Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents.

ABSTRACT

A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 µg/mL and 206.3, 186.2 µg/mL, respectively, better than those of ribavirin (848.0, 808.1 µg/mL and 858.2, 766.5 µg/mL, respectively), dufulin (462.6, 454.8 µg/mL and 471.2, 465.4 µg/mL, respectively), and ningnanmycin (440.5, 425.3 µg/mL and 426.1, 405.3 µg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)dithioacetal as new antiviral agents.