Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine

Chemical Communications

Volumn 14, Issue , 2003, Pages 1688-1689

  Kang, Gyoung Dong ^a   Howard, Philip W ^a   Thurston, David E ^a  

^a IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; BENZODIAZEPINE DERIVATIVE; PYRROLOBENZODIAZEPINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037963752     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303274d     Document Type: Article

References (16)

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3. D. E. Thurston and D. S. Bose, Chem. Rev., 1994, 94, 433.
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6. S. J. Gregson, P. W. Howard, J. A. Hartley, N. A. Brooks, L. J. Adams, T. C. Jenkins, L. R. Kelland and D. E. Thurston, J. Med. Chem., 2001, 44, 737.
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8. The simple C1-C2 unsaturated C2-unsubstituted parent compound is known in the literature (see ref. 16) but the synthetic route used is restricted to this parent.
9. S. J. Gregson, P. W. Howard, K. E. Corcoran, S. Barcella, M. M. Yasin, A. A. Hurst, T. C. Jenkins, L. R. Kelland and D. E. Thurston, Bioorg. Med. Chem. Lett., 2000, 10, 1845.
10. A. DeMico, R. Margarita, L. Parlanti, A. Vescovi and G. Piancatelli, J. Org. Chem., 1997, 62, 6974.
11. K. Ritter, Synthesis (Stuttgart), 1993, 735.
12. The 2,3-unsaturated product 7 exhibited spin systems for H-1 and H-1′ at 2.9 and 3.1 ppm, and an H-3 signal was observed at 6.0 ppm. In contrast, the 1,2-unsaturated compound 8 revealed two 3-H protons at 4.1 and a H-1 alkenic signal at 5.85 ppm.
13. -1.
14. Exposure of 14 to heat during work-up should be avoided as this can provoke C-ring aromatization.
15. In contrast the spectrum of 3 clearly shows two distinct spin systems for H1 and H1′ at 3.4 and 3.6 ppm, and the diagnostic enamide 3-H at 7.4 ppm.
16. L. H. Hurley, T. Reck, D. E. Thurston, D. R. Langley, K. G. Holden, R. P. Hertzberg, J. R. E. Hoover, G. Gallagher, L. F. Faucette, S. M. Mong and R. K. Johnson, Chem. Res. Toxicol., 1988, 1, 258.