Synthesis and biological activities of new checkpoint kinase 1 inhibitors structurally related to granulatimide

Journal of Medicinal Chemistry

Volumn 50, Issue 19, 2007, Pages 4669-4680

  Conchon, Elisabeth ^a   Anizon, Fabrice ^a   Aboab, Bettina ^a   Prudhomme, Michelle ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

11 HYDROXYBENZO[A]PYRROLO[3,4 C]CARBAZOLE 1,3,4,7(2H,8H) TETRAONE; 4,11 TRIHYDROXYBENZO[A]PYRROLO[3,4 C]CARBAZOLE 1,3(2H,8H) DIONE; CARBAZOLE DERIVATIVE; CHECKPOINT KINASE 1; ENZYME INHIBITOR; GRANULATIMIDE; HYDROQUINONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HCT116; CELL STRAIN HT29; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA L 1210; MOLECULAR MODEL; MOUSE; NONHUMAN;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; CARBAZOLES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34648816236     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070664k     Document Type: Article

References (48)

1. Roberge, M.; Berlinck, R. G. S.; Xu, L.; Anderson, H. J.; Lim, L. Y.; Curman, D.; Stringer, C. M.; Friend, S. H.; Davies, P.; Vincent, I.; Haggarty, S. J.; Kelly, M. T.; Britton, R.; Piers, E.; Andersen, R. J. High-throughput assay for G2 checkpoint inhibitors and identification of the structurally novel compound isogranulatimide. Cancer Res. 1998, 58, 5701-5706.
2. Berlinck, R. G. S.; Britton, R.; Piers, E.; Lim, L.; Roberge, M.; Moreira da Rocha, R.; Andersen, R. J. Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the brazilian ascidian Didemnum granulatum; Structure elucidation and synthesis. J. Org. Chem. 1998, 63, 9850-9856.
3. Anderson, H. J.; Andersen, R. J.; Roberge, M. Inhibitors of the G2 DNA damage checkpoint and their potential for cancer therapy. Progress in the Cell Cycle Research: Meijer, L., Jézéquel, A., Roberge, M., Eds.; Kluwer Acedemic: Dordrecht, The Netherlands, 2003; Vol. 5, pp 423-430.
4. Jiang, X.; Zhao, B.; Britton, R.; Lim, L. Y.; Leong, D.; Sanghera, J. S.; Zhou, B.-B. S.; Piers, E.; Andersen, R. J.; Roberge, M. Inhibition of Chk1 by the G2 DNA damage checkpoint inhibitor isogranulatimide. Mol. Cancer Ther. 2004, 3, 1221-1227.
5. Chène, P. Targeting p53 in Cancer. Curr. Med. Chem.-Anti-Cancer Agents 2001, 1, 151-161.
6. Luo, Y.; Rockow-Magnone, S. K.; Kroeger, P. A.; Frost, L.; Chen, Z.; Han, E. K.-H.; Ng, S.-C.; Simmer, R. L.; Giranda, V. L. Blocking Chk1 expression induces apoptosis and abrogates the G2 checkpoint mechanism. Neoplasia 2001, 3, 411-419.
7. Hartwell, L.; Kastan, M. B. Cell cycle control and cancer. Science 1994, 266, 1821-1828.
8. Shapiro, I. G.; Harper, J. W. Anticancer drug targets: Cell cycle and checkpoint control. J. Clin. Invest. 1999, 104, 1645-1653.
9. Zhou, B. B. S.; Elledge, S. J. The DNA damage response: Putting checkpoints in perspective. Nature 2000, 408, 433-439.
10. Prudhomme, M. Combining DNA damaging agents and checkpoint 1 inhibitors. Curr. Med. Chem. - Anti-Cancer Agents 2004, 4, 435-438.
11. Chen, Z.; Xiao, Z.; Gu, W.; Xue, J.; Bui, M. H.; Kovar, P.; Li, G.; Wang, G.; Tao, Z.-F.; Tong, Y.; Lin, N.-H.; Sham, H. L.; Wang, J. Y. J.; Sowin, T. J.; Rosenberg, S. H.; Zhang, H. Selective Chk1 inhibitors differentially sensitize p-53 deficient cancer cells to cancer therapeutics. Int. J. Cancer 2006, 119, 2784-2794.
12. Bartek, J.; Lukas, J. Chk1 and Chk2 kinases in checkpoint control and cancer. Cancer Cell 2003, 3, 421-429.
13. Sancar, A.; Lindsey-Boltz, L. A.; Unsal-Kaçmaz, K.; Linn, S. Molecular mechanisms of mammalian DNA repair and the DNA damage checkpoints. Ann. Rev. Biochem. 2004, 73, 39-85.
