Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2965-2972.DOI: 10.6023/cjoc201903031 Previous Articles     Next Articles

NOTES

新型哌啶基肉桂醛缩氨基硫脲衍生物的设计、合成及抑菌活性研究

张学博, 马航宇, 孙腾达, 雷鹏, 杨新玲, 张晓鸣, 凌云*()   

  1. 中国农业大学理学院 应用化学系 北京 100193
  • 收稿日期:2019-03-17 修回日期:2019-04-18 出版日期:2019-10-25 发布日期:2019-05-21
  • 通讯作者: 凌云 E-mail:lyun@cau.edu.cn
  • 基金资助:
    国家自然科学基金(No. 21672258)

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

Zhang, Xuebo, Ma, Hangyu, Sun, Tengda, Lei, Peng, Yang, Xinling, Zhang, Xiaoming, Ling, Yun*()   

  1. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
  • Received:2019-03-17 Revised:2019-04-18 Online:2019-10-25 Published:2019-05-21
  • Contact: Ling, Yun E-mail:lyun@cau.edu.cn
  • Supported by:
    Project supported by the National Natural Science Foundation of China(No. 21672258)

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.

Key words: natural product, cinnamyl aldehyde, thiosemicarbazide, synthesis, fungicidal activity