Discovery of 1-substituted benzyl-quinazoline-2,4(1H,3H)-dione derivatives as novel poly(ADP-ribose)polymerase-1 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 4, 2015, Pages 681-693

  Yao, Haiping ^a   Ji, Ming ^a   Zhu, Zhixiang ^a   Zhou, Jie ^a   Cao, Ran ^a   Chen, Xiaoguang ^a   Xu, Bailing ^a  

^a PEKING UNION MEDICAL COLLEGE   (China)

Author keywords

Antitumor activity; PARP 1 inhibitor; PARP 2 inhibitor; Quinazoline 2 4(1H 3H) dione

Indexed keywords

2 (DIMETHYLAMINO) N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]ACETAMIDE; 2 AMINO N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] 3 METHYL BUTANAMIDE 2,2,2 TRIFLUOROACETIC ACID; 2 AMINO N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]ACETAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] 2 (METHYLAMINO)ACETAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]PIPERIDINE 3 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]PYRROLIDINE 2 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]PYRROLIDINE 3 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]PIPERIDINE 3 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]PYRROLIDINE 2 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]PYRROLIDINE 3 CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; N [5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]PYRROLIDINE CARBOXAMIDE 2,2,2 TRIFLUOROACETIC ACID; PHOSPHATIDYLINOSITOL 3,4,5 TRISPHOSPHATE 3 PHOSPHATASE; QUINAZOLINE DERIVATIVE; TEMOZOLOMIDE; TERT BUTYL 2 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]CARBAMOYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [[5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]CARBAMOYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [[5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 3 [[5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]CARBAMOYL]PYRROLIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[2 FLUORO 5 [(5 FLUORO 2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[2 FLUORO 5 [(6 FLUORO 2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[2 FLUORO 5 [(7 FLUORO 2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[2 FLUORO 5 [(8 FLUORO 2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL] CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL 4 [[5 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL] 2 FLUOROPHENYL]CARBAMOYL]PIPERIDINE 1 CARBOXYLIC ACID; TERT BUTYL [1 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]AMINO] 3 METHYL 1 OXOBUTAN 2 YL]CARBOXYLIC ACID; TERT BUTYL [2 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]AMINO] 2 OXOETHYL](METHYL)CARBOXYLIC ACID; TERT BUTYL [2 [[3 [(2,4 DIOXO 3,4 DIHYDROQUINAZOLIN 1(2H) YL)METHYL]PHENYL]AMINO] 2 OXOETHYL]CARBOXYLIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BREAST CANCER CELL LINE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC50; MDA MB 231 CELL LINE; MDA MB 468 CELL LINE; MX 1 CELL LINE; PTEN GENE; STRUCTURE ACTIVITY RELATION; TUMOR SUPPRESSOR GENE;

EID: 84964308855     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.12.071     Document Type: Article

References (52)

