Design, Synthesis And Biological Activity Of Quinazolinone-containing Pentadienone And Chalcone Derivative

In this paper,1,4-pentadiene-3-one derivatives were synthesized from mono-hydroxy substituted benzaldehyde and acetone,and reacted with aromatic formaldehyde.Chalcones were synthesized by replacing formaldehyde with p-hydroxyacetophenone and aromatic compounds.Finally,quinazolinone will be introduced into 1,4-pentadiene-3-one and chalcone;Quinazolinone-containing 1,4-pentadiene-3-one derivative（W1-W20）and chalcone containing chalcone derivative（Z1-Z25）were synthesized and characterized NMR and HRMS.Preliminary activity tests of antibacterial,antifungal and antiviral activities were carried out by turbidimetry method,mycelium growth rate method and half-leaf blip method.Based on the test results,the mechanism of some target compounds was preliminarily studied.Relevant work is summarized as follows:1.The results of bacteriostatic activity test showed that compounds W13 and W16had good antibacterial activity against Xac,with EC₅₀ values of 43.4 and 61.1μg/m L,respectively,which were better than the control agents bismerthiazol（62.3μg/m L）and thiodiazole copper（96.7μg/m L）.The EC₅₀values of compounds Z13,Z20 and Z25against Xac were 79.9,60.6 and 23.5μg/m L,respectively,which were better than that of bismerthiazol（68.1μg/m L）and thiodiazole copper（97.2μg/m L）.The EC₅₀ value of Z7 was 63.2μg/m L,which was better than that of bismerthiazol（78.5μg/m L）and thiodiazole copper（93.8μg/m L）.The EC₅₀ values of compounds Z17 and Z25 against Xoo were 60.9 and 19.5μg/m L,respectively,which were better than that of bismerthiazol（77.71μg/m L）and thiodiazole copper（95.9μg/m L）.Scanning electron microscopy（SEM）showed that with the increase of compound Z25 concentration,the morphology of Xoo bacteria changed from full to wrinkled to broken,so it was concluded that compound Z25 could inhibit the normal growth of Xoo bacteria to a certain extent.2.The results showed that compound W12 showed better inhibitory activity against Sclerotinia sclerotiorum,with EC₅₀ value of 0.70μg/m L,better than azoxystrobin（8.51μg/m L）and EC₅₀ value of 3.84μg/m L against Phomopsis sp.Better than control drug azoxystrobin（17.25μg/m L）.In vitro experiments of rape and kiwi,compound W12showed good inhibitory activity.In terms of protective activity,compound W12 showed better control effect of 91.7%on sclerotinia rapeseed leaves at 100μg/m L,than the control drug pyrimethanil 90.2%.At 200μg/m L,the control effect of compound W12on Phomopsis sp on postharvest kiwi was 96.2%,better than that of control drug azoxystrobin 94.6%.Scanning electron microscopy（SEM）showed that W12 deformed the mycelium surface of sclerotinia rape,resulting in serious curling and folding,which inhibited the normal growth of sclerotinia rape.3.The antiviral activity test results showed that the EC₅₀ values of Z5,Z12 and Z20were 184.3,94.3 and 179.2μg/m L,respectively,which were better than Ningnanmycin216.1μg/m L.The EC₅₀ values of Z5,Z7 and Z12 were 180.1,159.4 and 98.8μg/m L,respectively,which were better than Ningnanmycin 189.6μg/m L.The results of microsurge test showed that the binding K_d value of Z12 to tobacco Mosaic virus coat protein（TMV-CP）was 0.033±0.014μmol/L,which was better than the K_d value of Ningnamycin（0.106±0.024μmol/L）,indicating that the affinity of Z12 to TMV-CP was better than Ningnamycin.Transmission electron microscopy（TEM）showed that Z12 caused TMV virus particles to fracture and form rod-like structures of different lengths.