新型含硫羰基结构的Aspernigerin衍生物的合成及抑菌活性研究

Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety

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, ^(13)C 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(EC_(50)=3.04μg/mL)优于对照药剂氟酰胺(EC_(50)=9.16μg/mL),可作为二级先导进行进一步的优化研究.

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, 13 C 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 antifungual activity against Valsa mali(EC50=3.04 μg/mL), which was better than the commercial fungicide fluoramide(EC50=9.16 μg/m L).