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PhICl介导的-(1-炔基)苯甲酸酯的区域选择性和亲电氧硫/硒氰化反应:合成具有生物活性的含S/SeCN异香豆素

PhICl-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of -(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins.

作者信息

Tao Shanqing, Huo Aiwen, Gao Yan, Zhang Xiangyang, Yang Jingyue, Du Yunfei

机构信息

Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China.

Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao, China.

出版信息

Front Chem. 2022 May 18;10:859995. doi: 10.3389/fchem.2022.859995. eCollection 2022.

Abstract

The application of PhICl/NHSCN and PhICl/KSeCN reagent systems to the synthesis of the biologically active S/SeCN-containing isocoumarins a process involving thio/selenocyanation, enabled by thio/selenocyanogen chloride generated , followed with an intramolecular lactonization was realized. Gram-scale synthesis, further derivatization to access C4 thio/selenocyanated Xyridin A and anti-tumor activities of the obtained products highlight the potential use of this method.

摘要

PhICl/NHSCN和PhICl/KSeCN试剂体系在生物活性含S/SeCN异香豆素合成中的应用——一个涉及硫/硒氰化的过程,该过程由生成的硫/硒氰化氯引发,随后进行分子内内酯化反应得以实现。克级规模的合成、进一步衍生化以获得C4硫/硒氰化的Xyridin A以及所得产物的抗肿瘤活性突出了该方法的潜在用途。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6c6/9158338/474540fcabc0/fchem-10-859995-g001.jpg

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