Dibenzo[c,h][1,5]naphthyridinediones as topoisomerase i inhibitors: Design, synthesis, and biological evaluation

Journal of Organic Chemistry

Volumn 77, Issue 11, 2012, Pages 5167-5172

  Kiselev, Evgeny ^a   Empey, Nicholas ^a   Agama, Keli ^b   Pommier, Yves ^b   Cushman, Mark ^a  

^a PURDUE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL EVALUATION; INHIBITORY ACTIVITY; SYNTHETIC PATHWAYS; TOPOISOMERASE I;

CHEMISTRY;

ORGANIC COMPOUNDS;

11 [3 (1H IMIDAZOL 1 YL) PROPYL] 2,3 DIMETHOXYDIBENZO (1,5) NAPHTHYRIDINE 6,12 (5H,11H) DIONE; 2 (3' CHLOROPROPYL) 6,7 DIMETHOXY 3 (2' METHOXYCARBONYL PHENYL) 1 OXO 1,2 DIHYDROISOQUINOLINE; 2 (3' CHLOROPROPYL) 6,7 DIMETHOXY 3 (2' METHOXYCARBONYL PHENYL) 1 OXO 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 FORMYLBENZOIC ACID METHYL ESTER; 2,3 DIMETHOXY 11 (3 MORPHOLINOPROPYL) DIBENZO (1,5) NAPHTHYRIDINE 6,12 (5H,11H) DIONE; 6,7 DIMETHOXY 3 (2' METHOXYCARBONYLPHENYL) 2 (3' IODOPROPYL) 4 NITRO 1 OXO 1,2 DIHYDROISOQUINOLINE; DIBENZO (1,5) NAPHTHYRIDINEDIONE DERIVATIVE; DNA TOPOISOMERASE; DNA TOPOISOMERASE INHIBITOR; METHYL 2 [(3 CHLOROPROPYLIMINO) METHYL] BENZOATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR MODEL;

DNA TOPOISOMERASES, TYPE I; DRUG SCREENING ASSAYS, ANTITUMOR; ISOQUINOLINES; MODELS, MOLECULAR; NAPHTHYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE I INHIBITORS;

EID: 84861831409     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3006039     Document Type: Article

References (30)

1. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888-3890
2. Pommier, Y.; Leo, E.; Zhang, H. L.; Marchand, C. Chem. Biol. 2010, 17, 421-433
3. Pommier, Y. Nat. Rev. Cancer 2006, 6, 789-802
4. Sheng, C. Q.; Miao, Z. Y.; Zhang, W. N. Curr. Med. Chem. 2011, 18, 4389-4409
5. Drwal, M. N.; Agama, K.; Wakelin, L. P. G.; Pommier, Y.; Griffith, R. PLoS One 2011, 6, e25150
6. Pommier, Y.; Cushman, M. Mol. Cancer Ther. 2009, 8, 1008-1014
7. Kiselev, E.; Dexheimer, T. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2010, 53, 8716-8726
8. Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 3781-3783
9. Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 286-288
10. Ruchelman, A. L.; Singh, S. K.; Ray, A.; Wu, X. H.; Yang, J. M.; Li, T. K.; Liu, A.; Liu, L. F.; LaVoie, E. J. Bioorg. Med. Chem. 2003, 11, 2061-2073
11. Genes, C.; Michel, S.; Tillequin, F.; Poree, F. H. Tetrahedron 2009, 65, 10009-10015
12. Erve, A.; Saoudi, Y.; Thirot, S.; Guetta-Landras, C.; Florent, J. C.; Nguyen, C. H.; Grierson, D. S.; Popov, A. V. Nucleic Acids Res. 2006, 34, e43
13. Wang, L. K.; Johnson, R. K.; Hecht, S. M. Chem. Res. Toxicol. 1993, 6, 813-818
14. Li, T. K.; Houghton, P. J.; Desai, S. D.; Daroui, P.; Liu, A. A.; Hars, E. S.; Ruchelman, A. L.; LaVoie, E. J.; Liu, L. F. Cancer Res. 2003, 63, 8400-8407
15. Genes, C.; Lenglet, G.; Depauw, S.; Nhili, R.; Prado, S.; David-Cordonnier, M. H.; Michel, S.; Tillequin, F.; Poree, F. H. Eur. J. Med. Chem. 2011, 46, 2117-2131
16. Bisagni, E.; Landras, C.; Thirot, S.; Huel, C. Tetrahedron 1996, 52, 10427-10440
17. Osuka, A.; Nakajima, S.; Maruyama, K. J. Org. Chem. 1992, 57, 7355-7359
18. Potts, K. T.; Robinson, R. J Chem Soc 1955, 2675-2686
19. Cushman, M.; Wong, W. C. J. Org. Chem. 1984, 49, 1278-1280
20. Cushman, M.; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873-2879
21. Cushman, M.; Choong, T. C.; Valko, J. T.; Koleck, M. P. J. Org. Chem. 1980, 45, 5067-5073
22. Westcott, S. A.; Zhang, H.; Vogels, C. M.; Wheaton, S. L.; Baerlocher, F. J.; Decken, A. Synthesis 2005, 2739-2743
23. Vara, Y.; Bello, T.; Aldaba, E.; Arrieta, A.; Pizarro, J. L.; Arriortua, M. I.; Lopez, X.; Cossio, F. P. Org. Lett. 2008, 10, 4759-4762
24. Xiao, X. S.; Cushman, M. J. Org. Chem. 2005, 70, 6496-6498
25. Dexheimer, T. S.; Pommier, Y. Nat. Protoc. 2008, 3, 1736-1750
26. Pfister, T. D.; Reinhold, W. C.; Agama, K.; Gupta, S.; Khin, S. A.; Kinders, R. J.; Parchment, R. E.; Tomaszewski, J. E.; Doroshow, J. H.; Pommier, Y. Mol. Cancer Ther. 2009, 8, 1878-1884
27. Morrell, A.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. Lett. 2006, 16, 1846-1849
28. Pourquier, P.; Ueng, L. M.; Fertala, J.; Wang, D.; Park, H. J.; Essigmann, J. M.; Bjornsti, M. A.; Pommier, Y. J. Biol. Chem. 1999, 274, 8516-8523
29. SYBYL 8.0, Tripos Int.: St. Louis.
30. Verdonk, M. L.; Cole, J. C.; Hartshorn, M. J.; Murray, C. W.; Taylor, R. D. Proteins 2003, 52, 609-623