Sui Jingzhi, He Yun, Wang Ding, Wang Tao, Ren Kexin, Liang Yong, Zhang Zunting
Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710119, China.
Department of Molecular Medicine, Beckman Research Institute of City of Hope, Duarte, CA, 91010, USA.
Mol Divers. 2025 Feb;29(1):367-378. doi: 10.1007/s11030-024-10857-1. Epub 2024 Apr 21.
A concise method for the synthesis of cis-(8b,14a)-hexahydro-14H-dibenzo[f,h]oxazolo[3,2-b]isoquinolin-14-ones 2 via photo-induced 3-([1,1'-biphenyl]-2-yl)-1-(2-hydroxyethyl)pyridin-2(1H)-ones 1 was developed. Irradiation of 1 in the solution of toluene with a 313 nm UV light in the presence of HCl gave cis-(8b,14a)-9a-α-hexahydro-14H-dibenzo[f,h]oxazolo[3,2-b]isoquinoli n-14-ones and cis-(8b,14a)-9a-β-hexahydro-14H-dibenzo[f,h]oxazolo[3,2-b]isoquinolin-14-ones 2 (2-α and 2-β) in good yields. The protocol simultaneously constructs dearomatized phenanthrene ring and oxindolizidinones ring by photo cascade reaction to achieve high bonding efficiency and high atomic efficiency. Additionally, the antitumor activities of 2 was evaluated and compounds 2b-α, 2b-β, 2j-β and 2 k-α showed similar or better activity compared to the cisplatin against tumor cell lines of Leukemia HL-60, lung cancer A594, liver cancer SMMC-7721 and breast cancer MDA-MB-231.
开发了一种通过光诱导的3-([1,1'-联苯]-2-基)-1-(2-羟乙基)吡啶-2(1H)-酮1合成顺式-(8b,14a)-六氢-14H-二苯并[f,h]恶唑并[3,2-b]异喹啉-14-酮2的简洁方法。在HCl存在下，用313 nm紫外光照射甲苯溶液中的1，可得到顺式-(8b,14a)-9a-α-六氢-14H-二苯并[f,h]恶唑并[3,2-b]异喹啉-14-酮和顺式-(8b,14a)-9a-β-六氢-14H-二苯并[f,h]恶唑并[3,2-b]异喹啉-14-酮2（2-α和2-β），产率良好。该方案通过光级联反应同时构建了去芳构化的菲环和羟吲哚嗪酮环，以实现高键合效率和高原子效率。此外，还评估了2的抗肿瘤活性，化合物2b-α、2b-β、2j-β和2k-α对白血病HL-60、肺癌A594、肝癌SMMC-7721和乳腺癌MDA-MB-231肿瘤细胞系的活性与顺铂相似或更好。
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