A facile intramolecular azido/amido reductive cyclization approach: synthesis of pyrrolobenzodiazepines and their dimers

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1465-1468

  Kamal, Ahmed ^a   Shankaraiah, N ^a   Markandeya, N ^b   Reddy, K Laxma ^a   Reddy, Ch Sanjeeva ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KAKATIYA UNIVERSITY   (India)

Author keywords

Amides; Azides; Intramolecular reductive cyclization; LiAlH4; LiBH4; Pyrrolo 2,1 c 1,4 benzodiazepines

Indexed keywords

ALUMINUM DERIVATIVE; AMIDE; AROMATIC COMPOUND; AZIDE; BENZODIAZEPINE DERIVATIVE; DIMER; IMINE; LITHIUM DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; DIMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; REDUCTION; SYNTHESIS;

EID: 38649096649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.004     Document Type: Article

References (38)

1. Trauger J.W., Baird E.E., and Dervan P.B. J. Am. Chem. Soc. 120 (1998) 3534-3535
2. White S., Szewczyk J.W., Turner J.M., Baird E.E., and Dervan P.B. Nature 391 (1998) 468-471
3. Kielkopf C.L., White S., Szewczyk J.W., Turner J.M., Baird E.E., Dervan P.B., and Rees D.C. Science 282 (1998) 111-115
4. Dervan P.B. FASEB 11 (1997) 2546
5. Turner J.M., Baird E.E., and Dervan P.B. J. Am. Chem. Soc. 119 (1997) 7636-7644
6. Wemmer D.E., and Dervan P.B. Curr. Opin. Struct. Biol. 7 (1997) 355-361
7. Gottesfeld J.M., Neely L., Trauger J.W., Baird E.E., and Dervan P.B. Nature 387 (1997) 202-205
8. Szewczyk J.W., Baird E.E., and Dervan P.B. Angew. Chem., Int. Ed. 35 (1996) 1487-1489
9. Thurston D.E. In: Neidle S., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug-DNA Interactions Vol. 1 (1993), Macmillan Press Ltd, Basingstoke, Hants, UK 54-88
10. Remers W.A. The Chemistry of Antitumor Antibiotics Vol. 2 (1988), Wiley-Interscience, New York pp 28-92
11. Hurley L.H., and Thurston D.E. Pharm. Res. 2 (1984) 52-59
12. Thurston D.E., and Bose D.S. Chem. Rev. 94 (1994) 433-465
13. Bose D.S., Thompson A.S., Ching J.S., Hartley J.A., Berardini M.D., Jenkins T.C., Neidle S., Hurley L.H., and Thurston D.E. J. Am. Chem. Soc. 114 (1992) 4939-4941
14. Thurston D.E., Bose D.S., Thompson A.S., Howard P.W., Leoni A., Croker S.J., Jenkins T.C., Neidle S., Hartley J.A., and Hurley L.H. J. Org. Chem. 61 (1996) 8141-8147
15. Bose D.S., Thompson A.S., Ching J.A., Hartley J.A., Berardini M.D., Jenkins T.C., Neidle S., Hurley L.H., and Thurston D.E. J. Am. Chem. Soc. 114 (1992) 4939-4941
16. Bose D.S., Thompson A.S., Smellie M., Berardini M.D., Hartley J.A., Jenkins T.C., Neidle S., and Thurston D.E. J. Chem. Soc., Chem. Commun. (1992) 1518-1520
17. Gregson S.J., Howard P.W., Hartley J.A., Brooks A.A., Adams L.J., Jenkins T.C., Kelland L.R., and Thurston D.E. J. Med. Chem. 44 (2001) 737-748
18. Gregson S.J., Howard P.W., Gullick D.R., Hamaguchi A., Corcoran K.E., Brooks N.A., Hartley J.A., Jenkins T.C., Patel S., Guille M.J., and Thurston D.E. J. Med. Chem. 47 (2004) 1161-1174
19. Kamal A., Reddy K.L., Devaiah V., and Shankaraiah N. Synlett (2004) 2533-2536
20. Kamal A., Devaiah V., Reddy K.L., and Shankaraiah N. Adv. Synth. Catal. 348 (2006) 249-254
21. Kamal A., Reddy K.L., Devaiah V., Shankaraiah N., and Reddy D.R.S. Mini-Rev. Med. Chem. 6 (2006) 53-68
22. Kamal A., Reddy K.L., Devaiah V., Shankaraiah N., Reddy G.S.K., and Raghavan S. J. Comb. Chem. 9 (2007) 29-42
23. Kamal A., Shankaraiah N., Devaiah V., and Reddy K.L. Tetrahedron Lett. 47 (2006) 6553-6556
24. Kamal A., Shankaraiah N., Reddy K.L., and Devaiah V. Tetrahedron Lett. 47 (2006) 4253-4257
25. Kamal A., Reddy K.L., Devaiah V., and Shankaraiah N. Synlett (2004) 1841-1843
26. Kamal A., Rao M.V., and Reddy B.S.N. Khim. Geterotsikl. (Chem. Heterocycl. Compd.) (1998) 1588-1604
27. Kamal A., Rao M.V., Laxman N., Ramesh G., and Reddy G.S.K. Curr. Med. Chem.-Anti-Cancer Agents 2 (2002) 215-254
28. Kaneko T., Wong H., Doyle T.W., Rose W.C., and Bradner W.T. J. Med. Chem. 28 (1985) 388-392
29. Langley D.R., and Thurston D.E. J. Org. Chem. 52 (1987) 91-97
30. Courtney S.M., and Thurston D.E. Tetrahedron Lett. 34 (1993) 5327-5328
31. Bose D.S., Jones G.B., and Thurston D.E. Tetrahedron 48 (1992) 751-758
32. Kamal A., Reddy P.S.M.M., and Reddy D.R. Tetrahedron Lett. 44 (2003) 2857-2860
33. Kamal A., Ramana A.V., Reddy K.S., Ramana K.V., Babu A.H., and Prasad B.R. Tetrahedron Lett. 45 (2004) 8187-8190
34. Kamal A., Reddy K.S., Prasad B.R., Babu A.H., and Ramana A.V. Tetrahedron Lett. 45 (2004) 6517-6521
35. Budyka M.F., Biktimirova N.V., and Gavrishova T.N. Chem. Heterocycl. Compd. 43 (2007) 454-459
36. +) 738.4472, found 738.4450.
37. +) 560.3833, found 560.3812.
38. Kamal A., Shankaraiah N., Devaiah V., and Reddy K.L. Tetrahedron Lett. 47 (2006) 9025-9028