5-Substituted benzylidene 3-acylthiotetronic acids are antifungal.A series of 3-acylthiotetronic acid derivatives with varying substitutions at the 5-position were designed,synthesized,and characterized,based on the b...5-Substituted benzylidene 3-acylthiotetronic acids are antifungal.A series of 3-acylthiotetronic acid derivatives with varying substitutions at the 5-position were designed,synthesized,and characterized,based on the binding pose of 3-acyl thiolactone with the protein C171Q KasA.Fungicidal activities of these compounds were screened against Valsa Mali,Curvularia lunata,Fusarium graminearum,and Fusarium oxysporum f.sp.lycopersici.Most target compounds exhibited excellent fungicidal activities against target fungi at the concentration of 50μg·mL-1.Compounds 11c and 11i displayed the highest activity with a broad spectrum.The median effective concentration(EC50)values of 11c and 11i were 1.9–10.7 and 3.1–7.8μg·mL-1,respectively,against the tested fungi,while the EC50 values of the fungicides azoxystrobin,carbendazim,and fluopyram were respectively 0.30,4.22,and>50μg·mL-1 against V.Mali;6.7,41.7,and 0.18μg·mL-1 against C.lunata;22.4,0.42,and 0.43μg·mL-1 against F.graminearum;and 4.3,0.12,and>50μg·mL-1 against F.oxysporum f.sp.lycopersici.The structures and activities of the target compounds against C.lunata were analyzed to obtain a statistically significant comparative molecular field analysis(CoMFA)model with high prediction abilities(q2=0.9816,r2=0.8060),and its reliability was verified.The different substituents on the benzylidene at the 5-position had significant effects on the activity,while the introduction of a halogen atom at the benzene ring of benzylidene was able to improve the activity against the tested fungi.展开更多
基金This work was financially supported in part by the National Natural Science Foundation of China(31901906)the Opening Project of Shanghai Key Laboratory of Chemical Biology,the Natural Science Foundation of Anhui Province,China(1808085QC71)+1 种基金the Natural Science Foundation of Anhui Education Department(KJ2016A834)the US Department of Agriculture(USDA:HAW5032-R).
文摘5-Substituted benzylidene 3-acylthiotetronic acids are antifungal.A series of 3-acylthiotetronic acid derivatives with varying substitutions at the 5-position were designed,synthesized,and characterized,based on the binding pose of 3-acyl thiolactone with the protein C171Q KasA.Fungicidal activities of these compounds were screened against Valsa Mali,Curvularia lunata,Fusarium graminearum,and Fusarium oxysporum f.sp.lycopersici.Most target compounds exhibited excellent fungicidal activities against target fungi at the concentration of 50μg·mL-1.Compounds 11c and 11i displayed the highest activity with a broad spectrum.The median effective concentration(EC50)values of 11c and 11i were 1.9–10.7 and 3.1–7.8μg·mL-1,respectively,against the tested fungi,while the EC50 values of the fungicides azoxystrobin,carbendazim,and fluopyram were respectively 0.30,4.22,and>50μg·mL-1 against V.Mali;6.7,41.7,and 0.18μg·mL-1 against C.lunata;22.4,0.42,and 0.43μg·mL-1 against F.graminearum;and 4.3,0.12,and>50μg·mL-1 against F.oxysporum f.sp.lycopersici.The structures and activities of the target compounds against C.lunata were analyzed to obtain a statistically significant comparative molecular field analysis(CoMFA)model with high prediction abilities(q2=0.9816,r2=0.8060),and its reliability was verified.The different substituents on the benzylidene at the 5-position had significant effects on the activity,while the introduction of a halogen atom at the benzene ring of benzylidene was able to improve the activity against the tested fungi.