Synthesis And Biological Activity Of 1,4-pentadien-3-one Derivatives Containing Benzotriazinone

The curcumin analog penta-1,4-dien-3-ones are the same as curcumin,which was found to exhibit desirable bioactivities including bactericidal,antiviral,insecticidal,anti-infammatory,anti-oxidative and anticancer properties.the structure of penta-1,4-dien-3-one is more stable than that of curcumin under neutral or alkaline condition.In addition,the last decade studies reported that penta-1,4-dien-3-one can serve as potential alternative templates in the search for novel,highly efcient virucides.Meanwhile,benzotriazin-4?3H?-one was regarded as an important nitrogenous motif that was commonly used in developing for agrochemicals.Considering these above findings,series of penta-1,4-diene-3-one?oxime?ether derivatives bearing benzotriazin-4?3H?-one,which confirmed by ¹H NMR,¹³C NMR and HRMS,were designed and synthesized.My main work and findings are summerized bellow:1.Thirty four penta-1,4-dien-3-one derivatives containing a benzotriazin-4?3H?-one moiety were designed and synthesized in the present work.Using the commercial agent ribivirin and ningnamycin as the control under the same conditions,their antiviral activities against tobacco mosaic virus?TMV?were tested at concentration of 500?g/mL based on the half leaf blight spot method.In terms of their curative activities,the compounds A4,A20,A22 and A28 exhibited visible antiviral activity against TMV,with the inhibitory rates of 49.0,48.6,44.2 and 52.8%,respectively,which are better than ribivirin?35.0%?.In terms of their protective activities,the inhibitory rates of compounds A4,A5,A8,A20,A22,A23,A24 and A28 were52.9?59.2?57.7?60.3?57.3?56.0?57.4 and 61.6%,respectively,which are better than that of ribivirin?50.8%?.Meanwhile,the inhibitory rates of compound A28 in its curative and protective activities was equal to ningnamycin?54.4 and62.4%?.Using the commercial agents thiodiazole copper and bismerthiazol as the control under the same conditions,the antibacterial activities of some title compounds against Xanthomonas axonopodis pv.citri?Xac?and Ralstonia solanacearum?R.solanacearum?and Xanthomonas oryzae pv.Oryzae?Xoo?at concentration of 100and 50?g/mL were evaluated based on the turbidimeter test.Bioassays indicated that some compounds exhibited good antibacterial and antiviral activities.Among them,the inhibition rate of compound A31 against R.solanacearum at 100?g/mL was100%.The inhibition rate of compound A12 against R.solanacearum at 100?g/mL was 88.14%.Compounds A4,A11,A21,A26 and A29 had fine antibacterial activity against Xoo at 100?g/mL,with the inhibition rates of 100%.And Compounds A2,A5,A24,A27,A28,A30 and A31 had good antibacterial activity against Xoo at 100?g/mL,with the inhibition rates better than 80%.The EC₅₀0 values of compound A4against Xac and compound A12 against Rs were respectively 22.45 and 34.77?g/mL,which were better than that of thiodiazole copper?51.35 and 87.26?g/mL,respectively?.Six penta-1,4-dien-3-one oxime ether derivatives containing a benzotriazin-4?3H?-one moiety were designed and synthesized in the present work.Using the commercial agent ribivirin and Ningnamycin as the control under the same conditions,their antiviral activities against TMV were tested at concentration of 500?g/mL based on the half leaf blight spot method.The bioassay indicated that these compounds exhibited moderate antibacterial activity against TMV 500?g/mL,which are inferior to ribivirin and Ningnamycin.Using the commercial agents thiodiazole copper and bismerthiazol as the control under the same conditions,the antibacterial activities of some title compounds against Xac and R.solanacearum and Xoo at concentration of100 and 50?g/mL were evaluated based on the turbidimeter test.Bioassays indicated that these compounds exhibited lower activities against three bacterial.