Hu Die, Zhang Nian, Zhou Qing, Zhou Yuanxiang, Gong Chenyu, Zhang Yuanquan, Xue Wei
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China.
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China.
Fitoterapia. 2023 Apr;166:105458. doi: 10.1016/j.fitote.2023.105458. Epub 2023 Feb 14.
A series of novel chalcone derivatives containing pyrazole oxime ethers were designed and synthesized. The structures of all the target compounds were determined by NMR and HRMS. The structure of H5 was further confirmed via single-crystal X-ray diffraction analysis. The results of biological activity test showed that some of the target compounds exhibited significant antiviral and antibacterial activities. The test results of EC value against tobacco mosaic virus showed that H9 had the best curative and protective effect, and the EC value of curative activity of H9 was 166.9 μg/mL, which was superior to ningnanmycin (NNM) 280.4 μg/mL, the EC value of protective activity of H9 was 126.5 μg/mL, which was superior to ningnanmycin 227.7 μg/mL. Microscale thermophoresis (MST) experiments demonstrated that H9 (K = 0.0096 ± 0.0045 μmol/L) exhibited a strong binding ability with tobacco mosaic virus capsid protein (TMV-CP), which was far superior to ningnanmycin (K = 1.2987 ± 0.4577 μmol/L). In addition, molecular docking results showed that the affinity of H9 to TMV protein was significantly higher than ningnanmycin. The results of against bacterial activity showed that H17 has a good inhibiting effect against Xanthomonas oryzae pv. oryzae (Xoo), the EC value of H17 was 33.0 μg/mL, which was superior to the commercial drugs thiodiazole copper (68.1 μg/mL) and bismerthiazol (81.6 μg/mL), and the antibacterial activity of H17 was verified by scanning electron microscopy (SEM).
设计并合成了一系列含吡唑肟醚的新型查尔酮衍生物。所有目标化合物的结构均通过核磁共振（NMR）和高分辨质谱（HRMS）确定。通过单晶X射线衍射分析进一步确证了H5的结构。生物活性测试结果表明，部分目标化合物表现出显著的抗病毒和抗菌活性。抗烟草花叶病毒的毒力（EC）值测试结果显示，H9具有最佳的治疗和保护效果，其治疗活性的EC值为166.9 μg/mL，优于宁南霉素（280.4 μg/mL）；其保护活性的EC值为126.5 μg/mL，优于宁南霉素（227.7 μg/mL）。微量热泳动（MST）实验表明，H9（K = 0.0096 ± 0.0045 μmol/L）与烟草花叶病毒衣壳蛋白（TMV-CP）具有很强的结合能力，远优于宁南霉素（K = 1.2987 ± 0.4577 μmol/L）。此外，分子对接结果表明，H9与TMV蛋白的亲和力显著高于宁南霉素。抗菌活性测试结果显示，H17对水稻白叶枯病菌（Xoo）具有良好的抑制作用，其EC值为33.0 μg/mL，优于市售药剂噻菌铜（68.1 μg/mL）和叶枯唑（81.6 μg/mL），通过扫描电子显微镜（SEM）验证了H17的抗菌活性。
