Synthesis of benzimidazolequinone analogue of cyclopropamitosene antitumor agents

Synlett

Volumn , Issue 13, 2004, Pages 2382-2384

  O'Shaughnessy, John ^a   Cunningham, Desmond ^a   Kavanagh, Paul ^a   Leech, Dónal ^a   McArdle, Patrick ^a   Aldabbagh, Fawaz ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

Benzimidazoles; Bioreductive; Diazo compounds; Heterocycles; Hydrazones

Indexed keywords

ANTINEOPLASTIC AGENT; BENZIMIDAZOLE 2 ESCHENMOSER HYDRAZONE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZIMIDAZOLEQUINONE; CYCLOPROPAMITOSENE DERIVATIVE; CYCLOPROPANE; CYCLOPROPAPYRROLO[1,2 A]BENZIMIDAZOLEQUINONE; MITOMYCIN C; PYRIDO[1,2,A]BENZIMIDAZOLE; PYRROLO[1,2 A]BENZIMIDAZOLE; PYRROLO[1,2 A]BENZIMIDAZOLEQUINONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; CYCLOADDITION; DRUG MECHANISM; DRUG SYNTHESIS; REDUCTION; X RAY ANALYSIS;

EID: 8644223222     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831341     Document Type: Article

References (21)

1. Wolkenberg, S. E.; Boger, D. L. Chem. Rev. 2002, 102, 2477.
2. (a) Jones, G. B.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1989, 2449.
3. (b) Jones, G. B.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1989, 2455.
4. (c) Jones, G. B.; Moody, C. J.; Padwa, A.; Kassir, J. M. J. Chem. Soc., Perkin Trans. 1 1991, 1721.
5. (d) Cotterill, A. S.; Hartopp, P.; Jones, G. B.; Moody, C. J.; Norton, C. L.; O'Sullivan, N.; Swann, E. Tetrahedron 1994, 50, 7657.
6. (a) Cotterill, A. S.; Moody, C. J.; Mortimer, R. J.; Norton, C. L.; O'Sullivan, N.; Stephens, M. A.; Stradiotto, N. R.; Swann, E.; Stratford, I. J. J. Med. Chem. 1994, 37, 3834.
7. (b) Moody, C. J.; O'Sullivan, N.; Stratford, I. J.; Stephens, M. A.; Workman, P.; Bailey, S. M.; Lewis, A. Anti-Cancer Drugs 1994, 5, 367.
8. (c) Moody, C. J.; Norton, C. L.; Slawin, A. M. Z.; Taylor, S. Anti-Cancer Drug Design 1998, 13, 611.
9. Antonini, I.; Claudi, F.; Cristalli, G.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Med. Chem. 1988, 31, 260.
10. Representative papers: (a) Schulz, W. G.; Islam, I.; Skibo, E. B. J. Med. Chem. 1995, 38, 109.
11. (b) Skibo, E. B.; Islam, I.; Schulz, W. G.; Zhou, R.; Bess, L.; Boruah, R. Synlett 1996, 297.
12. (c) Skibo, E. B.; Gordon, S.; Bess, L.; Boruah, R.; Heileman, M. J. J. Med. Chem. 1997, 40, 1327.
13. (d) Craigo, W. A.; LeSueur, B. W.; Skibo, E. B. J. Med. Chem. 1999, 42, 3324.
14. Felix, D.; Muller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 1276.
15. 2: 184.1001; found: 184.0998.
16. The X-ray data of 3,3a,4,10b-tetrahydropyrazolo[3′,4′:3,4] pyrrolo[1,2-a]benzimidazole (8) has been deposited in the Cambridge Crystallographic Centre.
17. (a) Weinberger, L.; Day, A. R. J. Org. Chem. 1959, 24, 1451.
18. (b) Shaikh, I. A.; Johnson, F.; Grollman, A. P. J. Med. Chem. 1986, 29, 1329.
19. (c) Nose, M.; Suzuki, H. Synthesis 2000, 1539.
20. Gawinecki, R.; Omialowski, B.; Kolehmainen, E.; Janota, H. Heterocycl. Commun. 2003, 9, 275.
21. +; found: 199.0503.