Synthesis and antiviral activities of cyanoacrylate derivatives containing an α-aminophosphonate moiety

Article abstract of DOI:10.1021/jf800405m

Target compounds 8 were obtained by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylate or cyarylamide (7a-7e) and α- aminobenzylphosphonate (5a-5e) under reflux condition using ethanol as solvent. Their structures were clearly verified by spectroscopic data (IR and ¹H, ¹³C, and ³¹P NMR) and elemental analysis. These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 8d and 8e had the same inactivation effect against tobacco mosaic virus (EC₅₀ = 55.5 and 55.3 μg/mL) as the commercial product ningnanmycin (EC₅₀ = 50.9 μg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of cyanoacrylate derivatives containing an α-aminophosphonate moiety.