Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

European Journal of Medicinal Chemistry

Volumn 50, Issue , 2012, Pages 264-273

  Kulkarni, Shridhar S ^a   Singh, Satyakam ^a   Shah, Janki R ^a   Low, Woon Kai ^a   Talele, Tanaji T ^a  

^a ST JOHN'S UNIVERSITY   (United States)

Author keywords

BRCA1; Docking; p53; PARP 1; Quinazolinone

Indexed keywords

5 CHLOROQUINAZOLIN 4(3H) ONE; 5 FLUORO 2 METHYLQUINAZOLIN 4(3H) ONE; 5 FLUOROQUINAZOLIN 4(3H) ONE; 5 METHYLQUINAZOLIN 4(3H) ONE; 6 AMINOQUINAZOLIN 4(3H) ONE; 6 CHLOROQUINAZOLIN 4(3H) ONE; 6 FLUOROQUINAZOLIN 4(3H) ONE; 6 METHYLQUINAZOLIN 4(3H) ONE; 6,7 DIFLUOROQUINAZOLIN 4(3H) ONE; 6,7 DIMETHOXYQUINAZOLIN 4(3H) ONE; 6,8 DIMETHYLQUINAZOLIN 4(3H) ONE; 7 AMINOQUINAZOLIN 4(3H) ONE; 7 CHLOROQUINAZOLIN 4(3H) ONE; 7 FLUOROQUINAZOLIN 4(3H) ONE; 7 METHYLQUINAZOLIN 4(3H) ONE; 7 NITROQUINAZOLIN 4(3H) ONE; 7 TRIFLUOROMETHYLQUINAZOLIN 4(3H) ONE; 8 AMINO 2 METHYLQUINAZOLIN 4(3H) ONE; 8 AMINOQUINAZOLIN 4(3H) ONE; 8 FLUOROQUINAZOLIN 4(3H) ONE; 8 METHYLQUINAZOLIN 4(3H) ONE; 8 NITROQUINAZOLIN 4(3H) ONE; 8 TRIFLUOROMETHYLQUINAZOLIN 4(3H) ONE; BRCA1 PROTEIN; GLYCOSYLTRANSFERASE INHIBITOR; METHYL GROUP; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; NICOTINAMIDE DERIVATIVE; QUINAZOLIN 4(3H) ONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; DRUG BINDING SITE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; IC 50; NONHUMAN; PROCESS OPTIMIZATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION LINE; WILD TYPE;

ANIMALS; BRCA1 PROTEIN; CELLS, CULTURED; EMBRYO, MAMMALIAN; ENZYME INHIBITORS; FIBROBLASTS; MICE; MICE, KNOCKOUT; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLY(ADP-RIBOSE) POLYMERASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862783558     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.001     Document Type: Article

References (35)

