Containing 3,4,5 - Trimethoxyphenyl And Bromo Phenyl The Aminophosphonates Compounds Synthesis And Biological Activity Study

α-Aminophosphonates, analogues of natural amino acids, are an important class of active compounds. They exhibit a wide range of biological activities such as anti-plant virus, plant growth regulators, herbicidal, antifungal, antitumor activities and so on. In recent years, they also have been found to display anti-tobacco mosaic virus activity. Therefore, the synthesis and biological activities ofα-Aminophosphonates have been a focus of considerable attention in synthetic organic chemistry as well as in medicinal chemistry.In order to find new compounds with high antiviral activity against the tobacco mosaic virus (TMV), 3, 4, 5-trimethoxybenzyl and bromophenyl gruops were introduced intoα-aminophosphonates by combining the active groups in the design of compounds in the thesis. The same series of eight newα-aminophosphonates containing 3, 4, 5-trimethoxybenzyl and bromophenyl groups were synthesized by the Kabachnik-Fields reaction of 3, 4, 5-trimethoxybenzaldehyde (TMB) with m-or p-bromoaniline and a dialkyl phoshphite under solvent-free conditions using no catalyst and BF₃·Et₂O catalyst respectively. 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. At the same time, the spectroscopic properties, the synthetic method and the reaction conditions were systematically analyzed and discussed in the thesis. Compound Ig was also characterized by X- ray crystallography. The crystal belongs to the monocline system with space group P2 (1)/c, a= 12.7429(14) nm, b = 14.1740(16) nm, c = 14.2643(15) nm,α= 90.00°,β= 107.360(6)°,γ= 90.00°, V=2459.0(5)nm³, Z=4,Dc= 1.395 mg/m³,μ= 1.77 mm^-1, F (000) = 1072.0. There also exists an intramolecular hydrogen bond N(1)-H(1)…O(4) in the molecule of compound Ig. A half-leaf mehtod was used to determine the in vivo curative efficacy of the eight title products against (TMV). The results show that these compounds have some antiviral activity against TMV. Compound Ih (R¹ = n-Pr, R² = 3-Br)could cure TMV up to 54.5% at 500μg/mL and compound Ih has equivalent curative activity to Ningnanmycin's (at the same testing conditions, the inhibition of Ningnanmycin which served as reference antiviral agent is 57.5%).