高等学校化学学报2026，Vol.47Issue(6)：95-104,10.DOI:10.7503/cjcu20250389
泽兰素衍生S-糖苷的高化学和高立体选择性合成及α-葡萄糖苷酶抑制活性
Highly Chemo-and Stereoselective Synthesis of S-Glycosides from Euparin and Their α-Glucosidase Inhibitory Activity
摘要
Abstract
Herein,novel S-glycoside derivative was designed and synthesized using euparin as the aglycone.Employing a palladium-catalyzed strategy,22 S-glycosides were efficiently synthesized under mild conditions with high chemoselectivity and stereoselectivity.Evaluation of the in vitro α-glucosidase inhibitory activities of these compounds showed that compounds 5a,5d,and 7 exhibited potent inhibitory activity,with IC50 values of 2.7,5.7 and 12.1 μmol/L,respectively.Molecular docking studies revealed that these active compounds bind to the active site of α-glucosidase through hydrogen bonds(with ASP382 and HIS326 residues)and π-π stacking interactions(with PHE144 residue),contributing to high binding affinity(docking score:-32.409 kJ/mol).This study provides a mild and efficient synthetic method for euparin-derived S-glycosides and identifies promising lead compounds for the development of novel anti-diabetic drugs.关键词
糖尿病/泽兰素/α-葡萄糖苷酶/S-糖苷/钯催化Key words
Diabetes mellitus/Euparin/α-Glucosidase/S-Glycoside/Palladium catalysis分类
化学化工引用本文复制引用
赵宇,付子帅,张颖,李林轩,刘朝霞,姚辉,黄年玉,王能中..泽兰素衍生S-糖苷的高化学和高立体选择性合成及α-葡萄糖苷酶抑制活性[J].高等学校化学学报,2026,47(6):95-104,10.基金项目
国家自然科学基金(批准号:22207063,22501156)、湖北省中央引导地方科技发展资金(批准号:2024BSB016,2025CSA093)、湖北省自然科学基金(批准号:2025AFD262,2025AFB213)、高等学校学科创新引智计划(批准号:D20015)和天然产物研究与利用湖北省重点实验室(三峡大学)开放基金(批准号:2024NPRD03,2024NPRD04,2024NPRD05,2025NPRD01)资助.Supported by the National Natural Science Foundation of China(Nos.22207063,22501156),the Hubei Provincial Central Government Guided Local Science and Technology Development Project,China(Nos.2024BSB016,2025CSA093),the Hubei Provincial Natural Science Foundation of China(Nos.2025AFD262,2025AFB213),the 111 Project,China(No.D20015)and the Opening Funding of Hubei Key Laboratory of Natural Products Research and Development(China Three Gorges University),China(Nos.2024NPRD03,2024NPRD04,2024NPRD05,2025NPRD01). （批准号:22207063,22501156）
