Bis-imide granulatimide analogues as potent Checkpoint 1 kinase inhibitors

Anderson, 2003, Inhibitors of the G2 DNA damage checkpoint and their potential for cancer therapy, vol. 5, 423 Berlinck, 1998, Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum: structure elucidation and synthesis, J. Org. Chem., 63, 9850, 10.1021/jo981607p Chen, 2000, The 1.7? crystal structure of human cell cycle checkpoint kinase Chk1: implications for Chk1 regulation, Cell, 100, 681, 10.1016/S0092-8674(00)80704-7 Davies, 2000, Specificity and mechanism of action of some commonly used protein kinase inhibitors, Biochem. J., 351, 95, 10.1042/0264-6021:3510095 Gray, 1999, ATP-site directed inhibitors of cyclin-dependent kinases, Curr. Med. Chem., 6, 859, 10.2174/092986730609220401152358 Hénon, 2005, Synthesis of granulatimide bis-imide analogues, Tetrahedron, 61, 5599, 10.1016/j.tet.2005.03.101 Hénon, 2006, Synthesis of dipyrrolo[3,4-a;3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety, Tetrahedron, 62, 1116, 10.1016/j.tet.2005.10.077 Hénon, 2006, Expedited synthesis of substituted dipyrrolo[3,4-a;3,4-c]carbazole-1,3,4,6-tetraones structurally related to granulatimide, Synthesis, 711 Hénon, 2006, Synthesis and biological evaluation of new dipyrrolo[3,4-a;3,4-c]carbazole-1,3,4,6-tetraones substituted with various saturated and unsaturated side chains via palladium catalysed cross-coupling reactions, Bioorg. Med. Chem., 14, 3825, 10.1016/j.bmc.2006.01.030 Hugon, 2003, Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle, Tetrahedron Lett., 44, 3927, 10.1016/S0040-4039(03)00837-2 Hugon, 2003, Synthesis of granulatimide analogues bearing a maleimide instead of an imidazole heterocycle, Tetrahedron Lett., 44, 3935, 10.1016/S0040-4039(03)00823-2 Hugon, 2003, Synthesis of isogranulatimides A and B analogues possessing a 7-azaindole unit instead of an indole moiety, Tetrahedron Lett., 44, 4607, 10.1016/S0040-4039(03)00924-9 Jiang, 2004, Inhibition of Chk1 by the G2 DNA damage checkpoint inhibitor isogranulatimide, Mol. Cancer Ther., 3, 1221, 10.1158/1535-7163.1221.3.10 Léonce, 1996, In vitro cytotoxicity of S16020-2, a new olivacine derivative, Invest. New Drugs, 14, 169, 10.1007/BF00210788 Luo, 2001, Blocking Chk1 expression induces apoptosis and abrogates the G2 checkpoint mechanism, Neoplasia, 3, 411, 10.1038/sj.neo.7900175 Molinari, 2000, Cell cycle checkpoints and their inactivation in human cancer, Cell Prolif., 33, 261, 10.1046/j.1365-2184.2000.00191.x Piers, 2000, Improved synthesis of isogranulatimide, a G2 checkpoint inhibitor. Syntheses of didemnimide C, isodidemnimide A, neodidemnimide A, 17-methylgranulatimide, and isogranulatimides A–C, J. Org. Chem., 65, 530, 10.1021/jo9914723 Prudhomme, 2004, Combining DNA damaging agents and Chk1 inhibitors, Curr. Med. Chem.-Anti-Cancer Agents, 4, 435, 10.2174/1568011043352795 Prudhomme, M., 2006. Novel Chk1 inhibitors. Recent Patents on Anti-Cancer Drug Discovery, 1, 55-68. Roberge, 1998, High-throughput assay for G2 checkpoint inhibitors and identification of the structurally novel compound isogranulatimide, Cancer Res., 58, 5701 Suganuma, 1999, Sensitization of cancer cells to DNA damage-induced cell death by specific cell cycle G2 checkpoint abrogation, Cancer Res., 59, 5887 Tao, 2006, Chk1 inhibitors for novel cancer treatment, Anti-Cancer Agents Med. Chem., 6, 377, 10.2174/187152006777698132 Walworth, 1993, Fission yeast chk1 protein kinase links the rad checkpoint pathway to cdc2, Nature, 363, 368, 10.1038/363368a0 Wang, L., Liu, X., Chen, R., 2003. Derivatives of isoindigo, indigo and indirubin and use in treating cancer, International patent WO03051900, CA 139:47135. Yoshida, 2002, New synthetic route to granulatimide and its structural analogues, Chem. Pharm. Bull., 50, 872, 10.1248/cpb.50.872 Yoshida, 2003, Synthesis of granulatimide positional analogues, Chem. Pharm. Bull., 51, 209, 10.1248/cpb.51.209 Zhao, 2002, Structural basis for Chk1 inhibition by UCN-01, J. Biol. Chem., 277, 46609, 10.1074/jbc.M201233200 Zhou, 2000, The DNA damage response: putting checkpoints in perspective, Nature, 408, 433, 10.1038/35044005