14. Kawabe, T. G2 checkpoint abrogators as anticancer drags. Mol. Cancer Ther. 2004, 513-519.
15. a) Le Gac, G.; Estève, P.-O.; Ferec, C.; Pradhan, S. DNA damage-induced down-regulation of human Cdc25c and Cdc2 is mediated by cooperation between p53 and maintenance DNA (cytosine-5) methyltransferase 1. J. Biol. Chem. 2006, 281, 24161-24170.
16. b) Rudolph, J. Cdc25 phosphatases: structure, specificity, and mechanism. Biochemistry 2007, 46, 3595-3604.
17. Hotte, S. J.; Oza, A.; Winquist, E. W.; Moore, M.; Chen, E. X.; Brown, S.; Pond, G. R.; Dancey, J. E.; Hirte, H. W. Phase I trial of UCN-01 in combination with topotecan in patients with advanced solid cancers: A Princess Margaret Hospital Phase II Consortium study. Ann. Oncol. 2006, 17, 334-40.
18. Kortmansky, J.; Shah, M. A.; Kaubisch, A.; Weyerbacher, A.; Yi, S.; Tong, W.; Sowers, R.; Gonen, M.; O'reilly, E.; Kemeny, N.; Ilson, D. I.; Saltz, L. B.; Maki, R. G.; Kelsen, D. P.; Schwartz, G. K. Phase I trial of the cyclin-dependent kinase inhibitor and protein kinase C inhibitor 7-hydroxystaurosporine in combination with Fluorouracil in patients with advanced solid tumors. J. Clin. Oncol. 2005, 23, 1875-84.
19. Zhao, B.; Bower, M. J.; McDevitt, P. J.; Zhao, H.; Davis, S. T.; Johanson, K. O.; Green, S. M.; Concha, N. O.; Zhou, B. B. S. Structural basis for Chk1 inhibition by UCN-01. J. Biol. Chem. 2002, 277, 46609-46615.
20. Piers, E.; Britton, R.; Andersen, R. J. 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. 2000, 65, 530-535.
21. Yoshida, T.; Nishiyachi, M.; Nakashima, N.; Murase, M.; Kotani, E. New synthetic route to granulatimide and its structural analogues. Chem. Pharm. Bull. 2002, 50, 872-876.
22. Yoshida, T.; Nishiyachi, M.; Nakashima, N.; Murase, M.; Kotani, E. Synthesis of granulatimide positional analogues. Chem. Pharm. Bull. 2003, 51, 209-214.
23. Terpin, A.; Winklhofer, C.; Schumann, S.; Steglich, W. Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer. Tetrahedron 1998, 54, 1745-1752.
24. Hugon, B.; Pfeiffer, B.; Renard, P.; Prudhomme, M. Synthesis of isogranulatimide analogues possessing a pyrrole moiety instead of an imidazole heterocycle. Tetrahedron Lett. 2003, 44, 3927-3930.
25. Hugon, B.; Pfeiffer, B.; Renard, P.; Prudhomme, M. Synthesis of isogranulatimides A and B analogues possessing a 7-azaindole unit instead of an indole moiety. Tetrahedron Lett. 2003, 44, 4607-4611.
26. Hugon, B.; Pfeiffer, B.; Renard, P.; Prudhomme, M. Synthesis of granulatimide analogues bearing a maleimide instead of an imidazole heterocycle. Tetrahedron Lett. 2003, 44, 3935-3937.
27. Hénon, H.; Messaoudi, S.; Hugon, B.; Anizon, F.; Pfeiffer, B.; Prudhomme, M. Synthesis of granulatimide bis-imide analogues. Tetrahedron 2005, 61, 5599-5614.
28. Hénon, H.; Anizon, F.; Kucharczyk, N.; Loynel, A.; Casara, P.; Pfeiffer, B.; Prudhomme, M. Expedited synthesis of substituted dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones structurally related to granulatimide. Synthesis 2006, 4, 711-715.
29. Hénon, H.; Anizon, F.; Golsteyn, R. M.; Léonce, S.; Hofmann, R.; Pfeiffer, B.; Prudhomme, M. 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 cross-coupling reactions. Bioorg. Med. Chem. 2006, 14, 3825-3834.
30. Hénon, H.; Messaoudi, M.; Anizon, F.; Aboab, B.; Kucharczyk, N.; Léonce, S.; Golsteyn, R. M.; Pfeiffer, B.; Prudhomme, M. Bis-imide granulatimide analogues as potent Checkpoint 1 kinase inhibitors. Eur. J. Pharmacol. 2007, 554, 106-112.
