Synthesis, Characterization, Antioxidant Activity, and Molecular Docking Studies of Novel Coumarin Selenoether Thiazolylhydrazone Derivatives

doi:10.6023/cjoc202604045

Chinese Journal of Organic Chemistry

ARTICLE

新型香豆素硒醚噻唑腙类衍生物的合成、表征、抗氧化活性及分子对接研究

吝婷婷^a, 付磊清^a, 张伟^b, 王泳^c, 郭孟萍^*,a, 曾春来^*,b

^a宜春学院药学院江西宜春 336000;
^b丽水市人民医院, 温州医科大学附属第六医院浙江丽水 323000;
^c宜春学院基础医学院江西宜春 336000

收稿日期:2026-07-23 修回日期:2026-07-30
基金资助:
江西省教育厅科学技术研究项目重点项目（No.GJJ2201704）资助.

Synthesis, Characterization, Antioxidant Activity, and Molecular Docking Studies of Novel Coumarin Selenoether Thiazolylhydrazone Derivatives

Lin, Tingting^a, Fu, Leiqing^a, Zhang, Wei^b, Wang, Yong^c, Guo, Mengping^*,a, Zeng, Chunlai^*,b

^aSchool of Pharmacy, Yichun University, Yichun, Jiangxi 336000, PR China;
^bLishui People’s Hospital, The Six Affiliated Hospital of Wenzhou Medical University, Lishui, Zhejiang 323000, PR China;
^cSchool of Basic Medicine, Yichun University, Yichun, Jiangxi 336000, PR China

Received:2026-07-23 Revised:2026-07-30
Contact: ^*E-mail:guomengping65@163.com; Zengchunlai@vip.wmu.edu.cn
Supported by:
Key Project of Science and Technology Research of Jiangxi Education Department (No.GJJ2201704).

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Abstract

Coumarin derivatives have attracted significant interest due to their low toxicity and broad-spectrum biological activities. In this study, coumarin selenoether thiazolylhydrazone derivatives were synthesized, and characterized using ¹H NMR, ¹³C NMR, and HRMS. Their in vitro antioxidant capacities were assessed based on their abilities to scavenge DPPH, galvinoxyl, and ABTS⁺radicals. Derivatives 3a-3h demonstrated considerable radical-scavenging activity, with 3a, 3e, and 3f exhibiting superior performance compared to the standard drug ascorbic acid. while ortho‑hydroxy (3e) and meta‑hydroxy (3f) derivatives further improved activity to IC₅₀ values of 7.47/4.62/7.70 and 7.99/7.86/10.25 µmol/L, respectively, highlighting that ortho/meta hydroxyl positioning is the key structural determinant for enhanced antioxidant potency. Cytotoxicity was evaluated on RAW 264.7 macrophages using the CCK-8 assay, revealing low cytotoxicity for 3a, 3e, and 3f. Their antioxidant protective effects in RAW 264.7 cells were evaluated using an H₂O₂-induced oxidative injury model. 2',7'-Dichlorodihydrofluorescein diacetate (DCFH-DA) assays revealed that 3a, 3e, and 3f markedly reduced ROS levels in oxidative injury cells. The molecular docking study targeting the active site of human peroxiredoxin 5 (PDB ID: 1HD2) was performed to investigate the potential interactions of 3a, 3e, and 3f with the protein receptor. The results revealed that the mainly binding modes of them was hydrogen bond. In conclusion, these findings suggest that 3a, 3e, and 3f possess promising antioxidant properties and warrant further investigation and development.

Key words: Coumarin, selenoether, Thiazolylhydrazone, Synthesis, Antioxidant, Cytotoxicity, Molecular docking

Cite this article

Lin, Tingting, Fu, Leiqing, Zhang, Wei, Wang, Yong, Guo, Mengping, Zeng, Chunlai. Synthesis, Characterization, Antioxidant Activity, and Molecular Docking Studies of Novel Coumarin Selenoether Thiazolylhydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604045.

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新型香豆素硒醚噻唑腙类衍生物的合成、表征、抗氧化活性及分子对接研究

Synthesis, Characterization, Antioxidant Activity, and Molecular Docking Studies of Novel Coumarin Selenoether Thiazolylhydrazone Derivatives

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