Citation: Zhang Xuebo, Ma Hangyu, Sun Tengda, Lei Peng, Yang Xinling, Zhang Xiaoming, Ling Yun. Design, Synthesis and Fungicidal Activity of Novel Piperidine Containing Cinnamaldehyde Thiosemicarbazide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2965-2972. doi: 10.6023/cjoc201903031 shu

Design, Synthesis and Fungicidal Activity of Novel Piperidine Containing Cinnamaldehyde Thiosemicarbazide Derivatives

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

Corresponding author: Ling Yun, lyun@cau.edu.cn
Received Date: 17 March 2019
Revised Date: 18 April 2019
Available Online: 21 October 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21672258)the National Natural Science Foundation of China 21672258

Figures(6)

In order to find new lead compound with higher fungicidal activity, a series of novel cinnamaldehyde thio-semicarbazone derivatives were designed and synthesized according to scaffold hopping strategy, based on the lead of the thiosemicarbazide derivatives containing piperidine discovered in our preliminary studies. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR, elemental analysis or HRMS. The bioassay results indicated that some compounds exhibited excellent fungicidal activities. In particular, N'-((1E, 2E)-3-(4-chlorophenyl)allylidene)piperidine-1-carbothiohydrazide (3a) and N'-((1E, 2E)-3-phenylallylidene)piperidine-1-carbothiohydrazide (3p) showed above 95% inhibitory rate against Cytospora sp, S. sclerotiorum, P. aphanidermatum and T. cucumeris at 50 μg/mL with EC₅₀ values lower than 10 μg/mL. The preliminary structure-activity relationship indicated that cinnamaldehyde contributes more to the bioactivity than benzaldehyde.
- natural product,
- cinnamyl aldehyde,
- thiosemicarbazide,
- synthesis,
- fungicidal activity
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