N-Acetylenethio phthalimides: Sequential linkage for compositional click reaction  

作　　者：Wen-Chao Gao Kai Feng Jun Tian Juan Zhang Hong-Hong Chang Xuefeng Jiang 

机构地区：[1]College of Biomedical Engineering,Taiyuan University of Technology,Taiyuan 030024,China [2]School of Chemistry and Molecular Engineering,East China Normal University,Shanghai 200062,China

出　　处：《Chinese Chemical Letters》2023年第2期183-187,共5页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China (Nos. 21901179 and 22125103);the Scientific Activities of Selected Returned Overseas Professionals of Shanxi Province (No. 20200002);the Natural Science Foundation of Shanxi Province (No. 202103021224067);the Research Project of Shanxi Scholarship Council (No. HGKY2019029)。

摘　　要：Click chemistry has become a useful tool for diverse molecular linkage and modification, and the development of new click strategy that enable reversibility and multifunctionality is of high demand for the multifunction and drug release. Herein, compositionally clicking combined regioselective iridium-catalyzed azide-alkynthio cycloaddition(Ir-AAC) and disulfuration has been developed for the sequential linkage from N-acetylenethio phthalimides, naturally occurring thiols and readily available azides. This method has been successfully applied to the construction of drug hybrids, peptide modification and glycosylation. Furthermore, by the design of diacetylenethio phthalimide as a platform molecule, trifunctional conjugants were sequentially linked through independent Ir-AAC, disulfuration and Cu-AAC reaction for hydrophobic tagging ternary PROTACs.

关 键 词：Diversity-oriented synthesis Compositional click Reversible linkage Iridium catalysis Hydrophobic tagging 

分 类 号：O625.6[理学—有机化学]