Synthesis, Antibacterial Activity, and Mechanisms of Novel 6-Sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole Derivatives
Synthesis, Antibacterial Activity, and Mechanisms of Novel 6-Sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole Derivatives
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DOI：
10.1021/acs.jafc.1c01204
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发表时间：
2021-04-19
影响因子：
6.1
通讯作者：
Song, Baoan
中科院分区：
文献类型：
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作者：
Wu, Sikai;Shi, Jing;Song, Baoan
设计并合成了一系列新型6-磺酰基-1,2,4-三唑并[3,4-b][1,3,4]噻二唑衍生物。建立CoMFA模型，根据化合物的EC50值分析定量构效关系。利用该模型设计并合成了具有较高活性的化合物32和33。化合物 33 对米黄单胞菌 pv. 的 EC50 值。米霉 (Xoo) 和米黄单胞菌 pv. oryzicola (Xoc) 分别为 0.59 和 1.63 mg/L，高于噻二唑铜（90.43 和 97.93 mg/L）和双噻唑（68.37 和 75.59 mg/L）。此外，化合物33对细菌性叶斑病（BLS）和细菌性叶枯病（BLB）的保护活性分别为49.65%和49.42%，优于噻二唑铜（44.28%和41.51%）和双噻唑（38.89%和40.09%）。化合物33对BLS的保护活性与防御相关酶活性、叶绿素含量和光合作用激活的提高密切相关。这与防御反应和光合作用相关蛋白的表达上调一致。
A series of novel 6-sulfonyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives were designed and synthesized. CoMFA models were established to analyze the quantitative structure-activity relationships on the basis of the EC50 values of the compounds. The models were used to design and synthesize compounds 32 and 33 with higher activities. The EC50 values of compound 33 against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc) were 0.59 and 1.63 mg/L, respectively, which were higher than those of thiodiazole copper (90.43 and 97.93 mg/L) and bismerthiazol (68.37 and 75.59 mg/L). Moreover, protective activities of compound 33 against bacterial leaf streak (BLS) and bacterial leaf blight (BLB) were 49.65% and 49.42%, respectively, which were superior to those of thiodiazole copper (44.28% and 41.51%) and bismerthiazol (38.89% and 40.09%). Protective activity of compound 33 against BLS was closely related to the improvement of defense-related enzyme activities, chlorophyll content, and photosynthesis activation. This is consistent with the upregulated expression of defense responses and photosynthesis-related proteins.