合成子
化学
呋喃
亲核细胞
细胞凋亡
试剂
环加成
衍生化
基础(拓扑)
体外
立体化学
组合化学
高效液相色谱法
有机化学
生物化学
催化作用
数学
数学分析
作者
Dehao Duan,Yifei Wei,Tianyou Li,Quan Gong,Min Shen,Feng Zhu,Shenglan Liu,Dong‐Nai Ye,Xiangjun Peng
标识
DOI:10.1021/acs.joc.4c00478
摘要
Divergent synthesis of structurally different products from the same kinds of starting materials is highly synthetically useful but very challenging. Herein, we reported a base-mediated chemodivergent [4 + 1] and [2 + 1] cycloaddition of N-alkylpyridinium and enone under mild conditions, leading to furan-fused bicycles with high diastereoselectivity and spirobicycles, respectively, from moderate to high yields. N-Alkylpyridinium salts were modular nucleophilic transfer reagents and C1 synthons, which underwent tandem Michael addition to the α,β-unsaturated ketones and cyclization under the base conditions. Late-stage derivatization of 4-propyldicyclohexylanone from an important industrial raw of liquid crystal display (LCD) screens was realized. In vitro, compound 3f exhibited good activities against human colon cancer cells (HCT116) with IC50 values in 9.82 ± 0.27 μM. Further biological evaluations investigated the mechanism of the effective inhibition of cell growth, including apoptosis ratio detection, cell cycle analysis, and migration capacity of HCT116 cells. In apoptosis effect studies, complex 3f increased the percentage of apoptotic HCT116 cells to 26.8% (15 μM).
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