1. K. Do, and A.P. Chen Clin. Cancer Res. 19 2013 977
2. M. Rouleau, A. Patel, M.J. Hendzel, S.H. Kaufmann, and G.G. Poirier Nat. Rev. Cancer 10 2010 293
3. B.A. Gibson, and W.L. Kraus Nat. Rev. Mol. Cell Biol. 13 2012 411
4. M.F. Langelier, J.L. Planck, S. Roy, and J.M. Pascal Science 336 2012 728
5. M.F. Langelier, J.L. Planck, S. Roy, and J.M. Pascal J. Biol. Chem. 286 2011 10690
6. G. de Murcia, V. Schreiber, M. Molinete, B. Saulier, O. Poch, M. Masson, C. Niedergang, and J. Ménissier de Murcia Mol. Cell. Biochem. 138 1994 15
7. M.O. Hottiger, P.O. Hassa, B. Lüscher, H. Schüler, and F. Koch-Nolte Trends Biochem. Sci. 35 2010 208
8. J.P. Gagné, M. Isabelle, K.S. Lo, S. Bourassa, M.J. Hendzel, V.L. Dawson, T.M. Dawson, and G.G. Poirier Nucleic Acids Res. 36 2008 6959
9. M. De Vos, V. Schreiber, and F. Dantzer Biochem. Pharmacol. 84 2012 137
10. B.W. Durkacz, O. Omidiji, D.A. Gray, and S. Shall Nature 283 1980 593
11. M. Javle, and N.J. Curtin Br. J. Cancer 105 2011 1114
12. C.A. Delaney, L.Z. Wang, S. Kyle, A.W. White, A.H. Calvert, N.J. Curtin, B.W. Durkacz, Z. Hostomsky, and D.R. Newell Clin. Cancer Res. 6 2000 2860
13. R.A. Daniel, A.L. Rozanska, E.A. Mulligan, Y. Drew, H.D. Thomas, D.J. Castelbuono, Z. Hostomsky, E.R. Plummer, D.A. Tweddle, A.V. Boddy, S.C. Clifford, and N.J. Curtin Br. J. Cancer 103 2010 1588
14. S. Kummar, J. Ji, R. Morgan, H.J. Lenz, S.L. Puhalla, C.P. Belani, D.R. Gandara, D. Allen, B. Kiesel, J.H. Beumer, E.M. Newman, L. Rubinstein, A. Chen, Y. Zhang, L. Wang, R.J. Kinders, R.E. Parchment, J.E. Tomaszewski, and J.H. Doroshow Clin. Cancer Res. 18 2012 1726
15. B. Evers, R. Drost, E. Schut, M. de Bruin, E. van der Burg, P.W. Derksen, H. Holstege, X. Liu, E. van Drunen, H.B. Beverloo, G.C. Smith, N.M. Martin, A. Lau, M.J. O'Connor, and J. Jonkers Clin. Cancer Res. 14 2008 3916
16. C.K. Donawho, Y. Luo, Y. Luo, T.D. Penning, J.L. Bauch, J.J. Bouska, V.D. Bontcheva-Diaz, B.F. Cox, T.L. DeWeese, L.E. Dillehay, D.C. Ferguson, N.S. Ghoreishi-Haack, D.R. Grimm, R. Guan, E.K. Han, R.R. Holley-Shanks, B. Hristov, K.B. Idler, K. Jarvis, E.F. Johnson, L.R. Kleinberg, V. Klinghofer, L.M. Lasko, X. Liu, K.C. Marsh, T.P. McGonigal, J.A. Meulbroek, A.M. Olson, J.P. Palma, L.E. Rodriguez, Y. Shi, J.A. Stavropoulos, A.C. Tsurutani, G.D. Zhu, S.H. Rosenberg, V.L. Giranda, and D.J. Frost Clin. Cancer Res. 13 2007 2728
17. H. Farmer, N. McCabe, C.J. Lord, A.N. Tutt, D.A. Johnson, T.B. Richardson, M. Santarosa, K.J. Dillon, I. Hickson, C. Knights, N.M. Martin, S.P. Jackson, G.C. Smith, and A. Ashworth Nature 434 2005 917
18. H.E. Bryant, N. Schultz, H.D. Thomas, K.M. Parker, D. Flower, E. Lopez, S. Kyle, M. Meuth, N.J. Curtin, and T. Helleday Nature 434 2005 913
19. P.C. Fong, D.S. Boss, T.A. Yap, A. Tutt, P. Wu, M. Mergui-Roelvink, P. Mortimer, H. Swaisland, A. Lau, M.J. O'Connor, A. Ashworth, J. Carmichael, S.B. Kaye, J.H. Schellens, and J.S. de Bono N. Eng. J. Med. 361 2009 123
20. K.A. Mason, U. Raju, T.A. Buchholz, L. Wang, Z.L. Milas, and L. Milas Am. J. Clin. Oncol. 37 2014 90
21. J.F. Liu, P.A. Konstantinopoulos, and U.A. Matulonis Gynecol. Oncol. 133 2014 362
22. M.R. Purnell, and W.J. Whish Biochem. J. 185 1980 775
23. M.R. Patel, A. Bhatt, J.D. Steffen, A. Chergui, J. Murai, Y. Pommier, J.M. Pascal, L.D. Trombetta, F.R. Fronczek, and T.T. Talele J. Med. Chem. 57 2014 5579
24. N. Ye, C.H. Chen, T. Chen, Z. Song, J.X. He, X.J. Huan, S.S. Song, Q. Liu, Y. Chen, J. Ding, Y. Xu, Z.H. Miao, and A. Zhang J. Med. Chem. 56 2013 2885
25. G.D. Zhu, J. Gong, V.B. Gandhi, X. Liu, Y. Shi, E.F. Johnson, C.K. Donawho, P.A. Ellis, J.J. Bouska, D.J. Osterling, A.M. Olson, C. Park, Y. Luo, A. Shoemaker, V.L. Giranda, and T.D. Penning Bioorg. Med. Chem. 20 2012 4635
