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Synthesis and biological evaluation of 1,4-pentadien-3-one derivatives containing 1,2,4-triazole

文献类型： 外文期刊

作者： Chen, Mei 1 ; Wang, Yihui 1 ; Su, Shijun 1 ; Chen, Ying 1 ; Peng, Feng 1 ; Zhou, Qing 1 ; Liu, Tingting 1 ; Luo, Hui 1 ; Wan 1 ;

作者机构： 1.Guizhou Univ, Ctr Res & Dev Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Guiyang 550025, Peoples R China

2.Hubei Acad Agr Sci, Inst Plant Protect & Soil Sci, Wuhan 430064, Peoples R China

关键词： 1,4-Pentadien-3-one; 1,2,4-Triazole; Antibacterial activity; Antiviral activity; Action mechanism; Synthesis

期刊名称：JOURNAL OF SAUDI CHEMICAL SOCIETY （ 影响因子：3.932； 五年影响因子：4.104 ）

ISSN： 1319-6103

年卷期： 2020 年 24 卷 10 期

页码：

收录情况： SCI

摘要： A series of new 1,4-pentadien-3-one derivatives containing 1,2,4-triazole moiety were synthesized. The structures of the synthesized compounds were charactered via H-1 NMR, C-13 NMR and HRMS. Antibacterial bioassays indicated that some of compounds showed potential antibacterial activities against Ralstonia solanacearum (Rs), Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac). Compounds F-8 and F-17 showed good in vitro antibacterial activities against Rs, with the EC50 values of 18.6 and 18.6 mu g/mL, respectively, which were better than commercial agent bismerthiazol (55.2 mu g/mL). Furthermore, compounds F-12 and F-15 showed good in vitro antibacterial activities against Xoo, with the EC50 values of 10.9 and 17.5 mu g/mL, which were better than commercial agent bismerthiazol (69.3 mu g/mL). Moreover, compounds F-2, F-9, F-16 and F-17 showed good in vitro antibacterial activities against Xac, with the EC50 values of 6.6, 5.4, 7.5 and 7.8 mu g/mL, respectively, which were better than commercial agent bismerthiazol (54.9 mu g/mL). The effect of compound F-9 on Xac bacterial cell membrane rupture was observed by scanning electron microscopy (SEM). In addition, antiviral bioassays indicated that some of compounds showed excellent protection activities against tobacco mosaic virus (TMV). Compounds F-5 and F-15 showed good protecting activity against TMV, with the EC50 values of 108.3 and 105.4 mu g/mL, respectively, which were better than commercial agent ningnanmycin (214.7 mu g/mL). Microscale thermophoresis (MST) also showed that the binding of compound F-2 to TMV coat protein (TMV-CP) yielded a Kd value of 1.260 +/- 0.654 mu mol/L, which was very close to ningnanmycin (1.058 +/- 0.286 mu mol/L). Similarly, the molecular docking studies for F-2 and F-5 with TMV-CP (PDB code: 1E17, ID: 4QGH) indicated that compounds F-2 and F-5 had partially interacted with TMV-CP. (C) 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.

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