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Two-Step Synthesis of Some Novel Monoindolylmaleimides
Corresponding Author(s) : Qing Ye
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
Monoindolylmaleimides have been identified as potent glycogen synthase kinase-3b inhibitors. In this paper, a convenient methodology for the preparation of some new monoindolylmaleimides was developed by microwave assisted condensation of substituted monochloromaleimides with N-containing heterocycles followed by ammonolysis in good overall yield (up to 80 %). The products were characterized by 1H NMR and ESI-MS.
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- T.A. Engler, J.R. Henry, S. Malhotra, B. Cunningham, K. Furness, J. Brozinick, T.P. Burkholder, M.P. Clay, J. Clayton, C. Diefenbacher, E. Hawkins, P.W. Iversen, Y. Li, T.D. Lindstrom, A.L. Marquart, J. McLean, D. Mendel, E. Misener, D. Briere, J.C. O’Toole, W.J. Porter, S. Queener, J.K. Reel, R.A. Owens, R.A. Brier, T.E. Eessalu, J.R. Wagner, R.M. Campbell and R. Vaughn, J. Med. Chem., 47, 3934 (2004); doi:10.1021/jm049768a.
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- H.C. Zhang, C.K. Derian, D.F. McComsey, K.B. White, H. Ye, L.R. Hecker, J. Li, M.F. Addo, D. Croll, A.J. Eckardt, C.E. Smith, Q. Li, W.M. Cheung, B.R. Conway, S. Emanuel, K.T. Demarest, P. Andrade-Gordon, B.P. Damiano and B.E. Maryanoff, J. Med. Chem., 48, 1725 (2005); doi:10.1021/jm049478u.
- L. Kim and A.R. Kimmel, Curr. Opin. Genet. Dev., 10, 508 (2000); doi:10.1016/S0959-437X(00)00120-9.
- A.S. Wagman and J.M. Nuss, Curr. Pharm. Des., 7, 417 (2001); doi:10.2174/1381612013397915.
- P. Cohen, Eur. J. Biochem., 268, 5001 (2001); doi:10.1046/j.0014-2956.2001.02473.x.
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- A. Castro and A. Martinez, Exp. Opin. Ther. Pat., 10, 1519 (2000); doi:10.1517/13543776.10.10.1519.
- Q. Ye, M. Li, Y. Zhou, T. Pang, L. Xu, J. Cao, L. Han, Y. Li, W. Wang, J. Gao and J. Li, Molecules, 18, 5498 (2013); doi:10.3390/molecules18055498.
- Q. Ye, M. Li, Y.-B. Zhou, J.-Y. Cao, L. Xu, Y.-J. Li, L. Han, J.-R. Gao, Y.-Z. Hu and J. Li, Arch. Pharm. (Weinheim), 346, 349 (2013); doi:10.1002/ardp.201300008.
- X.H. Liu, J.Q. Weng and C.X. Tan, Asian J. Chem., 23, 4064 (2011).
- X.H. Liu, J.Q. Weng, C.X. Tan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011).
References
T.A. Engler, J.R. Henry, S. Malhotra, B. Cunningham, K. Furness, J. Brozinick, T.P. Burkholder, M.P. Clay, J. Clayton, C. Diefenbacher, E. Hawkins, P.W. Iversen, Y. Li, T.D. Lindstrom, A.L. Marquart, J. McLean, D. Mendel, E. Misener, D. Briere, J.C. O’Toole, W.J. Porter, S. Queener, J.K. Reel, R.A. Owens, R.A. Brier, T.E. Eessalu, J.R. Wagner, R.M. Campbell and R. Vaughn, J. Med. Chem., 47, 3934 (2004); doi:10.1021/jm049768a.
I.N. Gaisina, F. Gallier, A.V. Ougolkov, K.H. Kim, T. Kurome, S. Guo, D. Holzle, D.N. Luchini, S.Y. Blond, D.D. Billadeau and A.P. Kozikowski, J. Med. Chem., 52, 1853 (2009); doi:10.1021/jm801317h.
H.C. Zhang, C.K. Derian, D.F. McComsey, K.B. White, H. Ye, L.R. Hecker, J. Li, M.F. Addo, D. Croll, A.J. Eckardt, C.E. Smith, Q. Li, W.M. Cheung, B.R. Conway, S. Emanuel, K.T. Demarest, P. Andrade-Gordon, B.P. Damiano and B.E. Maryanoff, J. Med. Chem., 48, 1725 (2005); doi:10.1021/jm049478u.
L. Kim and A.R. Kimmel, Curr. Opin. Genet. Dev., 10, 508 (2000); doi:10.1016/S0959-437X(00)00120-9.
A.S. Wagman and J.M. Nuss, Curr. Pharm. Des., 7, 417 (2001); doi:10.2174/1381612013397915.
P. Cohen, Eur. J. Biochem., 268, 5001 (2001); doi:10.1046/j.0014-2956.2001.02473.x.
C. Sasaki, T. Hayashi, W.R. Zhang, H. Warita, Y. Manabe, K. Sakai and K. Abe, Neurol. Res., 23, 588 (2001); doi:10.1179/016164101101199054.
A. Castro and A. Martinez, Exp. Opin. Ther. Pat., 10, 1519 (2000); doi:10.1517/13543776.10.10.1519.
Q. Ye, M. Li, Y. Zhou, T. Pang, L. Xu, J. Cao, L. Han, Y. Li, W. Wang, J. Gao and J. Li, Molecules, 18, 5498 (2013); doi:10.3390/molecules18055498.
Q. Ye, M. Li, Y.-B. Zhou, J.-Y. Cao, L. Xu, Y.-J. Li, L. Han, J.-R. Gao, Y.-Z. Hu and J. Li, Arch. Pharm. (Weinheim), 346, 349 (2013); doi:10.1002/ardp.201300008.
X.H. Liu, J.Q. Weng and C.X. Tan, Asian J. Chem., 23, 4064 (2011).
X.H. Liu, J.Q. Weng, C.X. Tan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011).