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铜催化异硒氰酸酯的多米诺环化反应:一条通往结构多样的硒双杂环和稠合杂环化合物的途径

Copper-Catalyzed Domino Annulation of Isoselenocyanates: A Pathway to Structurally Diverse , Se-Bis-Heterocyclic, and Fused Heterocyclic Compounds.

作者信息

Wang Hai-Yang, Fang Yi-Ling, Wang Ying-Chun, He Yan

机构信息

College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China.

Department of Chemistry and Pharmacy Guilin Normal College, Gulin 541199, People's Republic of China.

出版信息

J Org Chem. 2025 Feb 28;90(8):2937-2949. doi: 10.1021/acs.joc.4c02660. Epub 2025 Jan 10.

DOI:10.1021/acs.joc.4c02660
PMID:39791970
Abstract

A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12-benzo[4,5]selenazole[2,3-]quinazolin-12-one derivatives from isoselenocyanates. This domino reaction efficiently constructed multiple new chemical bonds in a single step, forming either four (one C-Se and three C-) or three (one C-Se and two C-) bonds. The reaction offers several key advantages, including mild conditions, broad substrate compatibility, and straightforward and safe operation. It presents a new method for synthesizing , Se-containing polycyclic compounds, which have potential interest in medicinal chemistry. Notably, some of the synthesized compounds exhibited anticancer activity with IC values below 20 μmol L against T24 human bladder cancer cells.

摘要

开发了一种铜催化的多米诺加成/环化反应,以从异硒氰酸酯合成新型苯并硒唑连接的1,2,3-三唑和四环稠合的12-苯并[4,5]硒唑[2,3 -]喹唑啉-12-酮衍生物。这种多米诺反应在一步中有效地构建了多个新的化学键,形成四个(一个C-Se和三个C-)或三个(一个C-Se和两个C-)键。该反应具有几个关键优点,包括温和的条件、广泛的底物兼容性以及直接且安全的操作。它为合成含硒多环化合物提供了一种新方法,这些化合物在药物化学中具有潜在的研究价值。值得注意的是,一些合成化合物对T24人膀胱癌细胞表现出抗癌活性,IC值低于20μmol/L。

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