Full Papers

Synthesis of Novel Bisindolylmaleimide Derivatives

  • Fang Yongbo ,
  • Li Lixiu ,
  • Lu Xingping ,
  • Li Jinhai ,
  • Huang Yan
Expand
  • 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).

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.

Cite this article

Fang Yongbo , Li Lixiu , Lu Xingping , Li Jinhai , Huang Yan . Synthesis of Novel Bisindolylmaleimide Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1303 -1307 . DOI: 10.6023/cjoc1111011

References

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.  
Outlines

/