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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (9): 1248-1253. 上一篇    下一篇

研究论文

6-氨基-2-取代吲哚-3-羧酸乙酯及其衍生物的合成与生物活性评价

万茂生a，何秋霞b，赵宝祥*,a，焦培福a，王大威c，苗俊英*,b   

  1. (a山东大学化学与化工学院有机化学研究所 济南 250100)
    (b山东大学生命科学学院发育生物学研究所 济南 250100)
    (c山东省疾病预防控制中心 济南250014)
  • 收稿日期:2005-09-28 修回日期:2006-02-14 发布日期:2006-09-11
  • 通讯作者: 苗俊英

Synthesis and Bioactivity Evaluation of Ethyl 6-Amino-2-substituent- indole-3-carboxylates and Their Derivatives

WAN Mao-Shenga,HE Qiu-Xiab,ZHAO Bao-Xiang*,a
JIAO Pei-Fua,WANG Da-Weic,MIAO Jun-Ying*,b   

  1. (a Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100)
    (b Institute of Developmental Biology, School of Life Sci-ence, Shandong University, Jinan 250100)
    (c Shandong Center for Disease Control and Prevention, Jinan 250014)
  • Received:2005-09-28 Revised:2006-02-14 Published:2006-09-11
  • Contact: MIAO Jun-Ying

PDF

906

被引次数

48 | 6

以2,4-二硝基氯苯和乙酰乙酸乙酯为原料, 经过亲核置换、还原-环化协同反应, 合成了6-氨基-2-甲基吲哚-3-羧酸乙酯, 而后在催化剂作用下, 与乙酰乙酸乙酯反应生成烯胺, 环化合成9-羟基-2,7-二甲基吡咯(2,3-f)喹啉-3-羧酸乙酯; 类似地, 合成了6-氨基-2-苯基吲哚-3-羧酸乙酯和6-氨基-2-(呋喃-2'-基)吲哚-3-羧酸乙酯. 其结构均由1H NMR, IR以及MS波谱数据表征. 所得化合物具有抑制肺癌A549细胞生长的活性, 其抑制效果具有浓度依赖性.

关键词: 吲哚衍生物, 生长抑制活性, 还原, 肺癌A549细胞, 环化

Ethyl 6-amino-2-substituent-indole-3-carboxylate was synthesized via SNAr reaction, reduction and tandem cyclization from 2,4-dinitrochlorobenzene and ethyl acetoacetate. The reaction of ethyl 6-amino-2-methylindole-3-carboxylate with ethyl acetoacetate in the presence of catalyst gave an enamine compound, and then ethyl 9-hydroxy-2,7-dimethylpyrrolo(2,3-f)quinoline-3-carboxylate was obtained by cyclization. Similarly, ethyl 6-amino-2-phenylindole-3-carboxylate and ethyl 6-amino-2-fur-2'-ylindole-3- carboxylate were synthesized. The structures of compounds were determined by 1H NMR, IR and MS spectra. These compounds were assayed with inhibitory activity against lung cancer A549 cell growth, and the inhibitory effect on the cell viability was dose-dependent.

Key words: reduction, growth inhibitory activity, cyclization, lung cancer cell A549, indole derivative