Synthesis of aryl- and heteroaryl[a]pyrrolo[3,4-c]carbazoles

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 8008-8014

  Sanchez Martinez, Concha ^a   Faul, Margaret M ^b   Shih, Chuan ^c   Sullivan, Kevin A ^b   Grutsch, John L ^b   Cooper, Jeremy T ^b   Kolis, Stanley P ^b  

^a DAEDALUS Data Decisions and Language SA   (Spain)

^b ELI LILLY AND COMPANY   (United States)

^c Chem Proc Research and Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; OXIDATION; SYNTHESIS (CHEMICAL);

REACTION CONDITIONS;

ORGANIC COMPOUNDS;

2 NAPHTHYLINDOLYLMALEIMIDE; CARBAZOLE DERIVATIVE; HETERO[1]PYRROLO[3,4 C]CARBAZOLE; MALEIMIDE DERIVATIVE; NAPHTHYL GROUP; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; PHOTOOXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0142058549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034207x     Document Type: Article

References (32)

1. Pindur, U.; Kim, Y.-S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29-69.
2. Kojiri, K.; Kondo, H.; Yoshinari, T.; Arakawa, H.; Nakajima, S.; Satoh, F.; Kawamura, K.; Okura, A.; Suda, H.; Okanishi, M. J. Antibiot. 1991, 44, 723-728.
3. Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844.
4. Slater, M. J.; Cockerill, S.; Baxter, R.; Bonser, R. W.; Gohil, K.; Gowrie, C.; Robinson, J. E.; Littler, E.; Parry, N.; Randall, R.; Snowden, W. Bioorg. Med. Chem. 1999, 7, 1067-1074.
5. Pereira, E. R.; Belin, L.; Sancelme, M,; Prudhomme, M.; Ollier, M.; Rapp, M.; Severe, D.; Riou, J.-F.; Fabbro, D.; Meyer, T. J. Med. Chem. 1996, 39, 4471-4477.
6. Trinks, U.; Buchdunger, E.; Furet, P.; Kump, W.; Mett, H.; Meyer, T.; Mueller, M.; Regenass, U.; Rihs, G.; Lydon, N.; Traxler, P. J. Med. Chem. 1994, 37, 1015-1027.
7. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792-798.
8. Zhu, G.; Conner, S. E.; Zhou, X.; Shih, C.; Li, T.; Brooks, H. B.; Considine, E.; Dempsey, J. A.; Faul, M. M.; Ogg, C.; Patel, B.; Schultz, R. M.; Spencer, C. D.; Teicher, B.; Watkins, S. A. J. Med. Chem. 2003, 46, 2027-2030.
9. Berlinck, R. G. S.; Britton, R.; Piers, E.; Lim, L.; Roberge, M.; Moreira da Rocha, R.; Andersen, R. J. J. Org. Chem. 1998, 63, 9850-9856.
10. Piers, E.; Britton, R.; Andersen, R. J. J. Org. Chem. 2000, 65, 530-535.
11. Bergman, J.; Desarbre, E.; Koch, E. Tetrahedron 1999, 55, 2363-2370.
12. Zhu; G.; Conner, S.; Zhou, X.; Shih, C.; Brooks, H. B.; Considine, E.; Dempse, J. A.; Ogg, C.; Patel, B.; Schultz, R. M.; Spencer, C. D.; Teicher, B.; Watkins, S. A. Bioorg. Med. Chem. Lett. 2003, 13, 1231-1235.
13. Hudkins, R. L. In Book of Abstracts, 212th ACS National Meeting, Orlando, FL, ORGN-320, 1996.
14. Janosik, T.; Bergman, J. Tetrahedron 1999, 55, 2371-2380.
15. Sanchez-Martinez, C.; Shih, C.; Faul, M. M.; Zhu, G.; Paal, M.; Somoza, C.; Li, T.; Krumrich, C.; Winneroski, L.; Xun, Z.; Brooks, H. B.; Patel, P.; Schultz, R. M.; DeHahn, T. D.; Kirmani, K.; Spencer, C. D.; Watkins, S. A.; Considine, E.; Dempsey, J. A.; Ogg, C. Bioorg. Med. Chem. Lett. 2003, in press.
16. Gallant, M.; Link, J. T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 343-349.
17. Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015-4018.
18. Link, J. T.; Gallant, M.; Danishefsky, S. J.; Huber, S. J. Am. Chem. Soc. 1993, 115, 3782-3783.
19. Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555-5558.
20. Joyce, R. P.; Gainor, J. A.; Weinreb, S. M. T. Org. Chem. 1987, 52, 1177-1185.
21. Kleinschroth, J.; Hartenstein, J.; Rudolph, C.; Schaechtele, C. Bioorg. Med. Chem. Lett. 1995, 5, 55-60.
22. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Morishima, H. Tetrahedron 1996, 52, 8099-8112.
23. Harris, W.; Hill, C. H.; Keech, E.; Malsher, P, Tetrahedron Lett. 1993, 34, 8361-8364.
24. Ohkubo, M.; Kawamoto, H.; Ohno, T.; Nakano, M.; Morishima, H. Tetrahedron 1997, 53, 585-592.
25. Faul, M. M.; Sullivan, K. A. Tetrahedron. Lett. 2001, 42, 3271-3273.
26. Routier, S.; Coudert, G.; Merour, J.-Y. Tetrahedron Lett. 2001, 42, 7025-7028.
27. Brewster, J. H.; Eliel, E. L. Org. React. 1953, VII, 99-197.
28. Kozikowski, A. P.; Ishida, H, Heterocycles 1980, 14, 55-58.
29. Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. Tetrahedron Lett. 1999, 40, 1109-1112.
30. Moody, C. J.; Rahimtoola, K. F.; Porter, B.; Ross, B. C. J. Org. Chem. 1992, 57, 2105-2114.
31. Sharifi, A.; Mohsenzadeh, F.; Mojtahedi, M. M.; Saidi, M. R.; Balalaie, S. Synth. Commun. 2001, 31, 431-434.
32. Kametani, T.; Satoh, F.; Agui, H.; Ueki, K.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Horie, S. Chem. Pharm. Bull. 1970, 18, 1161-1167.