Design, Synthesis, and Bioactivity of Chalcone Derivatives Containing Indanone

Abstract

A series of chalcone derivatives containing indanone were designed and synthesized by aldehyde-ketone condensation and etherification. The activity test demonstrated that the majority of the compounds had good therapeutic and protective activities against tobacco mosaic virus (TMV) at a concentration of 500 μg/mL when being tested. Among them, the target compounds N2 and N7 showed good therapeutic activities against TMV with EC50 values of 70.7 and 89.9 μg/mL, respectively, which were better than that of ningnanmycin (158.3 μg/mL). N2 and N10 showed better protective activities against TMV with EC50 values of 60.8 and 120.3 μg/mL, which were superior to that of ningnanmycin (175.6 μg/mL). A hydrogen bond interaction was observed between N2 and ARG-341 with a bond length of 3.08 Å and a hydrogen bond was observed between ningnanmycin and ASP-66 with a bond length of 3.72 Å. In contrast, the hydrogen bond length of compound N2 was shorter and its binding was closer. Meanwhile, when the heartleaf tobacco was being treated with N2, its increasing rate of malondialdehyde slowed and its content of defense enzymes significantly increased, again reflecting the good activity of N2 against TMV.[Figure presented]