摘要/Abstract

基于天然产物Aspernigerin的结构特征，设计合成了一系列含有硫羰基结构的新型四氢喹啉类化合物.化合物结构均经过¹H NMR，¹³C NMR，HRMS确证，用X射线单晶衍射测定了（E）-3-（4-氟苯基）-1-[4-（1，2，3，4-四氢喹啉-1-羰基）哌嗪-1-基]丙-2-烯-1-酮（5j）的晶体结构.并对目标化合物的抑菌活性进行了研究.离体真菌抑制活性结果表明，部分目标化合物显示出较好的生物活性，其中（E）-1-[4-（1，2，3，4-四氢喹啉-1-羰基）哌嗪-1-基]-3-（邻甲苯基）丙-2-烯-1-酮（5b）对苹果腐烂病菌的抑制活性（EC₅₀=3.04 μg/mL）优于对照药剂氟酰胺（EC₅₀=9.16 μg/mL），可作为二级先导进行进一步的优化研究.
关键词: 天然产物, Aspernigerin, 四氢喹啉, 合成, 抗真菌活性
Based on the structure of natural product aspernigerin, a series of novel tetrahydroquinoline compounds containing thiocarbonyl moiety were designed and synthesized. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS, and the crystal structure of (E)-3-(4-fluorophenyl)-1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl) piperazin-1-yl)prop-2-en-1-one (5J) was determined by X-ray single crystal diffraction. The bioassay results indicated that (E)-1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonothioyl)piperazin-1-yl)-3-(o-tolyl)prop-2-en-1-one (5b) exhibited good anti-fungual activity against Valsa mali (EC₅₀=3.04 μg/mL), which was better than the commercial fungicide fluoramide (EC₅₀=9.16 μg/mL).
Key words: natural product, aspernigerin, tetrahydroquinoline, synthesis, anti-fungal activity


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