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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1593-1597. 上一篇    下一篇

研究论文

1-氨基-7-甲氧基-β-咔啉及其1-烷氧羰基氨基衍生物的合成和 初步抗肿瘤活性研究

徐广宇*,a   周 伊a   左高磊a  蒋勇军b   

  1. (a湖南师范大学化学化工学院 长沙 410081) (b浙江大学宁波理工学院 宁波 315100)
  • 收稿日期:2008-12-03 修回日期:2009-04-09 发布日期:2009-05-18

Synthesis and Antitumor Activity of 1-Amino-7-methoxy-β-carboline and Its 1-Alkoxycarbonylamino Derivatives

Xu, Guangyu*,a   Zhou, Yi a   Zuo, Gaolei a   Jiang, Yongjunb   

  1. (a College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081) (b Ningbo Institute of Technology, Zhejiang University, Ningbo 315104)
  • Received:2008-12-03 Revised:2009-04-09 Published:2009-05-18

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以1-甲氧羰基-7-甲氧基-β-咔啉为原料经肼解、重氮化反应得1-叠氮酰基-7-甲氧基-β-咔啉(6), 再经Curtius重排、碱解反应得1-氨基-7-甲氧基-β-咔啉(2). 化合物6的Curtius重排产物与各种醇反应得1-烷氧羰基氨基-7-甲氧基-β-咔啉(3). 所得到的10个化合物结构经1H NMR, 13C NMR, MS和元素分析确证. 采用MTT法对合成的化合物进行了体外抗肿瘤活性测定, 结果表明, 在10－5 mol/L浓度下目标化合物具有一定的抗肿瘤活性, 其中化合物3e, 3g和3h对HepG2和SGC-7901抑制率均高于阳性对照物骆驼蓬碱(1).

关键词: 合成, β-咔啉, 1-氨基-7-甲氧基-β-咔啉, 衍生物, 抗肿瘤活性

1-Amino-7-methoxy-β-carboline (2) was synthesized through Curtius rearrangement and alkaline hydrolysis from 1-azidocarbonyl-7-methoxy-β-carboline, which was obtained from 1-methoxycarbonyl- 7-methoxy-β-carboline (4) via hydrazinolysis and diazotization reactions. A series of 1-alkoxycarbony- lamino derivatives 3 of compound 2 were prepared by reaction of 6 in the presence of alkyl alcohol in a re-flux condition. All the compounds were identified by 1H NMR, 13C NMR, MS techniques and elemental analysis. The preliminary antitumor activities were investigated by MTT method and the results show that the synthesized compounds display somewhat antitumor activity at the concentration of 10－5 mol/L. The in-hibition rates of 3e, 3g and 3h against HepG2 and SGC-7901 cells were higher than that of harmine (1), which was used as a positive control drug.

Key words: synthesis, β-carboline, 1-amino-7-methoxy-β-carboline, derivative, antitumor acitivity