Wang Hai-Yang, Fang Yi-Ling, Wang Ying-Chun, He Yan
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.
J Org Chem. 2025 Feb 28;90(8):2937-2949. doi: 10.1021/acs.joc.4c02660. Epub 2025 Jan 10.
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.
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。