1. H. Otto, P.A. Reche, F. Bazan, K. Dittmar, F. Haag, and F. Koch-Nolte In silico characterization of the family of PARP-like poly(ADP-ribosyl)transferases (pARTs) BMC Genomics 6 2005 139
2. M. Audebert, B. Salles, and P. Calsou Involvement of poly(ADP-ribose) polymerase-1 and XRCC1/DNA ligase III in an alternative route for DNA double-strand breaks rejoining J. Biol. Chem. 279 2004 55117 55126
3. V. Schreiber, F. Dantzer, J. Ame, and M. de Gilbert Poly(ADP-ribose): novel functions for an old molecule Nat. Rev. Mol. Cell Biol. 7 2006 517 528
4. T.D. Penning, G. 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 Discovery of the poly(ADP-ribose) polymerase (PARP) Inhibitor 2-[(R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole-4-carboxamide (ABT-888) for the Treatment of Cancer J. Med. Chem. 52 2009 514 523
5. 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 Specific killing of BRCA2-deficient tumors with inhibitors of poly(ADP-ribose) polymerase Nature 434 2005 913 917
6. H. Farmer, N. McCabe, C.J. Lord, A.N.J. Tutt, D.A. Johnson, T.B. Richardson, M. Santarosa, K.J. Dillon, I. Hickson, C. Knights, N.M.B. Martin, S.P. Jackson, G.C.M. Smith, and A. Ashworth Targeting the DNA repair defect in BRCA mutant cells as a therapeutic strategy Nature 434 2005 917 921
7. R.J. Griffin, S. Srinivasan, K. Bowman, A.H. Calvert, N.J. Curtin, D.R. Newell, L.C. Pemberton, and B.T. Golding Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP) J. Med. Chem. 41 1998 5247 5256
8. R.J. Griffin, A.H. Calvert, N.J. Curtin, D.R. Newell, and B.T. Golding Preparation of benzamide analogs as poly(ADP-ribose)polymerase inhibitors, WO9524379A1 PCT Int. Appl. 1995 79
9. K. Hattori, Y. Kido, H. Yamamoto, J. Ishida, K. Kamijo, K. Murano, M. Ohkubo, T. Kinoshita, A. Iwashita, K. Mihara, S. Yamazaki, N. Matsuoka, Y. Teramura, and H. Miyake Rational approaches to discovery of orally active and brain-penetrable quinazolinone inhibitors of poly(ADP-ribose)polymerase J. Med. Chem. 47 2004 4151 4154
10. M. Banasik, H. Komura, M. Shimoyama, and K. Ueda Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase J. Biol. Chem. 267 1992 1569 1575
11. C.C. Price, N.J. Leonard, and D.Y. Curtin 4-(4-Diethylamino-1- methylbutylamino)-7-chloroquinazoline J. Am. Chem. Soc. 68 1946 1305 1306
12. F.D. Bellamy, and K. Ou Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium Tetrahedron Lett. 25 1984 839 842
13. J.B. Jiang, D.P. Hesson, B.A. Dusak, D.L. Dexter, G.J. Kang, and E. Hamel Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization J. Med. Chem. 33 1990 1721 1728
14. D. Ferraris, R.P. Ficco, D. Dain, M. Ginski, S. Lautar, K. Lee-Wisdom, S. Liang, Q. Lin, M.X. Lu, L. Morgan, B. Thomas, L.R. Williams, J. Zhang, Y. Zhou, and V.J. Kalish Design and synthesis of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. Part 4: biological evaluation of imidazobenzodiazepines as potent PARP-1 inhibitors for treatment of ischemic injuries Bioorg. Med. Chem. 11 2003 3695 3707
15. C.Y. Watson, W.J. Whish, and M.D. Threadgill Synthesis of 3-substituted benzamides and 5-substituted isoquinolin-1(2H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP) Bioorg. Med. Chem. 6 1998 721 734
16. A.W. White, R. Almassy, A.H. Calvert, N.J. Curtin, R.J. Griffin, Z. Hostomsky, K. Maegley, D.R. Newell, S. Srinivasan, and B.T. Golding Resistance-modifying agents. 9.1 synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase J. Med. Chem. 43 2000 4084 4097
17. M.J. Suto, W.R. Turner, C.M. Arundel-Suto, L.M. Werbel, and J.S. Sebolt-Leopold Dihydroisoquinolinones: the design and synthesis of a new series of potent inhibitors of poly(ADP-ribose) polymerase Anticancer Drug Des 6 1991 107 117