26. D.V. Ferraris J. Med. Chem. 53 2010 4561
27. K.A. Menear, C. Adcock, R. Boulter, X.L. Cockcroft, L. Copsey, A. Cranston, K.J. Dillon, J. Drzewiecki, S. Garman, S. Gomez, H. Javaid, F. Kerrigan, C. Knights, A. Lau, V.M. Loh Jr., I.T. Matthews, S. Moore, M.J. O'Connor, G.C. Smith, and N.M. Martin J. Med. Chem. 51 2008 6581
28. T.D. Penning, G.D. Zhu, V.B. Gandhi, J. Gong, X. Liu, Y. Shi, V. Klinghofer, E.F. Johnson, C.K. Donawho, D.J. Frost, V. Bontcheva-Diaz, J.J. Bouska, D.J. Osterling, A.M. Olson, K.C. Marsh, Y. Luo, and V.L. Giranda J. Med. Chem. 52 2009 514
29. R. Plummer, P. Lorigan, N. Steven, L. Scott, M.R. Middleton, R.H. Wilson, E. Mulligan, N. Curtin, D. Wang, R. Dewji, A. Abbattista, J. Gallo, and H. Calvert Cancer Chemother. Pharmacol. 71 2013 1191
30. P. Jones, S. Altamura, J. Boueres, F. Ferrigno, M. Fonsi, C. Giomini, S. Lamartina, E. Monteagudo, J.M. Ontoria, M.V. Orsale, M.C. Palumbi, S. Pesci, G. Roscilli, R. Scarpelli, C. Schultz-Fademrecht, C. Toniatti, and M. Rowley J. Med. Chem. 52 2009 7170
31. Y. Shen, F.L. Rehman, Y. Feng, J. Boshuizen, I. Bajrami, R. Elliott, B. Wang, C.J. Lord, L.E. Post, and A. Ashworth Clin. Cancer Res. 19 2013 5003
32. J. Ledermann, P. Harter, C. Gourley, M. Friedlander, I. Vergote, G. Rustin, C.L. Scott, W. Meier, R. Shapira-Frommer, T. Safra, D. Matei, A. Fielding, S. Spencer, B. Dougherty, M. Orr, D. Hodgson, J.C. Barrett, and U. Matulonis Lancet Oncol. 15 2014 852
33. N.J. Curtin Drug Discovery Today Dis. Models 9 2012 e51
34. J. Ishida, H. Yamamoto, Y. Kido, K. Kamijo, K. Murano, H. Miyake, M. Ohkubo, T. Kinoshita, M. Warizaya, A. Iwashita, K. Mihara, N. Matsuoka, and K. Hattori Bioorg. Med. Chem. 14 2006 1378
35. A. Ruf, J. Ménissier de Murcia, G. de Murcia, and G.E. Schulz Proc. Natl. Acad. Sci. U.S.A. 93 1996 7481
36. A. Ruf, G. de Murcia, and G.E. Schulz Biochemistry 37 1998 3893
37. L. Lehtiö, A.S. Jemth, R. Collins, O. Loseva, A. Johansson, N. Markova, M. Hammarström, A. Flores, L. Holmberg-Schiavone, J. Weigelt, T. Helleday, H. Schüler, and T. Karlberg J. Med. Chem. 52 2009 3108
38. L. Zhu, J. Jin, C. Liu, C. Zhang, Y. Sun, Y. Guo, D. Fu, X. Chen, and B. Xu Bioorg. Med. Chem. 19 2011 2797
39. S. Goto, H. Tsuboi, M. Kanoda, K. Mukai, and K. Kagara Org. Proc. Res. Dev. 7 2003 700
40. J. Yélamos, V. Schreiber, and F. Dantzer Trends Mol. Med. 14 2008 169
41. J.C. Amé, V. Rolli, V. Schreiber, C. Niedergang, F. Apiou, P. Decker, S. Muller, T. Höger, J. Ménissier-de Murcia, and G. de Murcia J. Biol. Chem. 274 1999 17860
42. P.T. Sunderland, E.C.Y. Woon, A. Dhami, A.B. Bergin, M.F. Mahon, P.J. Wood, L.A. Jones, S.R. Tully, M.D. Lloyd, A.S. Thompson, H. Javaid, N.M.B. Martin, and M.D. Threadgill J. Med. Chem. 54 2011 2049
43. S.A. Narod, and W.D. Foulkes Nat. Rev. Cancer 4 2004 665
44. A.M. Mendes-Pereira, S.A. Martin, R. Brough, A. McCarthy, J.R. Taylor, J.S. Kim, T. Waldman, C.J. Lord, and A. Ashworth EMBO Mol. Med. 1 2009 315
45. C.R. Gil del Alcazar, M.C. Hardebeck, B. Mukherjee, N. Tomimatsu, X. Gao, J. Yan, X.J. Xie, R. Bachoo, L. Li, A.A. Habib, and S. Burma Clin. Cancer Res. 20 2014 1235
46. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605
47. E.C. Meng, B.K. Shoichet, and I.D. Kuntz J. Comput. Chem. 13 1992 505
48. J.J. Irwin, and B.K. Shoichet J. Chem. Inf. Model. 45 2004 177
49. M.P. Jacobson, G.A. Kaminski, R.A. Friesner, and C.S. Rapp J. Phys. Chem. B 106 2002 11673
50. R. Cao, M. Liu, M. Yin, Q. Liu, Y. Wang, and N. Huang J. Chem. Inf. Model. 52 2012 2730
51. R. Cao, N. Huang, and Y. Wang J. Chem. Inf. Model. 54 2014 1987
52. Z. Zhu, J. Jin, N. Xue, X. Song, and X. Chen Anal. Biochem. 449 2014 188