31. Bergman, J.; Desarbre, E.; Koch, E. Synthesis of indolo[3,2-a] pyrrolo-[3,4-c]carbazole in one step from indole and maleimide. Tetrahedron 1999, 55, 2363-2370.
32. Bergman, J.; Janosik, T.; Koch, E.; Pelcman, B. Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives. J. Chem. Soc. Perkin Trans. 1 2000, 2615-2621.
33. 1H NMR spectra of indoline and indole in DMSO. The chemical shifts of the NH protons of indoline and indole in DMSO are 5.42 and 11.06 ppm, respectively.
34. Vazquez, E.; Davies, I. W.; Payack, J. F. A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols J. Org. Chem. 2002, 67, 7551-7552.
35. Sutherland, A.; Gallagher, T. Versatile synthesis of 3,5-disubstituted 2-fluoropyridines and 3-pyridones. J. Org. Chem. 2003, 68, 3352-3355.
36. de Koning, B. C.; Michael, J. P.; Rousseau, A. L. A versatile and convenient method for the synthesis of substituted benzo[a]carbazoles and pyrido[2,3-a]carbazoles. J. Chem. Soc. Perkin Trans. 1, 2000, 1705-1713.
37. D'Alessio, R.; Bargiotti, A.; Carlini, O.; Colotta, F.; Ferrari, M.; Gnocchi, P.; Isetta, A.; Mongelli, N.; Motta, P.; Rossi, A.; Rossi, M.; Tibolla, M.; Vanotti, E. Synthesis and immunosuppressive activity of novel prodigiosin derivatives. J. Med. Chem. 2000, 43, 2557-2565.
38. Marson, C. M.; Farrand, L. D.; Brettle, R.; Dunmur, D. A. Highly efficient syntheses of 3-aryl-2-cycloalken-1-ones and evaluation of their liquid crystalline properties. Tetrahedron 2003, 19, 4377-4381.
39. Shih, C.; Swenton, J. S. Use of protected β-bromocyclopentenones and β-bromocyclohexenones as β-acylvinyl anion equivalent. J. Org. Chem. 1982, 47, 2825-2832.
40. Clive, D. L. J.; Fletcher, S. P.; Liu, D. Formal radical cyclization onto benzene rings: A general method and its use in the synthesis of ent-nocardione A. J. Org. Chem. 2004, 69, 3282-3293.
41. Amari, G.; Armani, E.; Ghirardi, S.; Delcanale, M.; Civelli, M.; Caruso, P. L.; Galbiati, E.; Lipreri, M.; Rivara, S.; Lodola, A.; Mor, M. Synthesis, pharmacological evaluation, and structure-activity relationships of benzopyran derivatives with potent SERM activity. Bioorg. Med. Chem. 2004, 12, 3763-3782.
42. Brown, R. J.; Annis, G.; Casalnuovo, A.; Chan, D.; Shapiro, R.; Marshall, W. J. Synthesis and properties of axially-chiral N-(2,6-disubstituted) phenyl triazolones. Tetrahedron 2004, 60, 4361-4375.
43. Palmer, B. D.; Thompson, A. M.; Booth, R. J.; Dobrusin, E. M.; Kraker, A. J.; Lee, H. H.; Lunney, E. A.; Mitchell, L. H.; Ortwine, D. F.; Smaill, J. B.; Swan, L. M.; Denny, W. A. 4-Phenylpyrrolo-[3,4-c]carbazole-1,3(2H, 6H)-dione inhibitors of the checkpoint kinase Weel. Structure-activity relationships for chromophore modification and phenyl ring substitution. J. Med. Chem. 2006, 49, 4896-4911.
44. Macromodel 8.0: Shroedinger Inc, 1500 SW First Ave. Suite 1180, Portland, OR 97201.
45. Weiner, S. J.; Kollman, P. A.; Case, A. D.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner, P. A new force field for molecular mechanical simulation of nucleic acids and proteins. J. Am. Chem. Soc. 1984, 106, 765-784.
46. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. M.; Kollman, P. A. A Second Generation Force Field for the Simulation of Proteins, Nucleic Acids, and Organic Molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
47. Davies, S. P.; Reddy, H.; Caivano, M.; Cohen, P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem. J. 2000, 351, 95-105.
48. Léonce, S.; Pérez, V.; Casabianca-Pignède, M. R.; Anstett, M.; Bisagni, E.; Atassi, G. In vitro cytotoxicity of S16020-2, a new olivacine derivative. Invest. New Drugs 1996, 14, 169-180.