Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base

Chen Ying; Li Pu; Su Shijun; Chen Mei; He Jun; Liu Liwei; He Ming; Wang Hua; Xue Wei

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Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base

机译：含有1,2,4-三唑席夫基地的霉菌素衍生物的合成及抗菌和抗病毒活性

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A series of novel myricetin derivatives containing a 1,2,4-triazole Schiff base were designed and synthesized. Their structures were systematically characterized using H-1 NMR, C-13 NMR, and HRMS. During antibacterial bioassays, 6f, 6i, and 6q demonstrated a good inhibitory effect against Xanthomonas axonopodis pv. citri (Xac), with half-maximal effective concentration (EC50) values of 10.0, 9.4, and 8.8 mu g mL(-1), respectively, which were better than those of bismerthiazol (54.9 mu g mL(-1)) and thiodiazole copper (61.1 mu g mL(-1)). Note that 6w demonstrated a good inhibitory effect against Ralstonia solanacearum (Rs) with and EC50 value of 15.5 mu g mL(-1), which was better than those of bismerthiazol (55.2 mu g mL(-1)) and thiodiazole copper (127.9 mu g mL(-1)). Similarly, 6a, 6d, and 6e demonstrated a good inhibitory effect against Xanthomonas oryzae pv. oryzae (Xoo) with EC50 values of 47.1, 61.2, and 61.0 mu g mL(-1), respectively, which were better than those of bismerthiazol (148.2 mu g mL(-1)) and thiodiazole copper (175.5 mu g mL(-1)). Furthermore, we used scanning electron microscopy (SEM) to study the possible sterilization process of the target compound 6q against Xac. The results indicated the possibility of destroying the bacterial cell membrane structure, resulting in an incomplete bacterial structure, and thus achieving inhibition. Furthermore, antiviral bioassays revealed that most compounds exhibited excellent antiviral activity against tobacco mosaic virus (TMV) at a concentration of 500 mu g mL(-1). The results of the molecular docking studies for 6g with TMV-CP (PDB code: ; 1EI7) showed that compound 6g had partially interacted with TMV-CP. Therefore, mechanistic studies of the action of compound 6g could be further studied based on that.

机译：设计并合成了一系列含有1,2,4-三唑席夫底座的新型霉菌素衍生物。系统地使用H-1 NMR，C-13 NMR和HRMS系统地进行了它们的结构。在抗菌生物测定期间，6f，6i和6q展示了对Xanthomonas Axonopodis PV的良好抑制作用。 Citri（XAC）分别具有10.0,9.4和8.8μg（-1）的半最大有效浓度（EC 50）值，比铋（54.9μg（-1））更好硫齐唑铜（61.1μgml（-1））。注意，6W对Ralstonia solanacearum（Rs）的良好抑制效果和EC50值为15.5μgmm（-1），其优于铋（55.2μgml（-1））和硫代唑铜（127.9 mu g ml（-1））。类似地，6A，6D和6E对Xanthomonas Oryzae PV进行了良好的抑制作用。 ORYZAE（XOO）分别具有47.1,61.2和61.0μmGml（-1）的EC 50值，其优于二氧化硫吡喃（-148.2μg（-1））和硫代噻唑铜（175.5μgml（ -1））。此外，我们使用扫描电子显微镜（SEM）来研究靶化合物6q的可能灭菌过程对XAC。结果表明破坏细菌细胞膜结构的可能性，导致细菌结构不完全，从而实现抑制。此外，抗病毒生物测定表明，大多数化合物以500μgmm（-1）的浓度为烟草薄皮病毒（TMV）的优异的抗病毒活性。具有TMV-CP的6G的分子对接研究的结果（PDB代码：1EI7）显示化合物6g与TMV-CP部分相互作用。因此，可以基于该方法进一步研究化合物6g作用的机械研究。

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《RSC Advances》 |2019年第40期|共8页
作者
Chen Ying; Li Pu; Su Shijun; Chen Mei; He Jun; Liu Liwei; He Ming; Wang Hua; Xue Wei;
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作者单位

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

Hubei Acad Agr Sci Inst Plant Protect &

Soil Sci Wuhan 430064 Hubei Peoples R China;

Guizhou Univ State Key Lab Breeding Base Green Pesticide &

Agr Key Lab Green Pesticide &

Agr Bioengn Minist Educ Ctr Res &

Dev Fine Chem Guiyang 550025 Guizhou Peoples R China;

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1. Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base [J] . Chen Ying, Li Pu, Su Shijun, RSC Advances . 2019,第40期

机译：含有1,2,4-三唑席夫基地的霉菌素衍生物的合成及抗菌和抗病毒活性
2. Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base [J] . Ying Chen, Pu Li, Shijun Su, RSC Advances . 2019,第40期

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3. Synthesis, Antibacterial, Antiurease, and Antioxidant Activities of Some New 1,2,4-Triazole Schiff Base and Amine Derivatives [J] . Sokmen Bahar Bilgin, Gumrukcuoglu Nurhan, Ugras Serpil, Applied biochemistry and biotechnology, Part A. enzyme engineering and biotechnology . 2015,第2期

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Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base

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