Synthesis and evaluation of debromohymenialdisine-derived Chk2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 4, 2012, Pages 1475-1481

  Saleem, Rahman Shah Zaib ^a   Lansdell, Theresa A ^a   Tepe, Jetze J ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Checkpoint kinases; Chk2; Debromohymenialdisine; Hymenialdisine; Natural products; Radioprotection

Indexed keywords

12 (2 CYANOETHYL) 6,7,12,13 TETRAHYDRO 13 METHYL 5 OXOINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE; 2 (3,4 DIMETHOXYPHENYL) 4 (2 (METHYLTHIO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 2 (3,4 DIMETHOXYPHENYL) 6,7 DIHYDROPYRROLO [2,3 C]AZEPINE 4,8 (1H,5H)DIONE; 2 (4 METHOXYPHENYL) 4 (2 (METHYLTHIO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 2 (4 METHOXYPHENYL) 6,7 DIHYDROPYRROLO [2,3 C]AZEPINE 4,8 (1H,5H)DIONE; 2 PHENYL 6,7 DIHYDROPYRROLO [2,3 C]AZEPINE 4,8 (1H,5H)DIONE; 4 (2 (BENZYLAMINO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 (CYCLOHEXYLAMINO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 (METHOXYBENZYLAMINO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 (METHYLAMINO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 (METHYLTHIO) 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 AMINO 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 (4 METHOXYPHENYL) 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 AMINO 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (2 AMINO 4 OXO 1H IMIDAZOL 5 (4H) YLIDENE) 3 (4 DIMETHOXYPHENYL) 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 4 (4 OXO 2 (PROPYLAMINO) 1H IMIDAZOL 5 (4H) YLIDENE) 2 PHENYL 4,5,6,7 TETRAHYDROPYRROLO [2,3 C]AZEPIN 8 (1H) ONE; 7 HYDROXYSTAUROSPORINE; ARYL BENZIMIDAZOLE; CCT 241533; CHECKPOINT KINASE 1; CHECKPOINT KINASE 2; DEBROMOHYMENIALDISINE; ENZYME INHIBITOR; ETHYL 3 ((4 OXO 5 (8 OXO 2 PHENYL 5,6,7,8 TETRABHYDROPYRROLO [2,3 C]AZEPIN 4 (1H) YLIDENE) 4,5 DIHYDRO 1H IMIDAZOL 2 YL)AMINO)PROPANOIC ACID; INDOLEAZEPINE; NATURAL PRODUCT; NSC 109555; PV 1019; UNCLASSIFIED DRUG; VRX 0466617;

ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME DEGRADATION; ENZYME INHIBITION; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; RADIATION PROTECTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; AZEPINES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; ENZYME ACTIVATION; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PORIFERA; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; PROTEIN-SERINE-THREONINE KINASES; PYRROLES; SUBSTRATE SPECIFICITY;

EID: 84857032650     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.12.054     Document Type: Article

References (32)

