Synthesis And Biological Activity Of Chalcone Derivatives Containing 1,1-dichloropropene

In this paper, chalcone derivatives, which have widely biological activities, are introduced into 1,1-dichloropropene compounds, we aim to introduce nitromethane fragments to the parent chalcone skeleton by Michael reaction, 26 novel 1,1-dichloropropene derivatives containing chalcone moiety were designed and synthesized, the physical characteristics were confirmed by 1H NMR, 13 C NMR, IR and elemental analysis. Then their antiviral activities were evaluated by half leaf blight spot method and results showed that some of the title compounds exhibited excellent antiviral activities against tobacco mosaic virus(TMV). Finally, the interactions between target compounds and TMV CP were also explored. The conclusions are shown as follows:1. Starting from chalcone as the guide compound, we aim to introduce nitromethane fragments to the parent chalcone skeleton by Michael reaction, and introduce into pyridalyl by etherification reaction, 26 novel 1,1-dichloropropene derivatives containing chalcone moiety were designed and synthesized, the physical characteristics were confirmed.2. The antiviral activity against TMV of the title compounds 7a–7z was determined using the half-leaf method with commercial product Ningnanmycin as control, the bioassay results indicated that most of the target compounds exhibited good activity against tobacco mosaic virus(TMV) at the concentration of 500 mg/L. Especially, compound 7s showed the best protection activity against TMV at 500 mg/L, with the inhibition rate of 76.61%, which was similar to that of Ningnanmycin(94.13%). and compounds 7g, 7h, 7m, 7n, 7w, and 7z showed excellent inactivation activity against TMV at 500 mg/L, with the inhibition rates of 93.15%, 94.88%, 93.51%, 92.96%, 94.02% and 93.15%, respectively, which were similar to that of Ningnanmycin(94.13%). Then, the EC50 values of inactivation activities against TMV of the target compounds were evaluated. Especially, compound 7h exhibited the best inactivation activity against TMV, with the EC50 value of 45.6 ?g/mL, which was similar to that of Ningnanmycin(46.9 ?g/mL).3. In order to further study the interactions between target compounds and TMV CP, the fluorescence spectroscopy and microscale thermophoresis(MST) analysis method were used, the result showed that compound 7h bound to the tobacco mosaic virus coat protein(TMV CP) with micromole affinity.