Design, Synthesis and Anti‐PVY Activity of Planar Chiral Thiourea Derivatives Incorporated with [2.2]Paracyclophane

AbstractBACKGROUNDPotato virus Y (PVY) stands as a prominent representative in the realm of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover the new antiviral agents, a class of planar chiral thiourea molecules through the key step of N‐heterocyclic carbene‐catalyzed nitrile formation reaction were synthesized with excellent optical purities for antiviral evaluations against plant virus PVY.RESULTSThe absolute configurations of the planar chiral compounds have exhibited obvious distinctions in the anti‐PVY activities. Notability, compound (S)‐4u exhibited remarkable curative activities against PVY, with the half maximal effective concentration values of 349.3 μg/mL, which was better than that of the ningnanmycin with the EC50 values of 400.8 μg/mL. Additionally, The EC50 value for the protective effects of (S)‐4u was 146.2 μg/mL, which was superior to that of NNM (276.4 μg/mL). Furthermore, the mechanism of action of enantiomers of planar chiral compound 4u was investigated through molecular docking, defensive enzyme activity tests and chlorophyll content tests.CONCLUSIONBiological mechanism studies have demonstrated that the configuration of planar chiral target compounds plays a crucial role in the molecular interaction with PVY‐CP, enhancing the activity of defense enzymes and affecting chlorophyll content. The current study has provided significant insights into the roles played by planar chiralities in plant protection against viruses. This paves the way for the development of novel green pesticides bearing planar chiralities with excellent optical purities.This article is protected by copyright. All rights reserved.