Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 22, 2004, Pages 5699-5702

  Kamal, Ahmed ^a   Reddy, P S M M ^a   Reddy, D Rajasekhar ^a   Laxman, E ^a   Murthy, Y L N ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b ANDHRA UNIVERSITY   (India)

Author keywords

C2 exo fluorounsaturated pyrrolobenzodiazepine; DNA binding ability

Indexed keywords

BENZODIAZEPINE DERIVATIVE; SJG 136;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; DNA BINDING; DRUG SYNTHESIS; FLUORINATION; MOLECULAR MODEL; REACTION ANALYSIS;

BENZODIAZEPINES; BENZODIAZEPINONES; BINDING SITES; DNA; FLUORINE COMPOUNDS; MOLECULAR CONFORMATION; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 5144228623     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.08.050     Document Type: Article

References (40)

1. P.B. Dervan Science 232 1986 464
2. L.H. Hurley, and F.L. Boyd TIPS 9 1988 402
3. L.H. Hurley J. Med. Chem. 32 1989 2027
4. L.H. Hurley, and D.E. Thurston Pharm. Res. 1984 52
5. L.H. Hurley J. Antibiot. 30 1977 349
6. H. Aoki, N. Miyairi, M. Ajisaka, and H. Sakai J. Antibiot. 22 1969 201
7. X.-L. Yang, and A.H.-J. Wang Phramacol. Ther. 83 1999 181
8. S.J. Gregson, P.W. Howard, T.C. Jenkins, L.R. Kelland, and D.E. Thurston Chem. Commun. 1999 797
9. S.J. Gregson, P.W. Howard, J.A. Hartely, N.A. Brooks, L.J. Adams, T.C. Jenkins, L.R. Kelland, and D.E. Thurston J. Med. Chem. 44 2001 737
10. S.J. Gregson, P.W. Howard, D.R. Gullick, A. Hamaguchi, K.E. Corcoran, N.A. Brooks, J.A. Hartely, T.C. Jenkins, S. Patel, M.J. Guille, and D.E. Thurston J. Med. Chem. 47 2004 1161
11. D.E. Thurston, D.S. Bose, A.S. Thompson, P.W. Howard, A. Leoni, S.J. Crocker, T.C. Jenkins, S. Neidle, J.A. Hartley, and L.H. Hurley Synthesis of sequency-selective C8-linked pyrrolo[2,1-c][1,4]benzodiazepine DNA interstarnd cross-linking agents J. Org. Chem. 61 1996 8141
12. L.W. Hertel, J.S. Kroin, J.W. Misner, and J.M. Tustin J. Org. Chem. 53 1988 2406
13. L.W. Hertel, G.B. Boder, J.S. Kroin, S.M. Rinzel, G.A. Poore, G.C. Todd, and G.B. Grindey Cancer Res. 50 1990 4417
14. Y. Yoshimura, K. Kitano, H. Satoh, M. Watanabe, S. Miura, S. Sakata, T. Sasaki, and A. Matsuda J. Org. Chem. 61 1996 822
15. Y. Yoshimura, K. Kitano, K. Yamada, H. Satoh, M. Watanabe, S. Miura, S. Sakata, T. Sasaki, and A. Matsuda J. Org. Chem. 62 1997 3140
16. P.N. Edwards R.E. Banks B.E. Smart J.C. Tatlow Organofluorine Chemistry: Principles and Commercial Applications 1994 Plenum New York 501
17. I. Ojima J.R. McCarthy J.T. Welch Biomedical Frontiers of Fluorine Chemistry ACS Symposium Series 639 1996 American Chemical Society Washington
18. J.T. Welch, and S. Eswarakrishnan Fluorine in Bioorganic Chemistry 1991 John Wiley and Sons New York
19. R. Filler Asymmetric Fluoroorganic Chemistry: Synthesis, Applications and Future Directions P.V. Ramachandran ACS Symposium Series 746 2000 American Chemical Society Washington, DC 1
20. For a review focusing on marketed pharmaceuticals, see: A.J. Elliott Chemistry of Organic Fluorine Compounds II: A Critical Review M. Hudlicky A.E. Pavlath ACS Monograph 187 1995 American Chemical Society Washington, DC 1119
21. D. O’Hagan, and H.S. Rzepa J. Chem. Soc., Chem. Commun. 1997 645
22. M.H. Lim, H.O. Kim, H.R. Moon, M.H. Chun, and L.S. Jeong Org. Lett. 4 2002 529
23. Y.M. Ming Pu, D.S. Torok, H.J. Ziffer, X.Q. Pan, and S.R. Meshnick J. Med. Chem. 38 1995 4120
24. A.G. Mayers, J.K. Barbay, and B. Zhong J. Am. Chem. Soc. 123 2001 7207
25. A. Kamal, E. Laxman, and M. Arifuddin Tetrahedron Lett. 41 2000 7743
26. A. Kamal, G.S.K. Reddy, and S. Raghavan Bioorg. Med. Chem. Lett. 13 2001 387
27. A. Kamal, P.S.M.M. Reddy, and D.R. Reddy Tetrahedron Lett. 43 2002 6629
28. A. Kamal, G. Ramesh, N. Laxman, P. Ramulu, O. Srinivas, K. Neelima, A.K. Kondapi, V.B. Sreenu, and H.M. Nagarajaram J. Med. Chem. 45 2002 4679
29. A. Kamal, B.S.N. Reddy, G.S.K. Reddy, and G. Ramesh Bioorg. Med. Chem. Lett. 12 2002 1933
30. A. Kamal, G. Ramesh, P. Ramulu, O. Srinivas, T. Rehana, and G. Sheelu Bioorg. Med. Chem. Lett. 13 2003 3451
31. A. Kamal, P. Ramulu, O. Srinivas, and G. Ramesh Bioorg. Med. Chem. Lett. 13 2003 3517
32. A. Kamal, O. Srinivas, P. Ramulu, G. Ramesh, and P.P. Kumar Bioorg. Med. Chem. Lett. 13 2003 3577
33. A. Kamal, P.S.M.M. Reddy, and D.R. Reddy Bioorg. Med. Chem. Lett. 14 2004 2669
34. L. Dc Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 3 2001 3041
35. W.B. Motherwell, M.J. Tozer, and B.C. Ross Chem. Commun. 1989 1437
36. J.S. Houlton, W.B. Motherwell, B.C. Ross, M.J. Tozer, D.J. Williams, and A.M.Z. Slawin Tetrahedron 49 1993 8087
37. X.-L. Qiu, and F.-L. Qing J. Org. Chem. 67 2002 7162
38. D.E. Thurston, V.S. Murty, D.R. Langley, and G.B. Jones Synthesis 1990 81
39. +
40. A. Kamal, P.S.M.M. Reddy, and D.R. Reddy Tetrahedron Lett. 44 2003 2857