Synthesis and biological activity of hydroxycinnamoyl containing antiviral drugs (original) (raw)

Seven N-hydroxycinnamoyl amides were synthesized by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide/1-hydroxybenzotriazole (EDC/HOBt) coupling of the corresponding substituted cinnamic acids (p-coumaric-, ferulic-, sinapic-and caffeic acids) with influenza antivirals (amantadine, rimantadine and oseltamivir). The DPPH (1,1-diphenyl-2-picrylhydrazyl) scavenging abilities and the inhibitory effect on mushroom tyrosinase activity (using L-tyrosine as the substrate) were investigated in vitro. Amongst the synthesized com- , containing a catechol moiety, exhibited the most potent DPPH radical-scavenging activity. Amide (1) also displayed tyrosinase inhibitory effect toward L-tyrosine as the substrate (≈50 %). The synthesized compounds were also investigated for their in vitro inhibitory activity against the replication of influenza virus A (H3N2).