新型含硫羰基结构的Aspernigerin衍生物的合成及抑菌活性研究
收稿日期: 2018-07-02
修回日期: 2018-07-24
网络出版日期: 2018-09-05
基金资助
国家自然科学基金（No.21472236）资助项目.
Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety
Received date: 2018-07-02
Revised date: 2018-07-24
Online published: 2018-09-05
Supported by
Project supported by the National Natural Science Foundation of China (No. 21472236).
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
张晓鸣 , 雷鹏 , 李欣潞 , 杨新玲 , 张学博 , 孙腾达 , 凌云 . 新型含硫羰基结构的Aspernigerin衍生物的合成及抑菌活性研究[J]. 有机化学, 2018 , 38(12) : 3197 -3203 . DOI: 10.6023/cjoc201807004
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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