含1,2,3,4-四氢异喹啉片段磺酰肼和酰肼类化合物的设计、合成及生物活性研究
Chinese Journal of Organic Chemistry(2023)
Abstract
In order to find agricultural fungicide candidates with lassase as potential target, 14 unreported sulfonyl hydrazide and 9 hydrazide derivatives were designed and synthesized by replacing tetrahydroquinoline skeleton of the lead compound 4-methyl-N'-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl)benzenesulfonohydrazide (4bg) with active fragment 1,2,3,4-tetra-hydroisoquinoline. The structures of the target compounds were confirmed by H-1 NMR, C-13 NMR and HRMS. The in vitro bioassay showed that 2-methyl-N'-(1,2,3,4-tetrahydroisoquinoline-2-carbonothioyl)benzenesulfonohydrazide (4b) showed excellent fungicidal activity against V. Mali and S. sclerotiorum with EC50 values of 4.81 and 1.57 mu g/mL, respectively, which were better than that of lead compound 4bg. In addition, 5-methyl-N'-(1,2,3,4-tetrahydroisoquinoline-2-carbonothioyl)pyrazine2-carbohydrazide (5i) showed good broad-spectrum fungicidal activity against V. Mali, S. sclerotiorum, B. cinerea, M. oryzae and F. graminearum with EC50 range of 12.88 similar to 28.65 mu g/mL. Moreover, compounds 4b and 5i exhibited moderate laccase inhibitory activity (37.07%, 35.49%), which were similar to that of cysteine (43.10%) at 50 mu g/mL. Furthermore, the binding modes of compounds 4b and 5i with laccase protein were simulated by molecular docking method, which provided guidance for further modification of compounds.
MoreTranslated text
Key words
laccase inhibitor,1,2,3,4-tetrahydroisoquinoline,(sulfonyl) hydrazide,fungicidal activity,molecular docking
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined