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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
引用本文:万茂生,何秋霞,赵宝祥,焦培福,王大威,苗俊英.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[J].有机化学,2006,26(9):1248-1253.
作者姓名:万茂生  何秋霞  赵宝祥  焦培福  王大威  苗俊英
作者单位:1. 山东大学化学与化工学院有机化学研究所,济南,250100
2. 山东大学生命科学学院发育生物学研究所,济南,250100
3. 山东省疾病预防控制中心,济南,250014
基金项目:山东省自然科学基金(No.Z2002D05),教育部重点(No.104112)资助项目.
摘    要: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  还原  环化  肺癌A549细胞  生长抑制活性
收稿时间:09 28 2005 12:00AM
修稿时间:03 23 2006 12:00AM

Synthesis and Bioactivity Evaluation of Ethyl 6-Amino-2-substituent- indole-3-carboxylates and Their Derivatives
WAN Mao-Sheng,HE Qiu-Xia,ZHAO Bao-Xiang,JIAO Pei-Fu,WANG Da-Wei,MIAO Jun-Ying.Synthesis and Bioactivity Evaluation of Ethyl 6-Amino-2-substituent- indole-3-carboxylates and Their Derivatives[J].Chinese Journal of Organic Chemistry,2006,26(9):1248-1253.
Authors:WAN Mao-Sheng  HE Qiu-Xia  ZHAO Bao-Xiang  JIAO Pei-Fu  WANG Da-Wei  MIAO Jun-Ying
Institution:a Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100;b Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100;c Shandong Center for Disease Control and Prevention, Jinan 250014
Abstract: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 spec- tra. These compounds were assayed with inhibitory activity against lung cancer A549 cell growth, and the inhibitory effect on the cell viability was dose-dependent.
Keywords:indole derivative  reduction  cyclization  lung cancer cell A549  growth inhibitory activity
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