The Synthesis Of New ¦Á-amino Phosphonates And Their Amide Derivatives And Biological Activity Study

α-Aminophosphonate is a kind of compounds with high biological activities. A series of fluorinated and heterocyclicα-aminophosphonates were synthesized, and their anti-TMV activities were evaluated. In 2002, Bing DuXing, which showed a remarkable activity against mosaic disease of tobacco, was screened out as a kind of anti-TMV medicament.In order to find new a-aminophosphonates and their derivatives with high activity, 3,4,5-trimethoxybenzaldhyde (TMB) was synthesized via a four step synthetic sequence involving etherification, esterification, hydrazidation and oxidation using galic acid as a lead compound. Subsequently, four of newα-aminophosphonates which possessed 3,4,5-trimethoxy- benzyl and trifluoromethyl were firstly synthesized through introducing trifluoromethyl and phosphonate to TMB. The reaction was carried out without solvent in one-pot synthesis. Meantime, active a-aminophosphonates containing amino was successfully obtained via a four step synthetic sequence involving ammoniation, esterification, sulfonation and aminolysis using substituted-benzaldhyde as a reactant. Active amide was introduced to their structures in the catalysis of DCC by one step, and then nineteen of novelα-aminophosphonate derivatives containing phosphonate and amide groups were firstly synthesized. All compounds were confirmed by elemental analysis, infrared spectrum, ¹H NMR, ¹³C NMR and ³¹P NMR. The results of bioassay showed that the two type compounds exhibited certain anti-TMV activity in vivo treatment, especially, III_6f exhibited equivalent curative activity to Ningnanmycin (the efficient rate was 53.63% for III_6f and 55.45% for ningnanmycin at a concentration of 500μg/mL).From the viewpoint of green synthesis and environment-friendly, the green synthetic method of O,O'-dialkyl-α-(4-trifluoromethylanilino)-substitutented benzylphosphonate was compared under different conditions firstly, such as microwave irradiation, ionic liquid, solvent and catalyst free. The optimal synthetic method was screened out and summarized as follows: the ratio of raw materials was 1:1:1, and then the mixture reacted at 100℃without solvent and catalyst, which was economic, convenient, high yields and environment-friendly.