Synthesis, antiviral activity, and 3D-QSAR study of novel chalcone derivatives containing malonate and pyridine moieties

Abstract

Several novel chalcone derivatives containing malonate and pyridine moieties were synthesized, and their structures were confirmed by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, 19F nuclear magnetic resonance, infrared, and elemental analyses. Antiviral bioassays revealed that most of the compounds exhibited good antiviral activity against cucumber mosaic virus (CMV) at 500 μg/mL. In particular, compounds 5l and 5n showed significant curative activities against CMV in vivo with 50% effective concentration (EC50) values of 186.2 and 211.5 μg/mL, respectively; these values are even better than that of ningnanmycin (330.5 μg/mL). A 3D quantitative structure–activity relationship study was carried out using the comparative molecular field analysis technique based on curative activities against CMV. Results revealed good predictive ability with cross-validated q2 and non-cross-validated r2 values of 0.517 and 0.990, respectively. Keywords: Chalcone derivatives, Malonate moiety, Pyridine moiety, Antiviral activity, Cucumber mosaic virus, 3D-QSAR