Abstract
A series of novel phosphorylated penta-1,4-dien-3-one derivatives were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and high-resolution mass spectrometry (HRMS). Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compound 3g exhibited substantial antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), with a 50% effective concentration (EC50) value of 8.6 μg/mL, which was significantly superior to bismerthiazol (BT) (58.8 µg/mL) and thiodiazole-copper (TC) (78.7 μg/mL). In addition, compound 3h showed remarkable protective activity against tobacco mosaic virus (TMV), with an EC50 value of 104.2 μg/mL, which was superior to that of ningnanmycin (386.2 μg/mL). Furthermore, the microscale thermophoresis and molecular docking experiments on the interaction of compounds 3h and 3j with TMV coat protein (TMV CP) were also investigated. Compounds 3h and 3j bound to TMV CP with dissociation constants of 0.028 and 0.23 μmol/L, which were better than that of ningnanmycin (0.52 μmol/L). These results suggest that novel phosphorylated penta-1,4-dien-3-one derivatives may be considered as an activator for antibacterial and antiviral agents.
Highlights
IntroductionBacterial diseases, such as rice bacterial leaf blight and citrus canker, caused by the pathogens
Bacterial diseases, such as rice bacterial leaf blight and citrus canker, caused by the pathogensXanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) [1,2,3,4], strongly restrain the agricultural output worldwide and are difficult to control in agriculture
Because the phosphorus–carbon bond of efficient based agrochemicals, we introduced ashow penta-1,4-diene-3-one group into synthesized phosphate derivatives, Pesticides on natural products more advantages chemicals, e.g., phosphonate derivatives is not susceptible to enzymatic degradation,than they possess improved cell which might generate novel phosphate derivatives with potent biological activities
Summary
Bacterial diseases, such as rice bacterial leaf blight and citrus canker, caused by the pathogens. In a previous study from our group, we synthesized a series of penta-1,4-dien-3-one derivatives, most of which exhibited excellent antiviral activities [13,17,18]. Because the phosphorus–carbon bond of efficient based agrochemicals, we introduced ashow penta-1,4-diene-3-one group into synthesized phosphate derivatives, Pesticides on natural products more advantages chemicals, e.g., phosphonate derivatives is not susceptible to enzymatic degradation,than they possess improved cell which might generate novel phosphate derivatives with potent biological activities. According to previous reports [15,29], 2-hydroxybenzaldehyde and acetone were used phosphorylated penta-1,4-dien-3-one derivatives were designed, synthesized, and evaluated for their Phosphonates their immediate derivatives possess a at wide range of biological activities [19–.
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