas mostraram a coexistência dos dois possíveis diastereoisômeros E e Z, para os compostos 1, 2, 6, 10 e 12, enquanto que para os compostos restantes observou-se apenas o diastereoisômero Z. Dos compostos sintetizados, dez foram avaliados preliminarmente quanto ao potencial inibitório de proliferação de dois protozoários (Trypanosoma cruzi e Leishmania amazonensis). Para Leishmania amazonensis todos os compostos testados apresentaram inibição da proliferação celular de 98 % a 50 μM. Enquanto que para T.cruzi verificou-se inibição da proliferação celular de epimastigotas superior a 75% para todos compostos testados, a exceção do composto (6) cuja inibição foi de 59 %. Esses dez compostos também foram avaliados frente ao protozoário Plasmodium falciparum apresentando inibição superior a 90 % para todos os compostos testados, a uma concentração de 1mM. Essas dialquilfosforilidrazonas também tiveram a ação fungicida avaliada frente aos fungos fitopatogênicos (Rhizoctonia solani e Fusarium oxysporum). Em Rhizoctonia solani os compostos (9) e (11) apresentaram inibição do crescimento miscelial de 58 %, já o composto (12) apresentou inibição de 72%. Para o Fusarium oxysporum destacaram-se os compostos (1, 2, 11 e 12) com inibição superior a 52 %. Esses compostos também foram avaliados quanto ao potencial inibitório de germinação em sementes de alface e verificouse que os mesmos compostos que apresentaram efeitos fungistáticos, não inibiram a germinação de sementes de alface. |
| publishDate |
2009 |
| dc.date.issued.fl_str_mv |
2009-05-27 |
| dc.date.accessioned.fl_str_mv |
2023-12-22T03:04:20Z |
| dc.date.available.fl_str_mv |
2023-12-22T03:04:20Z |
| 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 - substituídas com potencial atividade biológica. 2009. 256 f. Dissertação (Mestrado em Química) - Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica - RJ, 2009. |
| dc.identifier.uri.fl_str_mv |
https://rima.ufrrj.br/jspui/handle/20.500.14407/14673 |
| identifier_str_mv |
ZAMPIROLLI, Leticia Silotti. Dialquilfosforilidrazonas derivadas de isatinas N - substituídas com potencial atividade biológica. 2009. 256 f. Dissertação (Mestrado em Química) - Instituto de Ciências Exatas, Universidade Federal Rural do Rio de Janeiro, Seropédica - RJ, 2009. |
| url |
https://rima.ufrrj.br/jspui/handle/20.500.14407/14673 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.references.por.fl_str_mv |
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