Synthesis by radical cyclization and cytotoxicity of highly potent bioreductive alicyclic ring fused [1,2-a]benzimidazolequinones

Chemistry - A European Journal

Volumn 13, Issue 11, 2007, Pages 3218-3226

  Lynch, Mary ^a   Hehir, Sarah ^a   Kavanagh, Paul ^a   Leech, Dónal ^a   O'Shaughnessy, John ^a   Carty, Michael P ^a   Aldabbagh, Fawaz ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

Antitumor agents; Benzimidazolequinones; Radicals; Synthetic methods

Indexed keywords

BIOASSAY; CYTOTOXICITY; FIBROBLASTS; NUCLEOPHILES; SYNTHESIS (CHEMICAL); TUMORS;

ANTITUMOR AGENTS; BENZIMIDAZOLEQUINONES; CYCLOHEXANECARBONITRILE; SYNTHETIC METHODS;

AROMATIC COMPOUNDS;

BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DRUG EFFECT; FIBROBLAST; HUMAN; SKIN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BENZIMIDAZOLES; CELL PROLIFERATION; CELLS, CULTURED; CYCLIZATION; FIBROBLASTS; HUMANS; MOLECULAR STRUCTURE; QUINONES; SKIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34250632264     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601450     Document Type: Article

References (39)

1. a) R. H. J. Hargreaves, J. A. Hartley, J. Butler, Front. Biosci. 2000, 5, e172-180;
2. b) M. A. Naylor, P. Thomson, Mini-Rev. Med. Chem. 2001, 1, 17-29;
3. c) M. Jaffar, N. Abou-Zeid, L. Bai, I. Mrema, I. Robinson, R. Tanner, I.J. Stratford, Curr. Drug Delivery 2004, 1, 345-350.
4. S. E. Wolkenberg, D. L. Boger, Chem. Rev. 2002, 102, 2477-2495.
5. a) C. J. Moody, N. O'Sullivan, I. J. Stratford, M. A. Stephens, P. Workman, S. M. Bailey, A. Lewis, Anti-Cancer Drugs 1994, 5, 367-372;
6. b) A. S. Cotterill, C. J. Moody, R. J. Mortimer, C. L. Norton, N. O'Sullivan, M. A. Stephens, N. R. Stradiotto, E. Swann, I. J. Stratford, J. Med. Chem. 1994, 37, 3834-3843.
7. C. J. Moody, C. L. Norton, A. M. Z. Slawin, S. Taylor, Anti-Cancer Drug Des. 1998, 13, 611-634.
8. M. A. Naylor, M. Jaffar, J. Nolan, M. A. Stephens, S. Butler, K. B. Patel, S. A. Everett, G. E. Adams, I. J. Stratford, J. Med. Chem. 1997, 40, 2335-2346.
9. M. A. Naylor, E. Swann, S. A. Everett, M. Jaffar, J. Nolan, N. Robertson, S. D. Lockyer, K. B. Patel, M. F. Dennis, M. R. L. Stratford, P. Wardman, G. E. Adams, C. J. Moody, I. J. Stratford, J. Med. Chem. 1998, 41, 2720-2731.
10. B. M. Hoey, J. Butler, A. J. Swallow, Biochemistry 1988, 27, 2608-2614.
11. a) J. O'Shaughnessy, D. Cunningham, P. Kavanagh, D. Leech, P. McArdle, F. Aldabbagh, Synlett 2004, 2382-2384;
12. b) J. O'Shaughnessy, F. Aldabbagh, Synthesis 2005, 1069-1076.
13. a) W. G. Schulz, I. Islam, E. B. Skibo, J. Med. Chem. 1995, 38, 109-118;
14. b) E. B. Skibo, I. Islam, W.G. Schulz, R. Zhou, L. Bess, R. Boruah, Synlett 1996, 297-309;
15. c) E. B. Skibo, S. Gordon, L. Bess, R. Boruah, M.J. Heileman, J. Med. Chem. 1997, 40, 1327-1329;
16. d) A. Suleman, E. B. Skibo, J. Med. Chem. 2002, 45, 1211-1220.
17. C. Flader, J. Liu, R. F. Borch, J. Med. Chem. 2000, 43, 3157-3167.
18. a) I. Antonini, F. Claudi, G. Cristalli, P. Franchetti, M. Grifantini, S. Martelli, J. Med. Chem. 1988, 31, 260-264;
19. b) A. K. Singh, J.W. Lown, Anti-Cancer Drug Des. 2000, 15, 265-275.
20. S. Hehir, M. Lynch, L. O'Donovan, M. P. Carty, F. Aldabbagh, unpublished results.
21. F. Gagosz, S. Z. Zard, Org. Lett. 2002, 4, 4345-4348.
22. A. L. J. Beckwith, V. W. Bowry, W. R. Bowman, E. Mann, J. Parr, J. M. D. Storey, Angew. Chem. 2004, 116, 97-100;
23. Angew. Chem. Int. Ed. 2004, 43, 95-98.
24. P. T. F. McLoughlin, M. A. Clyne, F. Aldabbagh, Tetrahedron 2004, 60, 8065-8071.
25. a) M. A. Clyne, F. Aldabbagh, Org. Biomol. Chem. 2006, 4, 268-277;
26. b) F. Aldabbagh, M. A. Clyne, Lett. Org. Chem. 2006, 3, 510-513.
27. L. Weinberger, A. R. Day, J. Org. Chem. 1959, 24, 1451-1454.
28. a) F. Aldabbagh, W. R. Bowman, Tetrahedron Lett. 1997, 38, 3793-3794;
29. b) F. Aldabbagh, W. R. Bowman, Tetrahedron 1999, 55, 4109-4122.
30. S. M. Allin, W. R. Bowman, R. Karim, S.S. Rahman, Tetrahedron 2006, 152, 4306-4316.
31. K. W. Dixon in Polymer Handbook (Eds.; J. Brandrup, E. H. Immergut, E. A. E. Grulke), Wiley. New York, 4th ed., 1999, pp. 1-76.
32. a) D. C. Harrowven, I. L. Guy, Chem. Commun. 2004, 1968-1969;
33. b) B. S. Edelson, B. M. Stoltz, E. J. Corey, Tetrahedron Lett. 1999, 40, 6729-6730.
34. J. E. Leibner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450.
35. M. Lynch, PhD thesis. National University of Ireland, Galway, 2007.
36. I. Antonini, G. Cristalli, P. Franchetti, M. Grifantini, S. Martelli, Heterocycles 1982, 19, 2313-2317.
37. a) J. W. Lown, H. -h. Chen, Can. J. Chem. 1981, 59, 390-395;
38. b) L. Durse, S. Rajagopalan, H. M. Eliot, J. M. Covey, B. K. Sinha, Cancer Res. 1990, 50, 648-652.
39. A. R. Freedman, D. S. Payne, A. R. Day, J. Heterocycl. Chem. 1966, 3, 257-259.