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Synthesis of Novel Glycosyl Imidazolidine-2,4,5-Trione Derivatives
Corresponding Author(s) : Wei Wei Liu
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
A series of glycosyl imidazolidine-2,4,5-trione derivatives were achieved by condensing per-O-acetylated glucosamine, triphosgene, amines and oxalyl chloride. The convenient and efficient method afforded the desired products with good to excellent yields and the described compounds were prepared for the first time in this work. Satisfactory IR, 1H NMR, 13C NMR, ESI-MS spectra were obtained for all compounds described.
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- E.J. Yu, Y. Lee, S.Y. Rha, T.S. Kim, H.C. Chung, B.K. Oh, W.I. Yang, S.H. Noh and H.-C. Jeung, Mol. Cancer Res., 6, 1554 (2008); doi:10.1158/1541-7786.MCR-08-0166.
- A. Ishii, T. Kotani, Y. Nagaki, Y. Shibayama, Y. Toyomaki, N. Okukado, K. Ienaga and K. Okamoto, J. Med. Chem., 39, 1924 (1996); doi:10.1021/jm9508393.
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- C. Gaina, V. Gaina and V. Cozan, Eur. Polym. J., 37, 79 (2001); doi:10.1016/S0014-3057(00)00075-6.
- (a) N.S. Gandhi and R.L. Mancera, Chem. Biol. Drug Des., 72, 455 (2008); doi:10.1111/j.1747-0285.2008.00741.x; (b) M.G. Paulick and C.R. Bertozzi, Biochemistry, 47, 6991 (2008); doi:10.1021/bi8006324; (c) L.-X. Wang and W. Huang, Curr. Opin. Chem. Biol., 13, 592 (2009); doi:10.1016/j.cbpa.2009.08.014; (d) C.E. Bryant, D.R. Spring, M. Gangloff and N.J. Gay, Nat. Rev. Microbiol., 8, 8 (2010); doi:10.1038/nrmicro2266; (e) S. Taube, M. Jiang and C.E. Wobus, Viruses, 2, 1011 (2010); doi:10.3390/v2041011; (f) L. Liu, C.S. Bennett and C.H. Wong, Chem. Commun., 21, (2006); doi:10.1039/B513165K.
- C. Tao, F. Liu, W. Liu, Y. Zhu, Y. Li, X. Liu and J. Zhao, Tetrahedron Lett., 53, 7093 (2012); doi:10.1016/j.tetlet.2012.10.069.
- (a) W.W. Liu, Y.Q. Zhao, Y.Q. Pu, R.B. Xu and H.W. Hu, Chin. J. Org. Chem., 25, 838 (2005); (b) W.W. Liu, Y.Q. Zhao, R.B. Xu, L.J. Tang and H.W. Hu, Chin. J. Chem., 24, 1472 (2006); doi:10.1002/cjoc.200690278; (c) W.W. Liu, L.J. Tang, Y.X. Zeng, L. Wang, Y.Q. Zhao, K.Q. Chen and Z.E. Lu, Chin. J. Org. Chem., 27, 1285 (2007); (d) W. Liu, Y. Zhao, S. Tu, T. He and H. Hu, J. Heterocycl. Chem., 45, 1311 (2008); doi:10.1002/jhet.5570450509; (e) W.W. Liu, C.Z. Tao, L.J. Tang, J. Li, Y. Jin, Y.Q. Zhao and H.W. Hu, J. Heterocycl. Chem., 48, 361 (2011); doi:10.1002/jhet.585.
- (a) Ó. López, S. Maza, I. Maya, J. Fuentes and J.G. Fernández-Bolaños, Tetrahedron, 61, 9058 (2005); doi:10.1016/j.tet.2005.07.041; (b) Ó. López, E. Zafra, I. Maya, J. Fuentes, M.J. Diánez, M.D. Estrada, S. Pérez-Garrido and J.G. Fernández-Bolaños, Tetrahedron, 64, 11789 (2008); doi:10.1016/j.tet.2008.09.093; (c) O. López, S. Maza, V. Ulgar, I. Maya and J.G. Fernández-Bolaños, Tetrahedron, 65, 2556 (2009); doi:10.1016/j.tet.2009.01.038; (d) I. Maya, Ó. López, S. Maza, J.G. Fernández-Bolaños and J. Fuentes, Tetrahedron Lett., 44, 8539 (2003); doi:10.1016/j.tetlet.2003.09.140; (e) P.F. Wdey, D.L. McMichael, J.M. Koert and V.H. Wiley, J. Antibiotics, 29, 1218 (1976); doi:10.7164/antibiotics.29.1218; (f) J.C. Jochims and A. Seeliger, Tetrahedron, 21, 2611 (1965); doi:10.1016/S0040-4020(01)93917-1.