1. J. Smith, L.M. Tho, N. Xu, and D.A. Gillespie Adv. Cancer Res. 108 2010 73
2. J. Kao, B.S. Rosenstein, S. Peters, M.T. Milano, and S.J. Kron NY Ann. Acad. Sci. 1066 2006 243
3. R.T. Abraham Genes Dev. 15 2001 2177
4. L. Zou, and S.J. Elledge Science 300 2003 1542
5. J.H. Lee, and T.T. Paull Science 308 2005 551
6. J. Bartek, and J. Lukas Cancer Cell 3 2003 421
7. B.S. Zhou, and J. Bartek Nat. Rev. Cancer 4 2004 216
8. J. Bartkova, Z. Horejsi, K. Koed, A. Kramer, F. Tort, K. Zieger, P. Guldberg, M. Sehested, J.M. Nesland, C. Lukas, T. Orntoft, J. Lukas, and J. Bartek Nature 434 2005 864
9. T.N. Nguyen, and J.J. Tepe Curr. Med. Chem. 16 2009 3122
10. Y. Pommier, J.N. Weinstein, M.I. Aladjem, and K.W. Kohn Clin. Cancer. Res. 12 2006 2657
11. G. Zoppoli, S. Solier, W.C. Reinhold, H. Liu, J.W. Connelly Jr., A. Monks, R.H. Shoemaker, O.D. Abaan, S.R. Davis, P.S. Meltzer, J.H. Doroshow, and Y. Pommier Oncogene 2011 1
12. A.G. Jobson, G.T. Lountos, P.L. Lorenzi, J. Llamas, J. Connelly, D. Cerna, J.E. Tropea, A. Onda, G. Zoppoli, S. Kondapaka, G. Zhang, N.J. Caplen, J.H. Cardellina 2nd, S.S. Yoo, A. Monks, C. Self, D.S. Waugh, R.H. Shoemaker, and Y.J. Pommier Pharmacol. Exp. Ther. 331 2009 816
13. T.N. Nguyen, R.S. Saleem, M.J. Luderer, S. Hovde, R.W. Henry, and J.J. Tepe ACS Chem. Biol. 2011 doi: 10.1021/cb200320c
14. H. Takai, K. Naka, Y. Okada, M. Watanabe, N. Harada, S. Saito, C.W. Anderson, E. Appella, M. Nakanishi, H. Suzuki, K. Nagashima, H. Sawa, K. Ikeda, and N. Motoyama EMBO J. 21 2002 5195
15. Q. Yu, J. La Rose, H. Zhang, H. Takemura, K.W. Kohn, and Y. Pommier Cancer Res. 62 2002 5743
16. E.A. Kohn, C.J. Yoo, and A. Eastman Cancer Res. 63 2003 31
17. D.J. Matthews, F.M. Yakes, J. Chen, M. Tadano, L. Bornheim, D.O. Clary, A. Tai, J.M. Wagner, N. Miller, Y.D. Kim, S. Robertson, L. Murray, and L.M. Karnitz Cell Cycle 6 2007 104
18. G.T. Lountos, J.E. Tropea, D. Zhang, A.G. Jobson, Y. Pommier, R.H. Shoemaker, and D.S. Waugh Protein Sci. 18 2009 92
19. A.G. Jobson, J.H. Cardellina 2nd, D. Scudiero, S. Kondapaka, H. Zhang, H. Kim, R. Shoemaker, and Y. Pommier Mol. Pharmacol. 72 2007 876
20. L. Carlessi, G. Buscemi, G. Larson, Z. Hong, J.Z. Wu, and D. Delia Mol. Cancer Ther. 6 2007 935
21. V.E. Anderson, M.I. Walton, P.D. Eve, K.J. Boxall, L. Antoni, J.J. Caldwell, W. Aherne, L.H. Pearl, A.W. Oliver, I. Collins, and M.D. Garrett Cancer Res. 71 2011 463
22. J.J. Caldwell, E.J. Welsh, C. Matijssen, V.E. Anderson, L. Antoni, K. Boxall, F. Urban, A. Hayes, F.I. Raynaud, L.J. Rigoreau, T. Raynham, G.W. Aherne, L.H. Pearl, A.W. Oliver, M.D. Garrett, and I. Collins J. Med. Chem. 54 2011 580
23. S. Hilton, S. Naud, J.J. Caldwell, K. Boxall, S. Burns, V.E. Anderson, L. Antoni, C.E. Allen, L.H. Pearl, A.W. Oliver, G. Wynne Aherne, M.D. Garrett, and I. Collins Bioorg. Med. Chem. 18 2010 707
24. K.L. Arienti, A. Brunmark, F.U. Axe, K. McClure, A. Lee, J. Blevitt, D.K. Neff, L. Huang, S. Crawford, C.R. Pandit, L. Karlsson, and J.G. Breitenbucher J. Med. Chem. 48 2005 1873
25. K.J. McClure, L. Huang, K.L. Arienti, F.U. Axe, A. Brunmark, J. Blevitt, and J.G. Breitenbucher Bioorg. Med. Chem. Lett. 16 2006 1924
26. D.K. Neff, A. Lee-Dutra, J.M. Blevitt, F.U. Axe, M.D. Hack, J.C. Buma, R. Rynberg, A. Brunmark, L. Karlsson, and J.G. Breitenbucher Bioorg. Med. Chem. Lett. 17 2007 6467
27. V. Sharma, and J.J. Tepe Bioorg. Med. Chem. Let. 14 2004 4319
28. D. Tasdemir, R. Mallon, M. Greenstein, L.R. Feldberg, S.C. Kim, K. Collins, D. Wojciechowicz, G.C. Mangalindan, G.P. Concepcion, M.K. Harper, and C.M. Ireland J. Med. Chem. 45 2002 529
29. D. Curman, B. Cinel, D.E. Williams, N. Rundle, W.D. Block, A.A. Goodarzi, J.R. Hutchins, P.R. Clarke, B.B. Zhou, S.P. Lees-Miller, R.J. Andersen, and M. Roberge J. Biol. Chem. 276 2001 17914
30. L. Meijer, A.M. Thunnissen, A.W. White, M. Garnier, M. Nikolic, L.H. Tsai, J. Walter, K.E. Cleverley, P.C. Salinas, Y.Z. Wu, J. Biernat, E.M. Mandelkow, S.H. Kim, and G.R. Pettit Chem. Biol. 7 2000 51
31. A.W. Oliver, A. Paul, K.J. Boxall, S.E. Barrie, G.W. Aherne, M.D. Garrett, S. Mittnacht, and L.H. Pearl EMBO J. 25 2006 3179
32. H. Annoura, and T. Tatsuoka Tetrahedron Lett. 36 1995 413