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  

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

作　　者：万茂生[1] 何秋霞[2] 赵宝祥[1] 焦培福[1] 王大威[3] 苗俊英[2] 

机构地区：[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

出　　处：《有机化学》2006年第9期1248-1253,共6页Chinese Journal of Organic Chemistry

基　　金：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1HNMR,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.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.

关 键 词：吲哚衍生物 还原 环化 肺癌A549细胞 生长抑制活性 

分 类 号：O626[理学—有机化学]