- H. Ulrich and A.A.R. Sayigh, J. Org. Chem., 30, 2781 (1965); doi:10.1021/jo01019a067.
References
E.J. Yu, Y. Lee, S.Y. Rha, T.S. Kim, H.C. Chung, B.K. Oh, W.I. Yang, S.H. Noh and H.-C. Jeung, Mol. Cancer Res., 6, 1554 (2008); doi:10.1158/1541-7786.MCR-08-0166.
A. Ishii, T. Kotani, Y. Nagaki, Y. Shibayama, Y. Toyomaki, N. Okukado, K. Ienaga and K. Okamoto, J. Med. Chem., 39, 1924 (1996); doi:10.1021/jm9508393.
M. Rajabi, D. Mansell, S. Freeman and R.A. Bryce, Eur. J. Med. Chem., 46, 1165 (2011); doi:10.1016/j.ejmech.2011.01.035.
C. Gaina, V. Gaina and V. Cozan, Eur. Polym. J., 37, 79 (2001); doi:10.1016/S0014-3057(00)00075-6.
(a) N.S. Gandhi and R.L. Mancera, Chem. Biol. Drug Des., 72, 455 (2008); doi:10.1111/j.1747-0285.2008.00741.x; (b) M.G. Paulick and C.R. Bertozzi, Biochemistry, 47, 6991 (2008); doi:10.1021/bi8006324; (c) L.-X. Wang and W. Huang, Curr. Opin. Chem. Biol., 13, 592 (2009); doi:10.1016/j.cbpa.2009.08.014; (d) C.E. Bryant, D.R. Spring, M. Gangloff and N.J. Gay, Nat. Rev. Microbiol., 8, 8 (2010); doi:10.1038/nrmicro2266; (e) S. Taube, M. Jiang and C.E. Wobus, Viruses, 2, 1011 (2010); doi:10.3390/v2041011; (f) L. Liu, C.S. Bennett and C.H. Wong, Chem. Commun., 21, (2006); doi:10.1039/B513165K.
C. Tao, F. Liu, W. Liu, Y. Zhu, Y. Li, X. Liu and J. Zhao, Tetrahedron Lett., 53, 7093 (2012); doi:10.1016/j.tetlet.2012.10.069.
(a) W.W. Liu, Y.Q. Zhao, Y.Q. Pu, R.B. Xu and H.W. Hu, Chin. J. Org. Chem., 25, 838 (2005); (b) W.W. Liu, Y.Q. Zhao, R.B. Xu, L.J. Tang and H.W. Hu, Chin. J. Chem., 24, 1472 (2006); doi:10.1002/cjoc.200690278; (c) W.W. Liu, L.J. Tang, Y.X. Zeng, L. Wang, Y.Q. Zhao, K.Q. Chen and Z.E. Lu, Chin. J. Org. Chem., 27, 1285 (2007); (d) W. Liu, Y. Zhao, S. Tu, T. He and H. Hu, J. Heterocycl. Chem., 45, 1311 (2008); doi:10.1002/jhet.5570450509; (e) W.W. Liu, C.Z. Tao, L.J. Tang, J. Li, Y. Jin, Y.Q. Zhao and H.W. Hu, J. Heterocycl. Chem., 48, 361 (2011); doi:10.1002/jhet.585.
(a) Ó. López, S. Maza, I. Maya, J. Fuentes and J.G. Fernández-Bolaños, Tetrahedron, 61, 9058 (2005); doi:10.1016/j.tet.2005.07.041; (b) Ó. López, E. Zafra, I. Maya, J. Fuentes, M.J. Diánez, M.D. Estrada, S. Pérez-Garrido and J.G. Fernández-Bolaños, Tetrahedron, 64, 11789 (2008); doi:10.1016/j.tet.2008.09.093; (c) O. López, S. Maza, V. Ulgar, I. Maya and J.G. Fernández-Bolaños, Tetrahedron, 65, 2556 (2009); doi:10.1016/j.tet.2009.01.038; (d) I. Maya, Ó. López, S. Maza, J.G. Fernández-Bolaños and J. Fuentes, Tetrahedron Lett., 44, 8539 (2003); doi:10.1016/j.tetlet.2003.09.140; (e) P.F. Wdey, D.L. McMichael, J.M. Koert and V.H. Wiley, J. Antibiotics, 29, 1218 (1976); doi:10.7164/antibiotics.29.1218; (f) J.C. Jochims and A. Seeliger, Tetrahedron, 21, 2611 (1965); doi:10.1016/S0040-4020(01)93917-1.
H. Ulrich and A.A.R. Sayigh, J. Org. Chem., 30, 2781 (1965); doi:10.1021/jo01019a067.