RESUMO
New alpha-aminophosphonates were synthesized by the Kabachnik-Fields reaction of 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkyl phosphite under solvent-free conditions. TMB was prepared from gallic acid via a four step synthetic sequence involving etherification, esterification, hydrazidation and potassium ferricyanide oxidation. The structures of all synthesized compounds were confirmed by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectral data. Compound 7g was also characterized by X-ray crystallography. A half-leaf method was used to determine the in vivo curative efficacy of the eight title products against tobacco mosaic virus (TMV). It was found that compounds 7g and 7h possess good in vivo curative effects against TMV.
Assuntos
Antivirais/síntese química , Nicotiana/efeitos dos fármacos , Organofosfonatos/síntese química , Vírus do Mosaico do Tabaco/efeitos dos fármacos , Antivirais/farmacologia , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Organofosfonatos/química , Organofosfonatos/farmacologia , Folhas de Planta/química , SolventesRESUMO
A simple, efficient, and general method has been developed for the synthesis of various 3-alkylquinazolin-4-one derivatives from quinazolin-4-one treated with alkyl bromides under phase transfer catalysis condition. The structures of the compounds were characterized by elemental analysis, IR, (1)H-NMR and (13)C-NMR spectra. Title compound 6-bromo-3-propylquinazolin-4-one (3h) was found to possess good antifungal activity.
Assuntos
Antifúngicos/síntese química , Antifúngicos/farmacologia , Quinazolinonas/síntese química , Quinazolinonas/farmacologia , Fusarium/efeitos dos fármacos , Gibberella/efeitos dos fármacosRESUMO
A simple, efficient, and general method has been developed for the synthesis of various alpha-aminophosphonate derivatives 4a-4l by treatment of substituted benzaldehydes and aniline with bis(2-methoxyethyl)- or bis(2-ethoxyethyl) phosphite under microwave irradiation without solvents and catalysts. The products were characterized by elemental analysis, IR, 1H-NMR, 13C- and 31P-NMR spectra. The X-ray crystallographic data of the representative compound 4l was determined. The new alpha-aminophosphonate derivatives were found to possess moderate to good antiviral activity.
