College of Pharmacy, Shaanxi University of Chinese Medicine, Xi'an/Xianyang, China.
Department of Chemistry, Hong Kong University of Science and Technology, Hong Kong, China.
Bioorg Chem. 2018 Oct;80:253-260. doi: 10.1016/j.bioorg.2018.06.030. Epub 2018 Jun 25.
Series of 1,2,4-triazole Schiff bases (2a-2d, 2f-2h and 3a-3h) have been designed and synthesized. The structure of title compounds was confirmed on the basis of their spectral data and elemental analysis. All the target compounds were screened for their in vitro antifungal activity and antibacterial activity. Two of the tested compounds (2a and 2b) exhibited significant antifungal activity against most fungi, especially compound 2a showed better antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol. The SAR manifested no substitution at position 5 of the triazole ring caused an increase in activity, and 3-phenoxy phenyl group introduced in 1,2,4-triazole scaffold can enhance the antibacterial activity. The DFT calculation indicated triazole ring, S atom and benzene ring in both of the 2a and 3a make a major contribution to the activity.
一系列 1,2,4-三唑席夫碱（2a-2d、2f-2h 和 3a-3h）被设计并合成。根据它们的光谱数据和元素分析，确定了标题化合物的结构。所有目标化合物都进行了体外抗真菌活性和抗菌活性筛选。测试的两种化合物（2a 和 2b）对大多数真菌表现出显著的抗真菌活性，特别是化合物 2a 表现出比三唑酮更好的抗真菌活性。同时，抗菌活性测定也表明化合物 2a 表现出与氯霉素相当的优异抗菌活性。构效关系表明，三唑环 5 位无取代会导致活性增加，而 1,2,4-三唑骨架中引入 3-苯氧基苯基基团可以增强抗菌活性。DFT 计算表明，2a 和 3a 中的三唑环、S 原子和苯环对活性有很大贡献。
