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 <b>N2</b> and <b>N7</b> 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). <b>N2</b> and <b>N10</b> 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 <b>N2</b> 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 <b>N2</b> was shorter and its binding was closer. Meanwhile, when the heartleaf tobacco was being treated with <b>N2</b>, its increasing rate of malondialdehyde slowed and its content of defense enzymes significantly increased, again reflecting the good activity of <b>N2</b> against TMV.