RESUMO
Stable Schiff bases containing a furoxan moiety are synthesized as single regioisomers by the reaction of 3-methyl-2-oxy-furazan-4-carbaldehydewith various amino compounds at room temperature. The structures of synthesized compounds were fully characterized by multinuclear NMR spectroscopy and X-ray crystallography. The effect of synthesized Schiff bases containing a furoxan moiety on biological generation of reactive oxygen species and nitric oxide in plant tissues was investigated for the first time by fluorescence microscopy and the released NO identified as nitrite with Griess reagent. There is a good correlation between the biological generation of NO determined by fluorescence microscopy and with Griess reagent. Some of the synthesized compounds exhibited both nitric oxide and reactive oxygen species generation abilities and represent potential NO donors in plant tissues.
Assuntos
Aldeídos/síntese química , Arabidopsis/efeitos dos fármacos , Doadores de Óxido Nítrico/farmacologia , Oxidiazóis/farmacologia , Folhas de Planta/efeitos dos fármacos , Bases de Schiff/farmacologia , Aldeídos/farmacologia , Arabidopsis/química , Arabidopsis/metabolismo , Etilenodiaminas/química , Fluoresceínas/química , Corantes Fluorescentes/química , Microscopia de Fluorescência , Óxido Nítrico/agonistas , Óxido Nítrico/biossíntese , Doadores de Óxido Nítrico/síntese química , Nitritos/agonistas , Nitritos/metabolismo , Oxidiazóis/síntese química , Folhas de Planta/química , Folhas de Planta/metabolismo , Espécies Reativas de Oxigênio/agonistas , Espécies Reativas de Oxigênio/metabolismo , Bases de Schiff/síntese química , Plântula/química , Plântula/efeitos dos fármacos , Plântula/metabolismo , Sementes/crescimento & desenvolvimento , Estereoisomerismo , Sulfanilamidas/químicaRESUMO
The importance of strigolactones in plant biology prompted us to synthesize simplified strigolactone mimics effective as exogenous signals for rhizosphere organisms. New strigolactone mimics easily derived from simple and available starting materials in significant amounts were prepared and fully characterized. These compounds contain an aromatic or heterocyclic ring, usually present in various bioactive molecules, connected by an ether link to a furan-2-one moiety. The new synthesized strigolactone mimics were confirmed to be active on plant pathogenic fungi and parasitic weed seeds.
Assuntos
Ascomicetos/efeitos dos fármacos , Materiais Biomiméticos/síntese química , Lactonas/química , Plantas Daninhas/efeitos dos fármacos , Pirimidinas/síntese química , Rizosfera , Ascomicetos/crescimento & desenvolvimento , Materiais Biomiméticos/farmacologia , Fusarium/efeitos dos fármacos , Fusarium/crescimento & desenvolvimento , Germinação/efeitos dos fármacos , Lactonas/isolamento & purificação , Lactonas/farmacologia , Orobanchaceae/efeitos dos fármacos , Orobanchaceae/crescimento & desenvolvimento , Reguladores de Crescimento de Plantas/química , Reguladores de Crescimento de Plantas/isolamento & purificação , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Brotos de Planta/metabolismo , Plantas Daninhas/crescimento & desenvolvimento , Pirimidinas/farmacologia , Rhizoctonia/efeitos dos fármacos , Rhizoctonia/crescimento & desenvolvimento , Sementes/efeitos dos fármacos , Sementes/crescimento & desenvolvimentoRESUMO
Several 3,5-disubstituted isoxazoles were obtained in good yields by regiospecific 1,3-dipolar cycloaddition reactions between aromatic nitrile oxides, generated in situ from the corresponding hydroxyimidoyl chlorides, with non-symmetrical activated alkynes in the presence of catalytic amounts of copper(I) iodide. Effects of 3,5-disubstituted isoxazoles on nitric oxide and reactive oxygen species generation in Arabidopsis tissues was studied using specific diaminofluoresceine dyes as fluorescence indicators.
