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2012 , Vol. 32 >Issue 07: 1303 - 1307

DOI: https://doi.org/10.6023/cjoc1111011

研究论文

新型双吲哚马来酰亚胺衍生物的合成

  • 方勇波 ,
  • 李丽秀 ,
  • 卢杏萍 ,
  • 黎金海 ,
  • 黄雁
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  • 广州医学院基础学院 广州 510182

收稿日期: 2011-11-01

  修回日期: 2012-01-19

  网络出版日期: 2012-03-09

基金资助

广东省科技计划(No. 2008B060600074)及广州市属高校科技计划(No. 08A107)资助项目.

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Synthesis of Novel Bisindolylmaleimide Derivatives

  • Fang Yongbo ,
  • Li Lixiu ,
  • Lu Xingping ,
  • Li Jinhai ,
  • Huang Yan
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  • School of Basic Science, Guangzhou Medical College, Guangzhou 510182

Received date: 2011-11-01

  Revised date: 2012-01-19

  Online published: 2012-03-09

Supported by

Project supported by the Guangdong Provincial Program of Science and Technology (No. 2008B060600074) and the Guangzhou Municipal University Program of Science and Technology (No. 08A107).

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摘要

以1-(3-氧代四氢吡喃丙基)-吲哚-3-乙醛酸甲酯5和吲哚-3-乙酰胺6为原料, 在催化剂叔丁醇钾的四氢呋喃溶液存在下发生偶合反应, 经浓盐酸处理得脱保护的中间体7, 再经甲磺酰化反应、氨解反应得到4 种新的具有不同氨烷基侧链的双吲哚马来酰亚胺衍生物9a, 9b, 9d, 9e. 目标产物结构通过1H NMR, 13C NMR, MS 和HRMS 确证.

关键词： 双吲哚马来酰亚胺; 衍生物; 合成

本文引用格式

方勇波 , 李丽秀 , 卢杏萍 , 黎金海 , 黄雁 . 新型双吲哚马来酰亚胺衍生物的合成[J]. 有机化学, 2012 , 32(07) : 1303 -1307 . DOI: 10.6023/cjoc1111011

Abstract

Four novel bisindolylmaleimides 9a,9b,9d,9e containing different aminoalkyl side chains were derived from methylsulfonylation, ammonolysis of the intermediate 7, which was prepared by reaction of methyl[1-(3-O’-tetrahydropyranepropyl)indolyl-3]-glyoxylate (5) with indole-3-acetamides (6) using t-BuOK in THF as catalyst and treatment using concentrated hydrochloric acid subsequently.The structures of target products were also confirmed by 1H NMR,13C NMR, MS,HRMS techniques.

Key words： Bisindolylmaleimide; Derivatives; Synthesis

参考文献

1 (a) Alexandra, C. N. J. Biol. Chem. 1995, 270, 28495. (b) Mellor, H.; Parker P. J. Biochem. J. 1998, 332(Pt 2), 281.
2 (a) Koivunen, J.; Aahonen, V.; Pehonen, J. Cancer Lett. 2006, 235, l. (b) Patel, N. A.; Song, S.S.; Cooper, D. R.. Gene Expr. 2006, 13, 73. (c) Ishii, H.; Jirousek, M. R.; Koya, D.; Takagi, C.; Xia, P.; Clermont, A.; Bursell, S.-E.; Kern, T. S.; Ballas, L. M.; Heath, W. F.; Stramm, L. E.; Feener, E. P.; King, G. L. Science. 1996, 272, 728 (d) Jirousek, M. R.; Gillig, J. R.; Gonzalez, C. M.; Heath, W. F.; McDonald J. H.; Neel, D. A.; Rito, C. J.; Singh, U.; Stramm, L. E.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L. M.; Hall, S. E.; Winneroski, L. L.; Faul, M. M. J. Med. Chem. 1996, 39, 2664.  
3 (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchya, H.; Takahashi, Y.; Masuma, R. J. Antibiotics. 1977, 30, 275. (b) Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. J. Chem. Soc. Chem. Commun. 1978, 800. (c) Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jap. 1982, 55, 3681.  
4 (a) Tamaoki, T.; Nomoto, H.; Takahashi, I.; Kato, Y.; Morimoto, M.; Tomita, F. Biochem. Biophys. Res. Commun. 1986, 135, 397. (b) Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535. (c) Davis, P. D.; Hill, C. H.; Keech, E.; Lawton, G.; Nixon, J. S.; Sedgwick, A. D.; Wadsworth, J.; Westmacott, D.; Wilkinson, S. E. FEBS Letts. 1989, 259, 61.  
5 (a) Toullec, D.; Pianetti, P.; Coste, H.; Bellevergue, P.; Grand-Perret, T.; Ajakane, M.; Baudet, V.; Boissin, P.; Boursier, E.; Loriolle, F.; Duhamel, L.; Charon, D.; Kirilovsky, J. J. Biol. Chem. 1991, 266, 15771. (b) Davis, P. D.; Hill, C. H.; Lawton,G.; Nixon, J. S.; Wilkinson, S. E.; Hurst, S. A.; Keech, E.; Turner, S. E. J. Med. Chem. 1992, 35, 177. (c) Zhao, S.-Y.; Shao, Z.-Y.; Qin, W.-M.; Zhang, D.-Q. Chin. J. Org. Chem. 2008, 28, 1676(in Chinese). (赵圣印, 邵志宇, 钦维民, 张灯青, 有机化学, 2008, 28, 1676.) (d) Fan, M.; Xie, Z.-X.; Xu, Z.-H.; Ping, B.; Zhao, S.-Y. Chin. J. Org. Chem. 2011, 31, 843(in Chinese). (范梅, 谢志雄, 徐之涵, 平冰, 赵圣印, 有机化学, 2011, 31, 843.)
6 Davis,P.D.;Elliott,L.;Harris,W.;Hill,C.H.;Hurst,S.A.;Keech, E.; Kumar, H.; Lawton, G.; Nixon, J. S.; Wilkinson, S. E. J. Med. Chem. 1992, 35, 994.  
7 (a) Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053. (b) Smaill, J. B.; Baker, E. N.; Booth, R. J.; Bridges, A. J.; Dickson, J. M.; Dobrusin, E. M.; Ivanovic, I.; Kraker, A. J.; Lee, H. H.; Lunney, E. A.; Ortwine, D. F.; Palmer, B. D.; Quin J. Ⅲ; Squire, C. J.; Thompson, A. M.; Denny, W. A. Eur. J. Med. Chem. 2008, 43, 1276.
8 (a) Chen, N.-L. Solvents Handbook, 2nd ed., Chemical Industry Press, Beijing, 1944 (in Chinese). (程能林, 溶剂手册(第二版), 化学工业出版社, 北京, 1994.) (b) Miyashita, M.; Yoshikoshi, A..; Griecolb. P. A. J. Org. Chem. 1977, 42, 3772.  
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