Citation: Zhang Xiaoming, Lei Peng, Li Xinlu, Yang Xinling, Zhang Xuebo, Sun Tengda, Ling Yun. Synthesis and Anti-fungual Activity of Novel Aspernigerin Derivatives Containing Thiocarbonyl Moiety[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3197-3203. doi: 10.6023/cjoc201807004 shu

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

Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193

Corresponding author: Ling Yun, lyun@cau.edu.cn
Received Date: 2 July 2018
Revised Date: 24 July 2018
Available Online: 5 December 2018
Fund Project: the National Natural Science Foundation of China 21472236Project supported by the National Natural Science Foundation of China (No. 21472236)

Figures(4)

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).
- natural product,
- aspernigerin,
- tetrahydroquinoline,
- synthesis,
- anti-fungal activity
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