LAUSR

BACKGROUND Potato virus Y (PVY) was first discovered by Smith in 1931 and has currently been ranked as the fifth in the most significant plant viruses. It can cause severe damage to the plants from the family Solanaceae, which results in billions of dollars' economic loss worldwide every year. In order to discover the new antiviral drugs, a class of multi-functional urazole derivatives bearing a stereogenic C-N axis were synthesized with excellent optical purities for antiviral evaluations against the significant plant virus PVY. RESULTS The absolute configurations of the axially chiral compounds have exhibited obvious distinctions in the antiviral bioactivities, with several of the enantio-enriched axially chiral molecules showed excellent anti-PVY activities. Especially, compound (R)-9f exhibited remarkable curative activities against PVY with the EC50 values of 224.9 μg/mL, which was better than that of the NNM with the EC50 values of 234.0 μg/mL. The EC50 value of the compounds (R)-9f in the protective effects was 462.2 μg/mL, which was comparable to that of NNM (442.0 μg/mL). And then mechanisms of one group of the axially chiral compounds 9f studied by both molecule docking and defensive enzyme activity tests. CONCLUSION Mechanistic studies demonstrated that the axially chiral configurations of the compounds had played significant roles in the molecule PVY-CP interactions and could enhance the activities of the defense enzymes. The current study has provided significant information on the roles that the axial chiralities played in plant protections against plant viruses, which also paved the way towards the development of novel green pesticides bearing axial chiralities with excellent optical purities. This article is protected by copyright. All rights reserved.