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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.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/2077 |
| Date | 27 May 2009 |
| Creators | Zampirolli, Leticia Silotti |
| Contributors | Costa, Jo?o Batista Neves da, Marques, Monica Regina da Costa, Bernardino, Alice Maria Rolim, Rumjanek, Victor Marques |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
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