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Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2022-05-31 , DOI: 10.1016/j.arabjc.2022.104019
Tingting Liu , Feng Peng , Yunying Zhu , Xiao Cao , Qifan Wang , Fang Liu , Liwei Liu , Wei Xue

Plant bacteria and viruses have a huge negative impact on food crops in the world. Therefore, it is important to create new and efficient green pesticides. In this paper, a series of myricetin derivatives containing quinazolinone sulfide were introduced. Good antibacterial and antiviral activities of the drug molecules 2-((3-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)propyl)thio)-6-fluoro-3-phenylquinazolin-4(3H)-one (T5) and 2-((4-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy)butyl)thio)-6-methyl-3-phenylquinazolin-4(3H)-one (T15) respectively were found by biological activity screening. The value of dissociation constant (Kd) of compound T15 to TMV CP was 0.024 ± 0.006 μM, determined by Microscale thermophoresis (MST), which was far less than the value of 8.491 ± 2.027 μM of commercial drug ningnanmycin (NNM). The interaction between compound T15 and TMV CP was further verified by molecular docking. Compound T15 formed strong hydrogen bonds with residues SER:49 and SER:15 (1.92 Å, 2.20 Å, respectively), which were superior to the traditional hydrogen bonds formed by NNM with residue SER:215 (3.64 Å). In addition, the effects of compound T15 on the contents of chlorophyll and peroxidase (POD) in tobacco were studied, and the results indicated that compound T15 could enhance the disease resistance of tobacco plants to a certain extent.



中文翻译:

含硫醚喹唑啉酮杨梅素衍生物的设计、合成、生物活性评价及作用机制

植物细菌和病毒对世界粮食作物产生巨大的负面影响。因此,研发新型高效绿色农药显得尤为重要。本文介绍了一系列含有喹唑啉酮硫化物的杨梅素衍生物。药物分子2-((3-((5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4 H -chromen-3-yl)oxy)具有良好的抗菌和抗病毒活性丙基)硫代)-6-fluoro-3-phenylquinazolin-4(3 H )-one ( T5)和 2-((4-((5,7-dimethoxy-4-oxo-2-(3,4,5)通过生物活性筛选分别发现-三甲氧基苯基)-4 H-色烯-3-基)氧基)丁基)硫代)-6-甲基-3-苯基喹唑啉-4(3 H)-一(T15) 。解离常数的值 (微量热泳(MST)测定,化合物T15对TMV CP的K d为0.024±0.006μM,远低于商品药宁南霉素(NNM)的8.491±2.027μM。通过分子对接进一步验证了化合物T15与TMV CP之间的相互作用。化合物T15与残基 SER:49 和 SER:15(分别为 1.92 Å,2.20 Å)形成强氢键,优于 NNM 与残基 SER:215(3.64 Å)形成的传统氢键。此外,研究了复方T15对烟草中叶绿素和过氧化物酶(POD)含量的影响,结果表明复方T15能在一定程度上增强烟草植株的抗病性。

更新日期:2022-05-31
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