Citation: Zhang Chenglu, Wang Huayu, Yu Xiangkun, Yang Jingyi, Li Chuanyin, Gong Rongqin, Song Fulu, Sun Yuedong. Synthesis of Amide Thioether Bridged 1, 3-Selenazole and 1, 2, 4-Triazole Derivatives and Their Inhibitory Activity against Cell Division Cycle Phosphatase B (Cdc25B)[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 432-439. doi: 10.6023/cjoc201907020 shu

Synthesis of Amide Thioether Bridged 1, 3-Selenazole and 1, 2, 4-Triazole Derivatives and Their Inhibitory Activity against Cell Division Cycle Phosphatase B (Cdc25B)

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Corresponding author: Zhang Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 14 July 2019
Revised Date: 27 September 2019
Available Online: 12 February 2019
Fund Project: Project supported by the Science and Technology Research Program of Liaoning Provincial Department of Education (No. 2009A426)the Science and Technology Research Program of Liaoning Provincial Department of Education 2009A426

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The cell division cycle 25 phosphatase B (Cdc25B) is involved in carcinogenic transformation and is a potential drug target for anticancer therapy. In order to screen Cdc25B inhibitors, 1, 3-selenazole was selected as the core block, and 1, 2, 4-triazole Schiff base was bridged into 2-(1, 2, 4-triazol-3-yl)thio-N-(4-phenyl-1, 3-selenazolyl-2-yl)acetamide (TATS) by the amide thioether bond. The molecular docking simulation of TATS1 with Cdc25B was first performed to identify the rationality of the core function of 1, 3-selenazole. The results show that 1, 3-selenazole can be tightly embedded in the Cdc25B structure and perform N-H…PI non-bond weak interaction with the important catalytic site Arg492, which indicates that 1, 3-selenazole plays a central role. The amide carbonyl oxygen atom forms a hydrogen bond with Arg492 and Arg488, indicating that the introduction of the amide thioether bond is reasonable. Based on the theoretical docking study, thirteen new target compounds TATS1~TATS13 were designed and synthesized through modification in two regions of 1, 2, 4-triazole Schiff base. The inhibition against Cdc25B of target molecules and important intermediates was tested respectively. As a result, the inhibitory activities of the intermediates are not good, 12 target compounds have better biological activity than the positive reference substance Na₃VO₄, the modifications of two regions of 1, 2, 4-triazole also have a significant effect, which suggests that these compounds are expected to be a potential inhibitor of Cdc25B.
- 1, 3-selenazole,
- 1, 2, 4-triazole Schiff base,
- molecular docking simulation,
- Cdc25B inhibitor
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