Synthesis And Biological Activity Of Pentadienone And Chalcone Derivatives Containing Triazole Heterocycles

In this paper,a series of triazole heterocycle derivatives containing pentadienone(Y₁-Y₃₃)and chalcone(Z₁-Z₁₆)were synthesized.The structures of the novel compounds were systematically characterized via ¹H NMR,¹³C NMR and HRMS.And conducted a biological activity test.Antibacterial activity of the compounds were tested by turbidity method.Bioassays indicated that some of the compounds showed potential antibacterial activities against Xac,Xoo and Rs.Among them,compounds Y₆,Y₁₆,Y₁₈,Y₂₂,Y₂₃,Y₂₅,Y₃₂,Y₃₃,Z₁₁ and Z₁₅ demonstrated appreciable inhibitory effect against Xac,with half-maximal effective concentration(EC₅₀)values of 9.9,15.9,6.6,9.9,9.2,5.4,7.5,7.8,15.1 and 9.1μg/m L,which were better than commercial agent bismerthiazol（54.9μg/m L）.Compounds Y₁,Y₂₈,Y₃₁ and Z₁₀ demonstrated appreciable inhibitory effects against Xoo with EC₅₀ values of 9.6,10.9,17.5 and 10.8μg/m L,which were better than commercial agent bismerthiazol（69.3μg/m L）.Compounds Y₃ and Y₆also demonstrated appreciable inhibitory effects against Ralstonia solanacearum with EC₅₀values of 14.2 and 14.5μg/m L,which were better than commercial agent bismerthiazol（82.6μg/m L）.Furthermore,we used scanning electron microscopy（SEM）to study the possible sterilization process of the target compound Y₂₅ against Xac.The results indicated the possibility of destroying the bacterial cell membrane structure,resulting in an incomplete bacterial structure,and thus achieving inhibition.The half-leaf method was used to test the antiviral bioassays indicated that some of compounds showed excellent protective,curative activities against tobacco mosaic virus（TMV）.Compounds Y₂₁,Y₂₈and Y₃₁ showed good protective activity against TMV with EC₅₀ value of 108.3,108.9 and 105.4μg/m L,which were better than commercial agent ningnanmycin（214.7μg/m L）;meanwhile,compound Y₂₆demonstrated curative activities against TMV with EC₅₀ valus of 281.9μg/m L respectively,which were superior to that of ningnanmycin（469.9μg/m L）.The molecular docking study of the target compound Y₁₈ and TMV-CP showed that the compound Y₁₈ interacted with TMV-CP in part.Therefore,the mechanism of action of compound Y₁₈ can be further studied.