Citation: Sun Xiaoyang, Feng Jiajia, Li Shengbin, Feng Siran, Liu Zhenming, Song Yali, Qiao Xiaoqiang. Design, Synthesis, and Antifungal Activity of Novel Thiochromanone Derivatives Containing 1, 3, 4-Oxadiazole Skeleton[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1037-1043. doi: 10.6023/cjoc201808016 shu

Design, Synthesis, and Antifungal Activity of Novel Thiochromanone Derivatives Containing 1, 3, 4-Oxadiazole Skeleton

a.
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmacy, Heibei University, BaoDing 071000
b.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Heibei University, BaoDing 0710004
c.
Drug Design Center, State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191

Corresponding author: Song Yali, yalisong@hbu.edu.cn Qiao Xiaoqiang, xiaoqiao@hbu.edu.cn
Received Date: 16 August 2018
Revised Date: 13 November 2018
Available Online: 28 April 2018
Fund Project: the Natural Science Foundation of Hebei Province B2018201269the National Natural Science Foundation of China 21675039Project supported by the Natural Science Foundation of Hebei Province (No. B2018201269), the National Natural Science Foundation of China (No. 21675039), the China Postdoctoral Science Foundation (No. 2016M591401), the Young Talent of Hebei Province, and the Hebei University Science Fund for Distinguished Young Scholars (No. 2015JQ06)the China Postdoctoral Science Foundation 2016M591401the Young Talent of Hebei Province, and the Hebei University Science Fund for Distinguished Young Scholars 2015JQ06

Figures(5)

Following the principle of union of active group, the thiochromanone was combined with 1, 3, 4-oxadiazole, and 12 compounds were designed and synthesized. The target compounds were confirmed by 1H NMR and HRMS. The preliminary antifungal activity assay showed that most of the target compounds exhibited significant inhibition activity against four animal pathogenic fungi and four plant pathogenic fungi. Among them, the minimum inhibitory concentration (MIC) value of compound 4f against Canidia albicans reached 4 μg·mL^-1, and the MIC value of 4d against Aspergillusnigervan tiegh reached 8 μg·mL^-1, which were higher than the positive controls. And the molecular docking studies have found that 4f has strong binding ability to CYP51 of Canidia albicans, which may be a potential CYP51 inhibitor.
- thiochromanone,
- 1, 3, 4-oxadiazole,
- antifungal,
- molecular docking
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