18. D. Bellocchi, A. Macchiarulo, G. Costantino, and R. Pellicciari Docking studies on PARP-1 inhibitors: insights into the role of a binding pocket water molecule Bioorg. Med. Chem. 13 2005 1151 1157
19. A. Ruf, V. Rolli, G. de Murcia, and G.E. Schulz The mechanism of the elongation and branching reaction of poly(ADP-ribose) polymerase as derived from crystal structures and mutagenesis J. Mol. Biol. 278 1998 57 65
20. M. Altmeyer, S. Messner, P.O. Hassa, M. Fey, and M.O. Hottiger Molecular mechanism of poly(ADP-ribosyl)ation by PARP1 and identification of lysine residues as ADP-ribose acceptor sites Nucleic Acids Res. 37 2009 3723 3738
21. S. Messner, M. Altmeyer, H. Zhao, A. Pozivil, B. Roschitzki, P. Gehrig, D. Rutishauser, D. Huang, A. Caflisch, and M.O. Hottiger PARP1 ADP-ribosylates lysine residues of the core histone tails Nucleic Acids Res. 38 2010 6350 6362
22. S.S. Haenni, P.O. Hassa, M. Altmeyer, M. Fey, R. Imhof, and M.O. Hottiger Identification of lysines 36 and 37 of PARP-2 as targets for acetylation and auto-ADP-ribosylation Int. J. Biochem. Cell Biol. 40 2008 2274 2283
23. S.F. Bunting, E. Callén, N. Wong, H.T. Chen, F. Polato, A. Gunn, A. Bothmer, N. Feldhahn, O. Fernandez-Capetillo, L. Cao, X. Xu, C.X. Deng, T. Finkel, M. Nussenzweig, J.M. Stark, and A. Nussenzweig 53BP1 inhibits homologous recombination in Brca1-deficient cells by blocking resection of DNA breaks Cell 141 2010 243 254
24. G.E. Abdelkarim, K. Gertz, C. Harms, J. Katchanov, U. Dirnagl, C. Szabo, and M. Endres Protective effects of PJ34, a novel, potent inhibitor of poly(ADP-ribose) polymerase (PARP) in in vitro and in vivo models of stroke Int. J. Mol. Med. 7 2001 255 260
25. F.G. Soriano, L. Virag, P. Jagtap, E. Szabo, J.G. Mabley, L. Liaudet, A. Marton, D.G. Hoyt, K.G.K. Murthy, A.L. Salzman, G.J. Southan, and C. Szabo Diabetic endothelial dysfunction: the role of poly(ADP-ribose) polymerase activation Nat. Med. 7 2001 108 113
26. A.R. Venkitaraman Tracing the network connecting BRCA and Fanconi anaemia proteins Nat. Rev. Cancer 4 2004 266 276
27. L. Orfi, F. Waczek, J. Pato, I. Varga, B. Hegymegi-Barakonyi, R.A. Houghten, and G. Keri Improved, high yield synthesis of 3H-quinazolin-4-ones, the key intermediates of recently developed drugs Curr. Med. Chem. 11 2004 2549 2553
28. J.B. Hynes, S.A. Patil, R.L. Hagan, A. Cole, W. Kohler, and J.H. Freisheim Comparison of the biological effects of selected 5,8-dideazafolate analogues with their 2-desamino counterparts J. Med. Chem. 32 1989 852 856
29. E.A. Glazer Preparation of Trans-3-[3-(3-hydroxt-2-piperidinyl)-2- oxopropyl]quinazolin-4(3H)-ones as Anticoccidial Agents US4762838A, U. S 1988 17
30. Y. Wu, and C.S. Hamilton Arsenicals containing quinoline and quinazoline nuclei J. Am. Chem. Soc. 74 1952 1863 1864
31. R.A. LeMahieu, M. Carson, W.C. Nason, D.R. Parrish, A.F. Welton, H.W. Baruth, and B. Yaremko (E)-3-(4-Oxo-4H-quinazolin-3-yl)-2-propenoic acids, a new series of antiallergy agents J. Med. Chem. 26 1983 420 425
32. M. Okano, J. Mito, Y. Maruyama, H. Masuda, T. Niwa, S. Nakagawa, Y. Nakamura, and A. Matsuura Discovery and structure-activity relationships of 4-aminoquinazoline derivatives, a novel class of opioid receptor like-1 (ORL1) antagonists Bioorg. Med. Chem. 17 2009 119 132
33. V.S. Dighe, S. Somasekhara, G. Bagavant, and S.L. Mukherjee 3-Aminoquinazolinones and their derivatives Curr. Sci. 33 1964 78 80
34. T. Bhattacharyya, P.K. Bose, and J.N. Ray A new synthesis of quinazolines. I J. Indian Chem. Soc. 6 1929 279 287
35. V.S. Patel, and S.R. Patel Niementowski 4-oxoquinazoline synthesis: modification and mechanism. II. Synthesis of substituted 5,6,7 and 8-chloro-3(H)-4-oxoquinazolines J. Indian Chem. Soc. 45 1968 167 170