Synthesis And Bioactivities Of Novel Chiral 2-Cyanoacrylates Derivatives

2-Cyanoacrylate is a kind of compound with versatile biological activities applied in agrochemistry widely. In our previous work about synthesis of cyanoacrylates including pyridyl and trifluoromethyl moiety, these compounds were found to possess modest anti-TMV activities and antiproliferation activities to PC3 cells for the first time. So a series of new chiral compounds targeted on TMV were designed and synthesized by introducing (R)-or (S)-1-phenylethylamine into cyanoacrylate and hoped to screen compounds with high anti-virus activities.Started from ethyl cyanoacetate, 39 title compounds were synthesized under microwave irradiation, among which 22 were chiral ones. All compounds were confirmed by ¹H NMR, ¹³C NMR, IR and elemental analysis. The crystal structures of compounds Ia and IIa-R were confirmed by X-ray diffraction. From the crystal structure we got that compounds I and II were both of E-isomer. X-ray intensity data of IIa-R listed as followings: the crystal belongs to orthorhombic crystal system, space group is Pca 21, a = 0.9152 (3) ran, b = 1.1221 (4) nm, c = 2.0691 (6) nm, V = 2.1249 (11) nm³, Z= 4, Dx = 1.261 g/cm³,λ = 7.1073 nm, θ = 2.06° 25.01°,μ = 0. 100 mm^-1 and F (000) = 840, the final least-squares cycle gave R = 0.0707, wR = 0.1786, respectively. Δρ_max = 338 e/nm³.To optimize the reaction conditions, the synthesis of I and II were carried out under several conditions. The effects of different solvents, reaction time, and the use of microwave irradiation on the reaction or not were investigated. The conditions more viable obtained: under microwave irradiation of 600W at 50℃ for 30 45 minutes, compounds I were synthesized with high yields (64.0 93.5%); and at 600W, 97℃ reacted for 20 30 min obtained compounds II with yields between 57.6 82.3%. Comparing with the drawbacks of the classical method, the present one offers several advantages including greener, faster reaction rates, fewer byproducts, and higher yields.The title compounds were evaluated for herbicidal, anticancer and anti-TMV activities. And the results of bioassay showed that: compounds designed did not show herbicidal activity but possessed promising activities against TMV, curative effect of compounds 05178, IIf-5 and IIk against TMV in vivo are higher than...