Nitrogen and sulfur analogues of the seco-CI alkylating agent: Synthesis and cytotoxicity

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2735-2740

  Tercel, M ^a   Denny, W A ^a   Wilson, W R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; CYTOTOXIC AGENT; INDOLE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0030593869     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00507-0     Document Type: Article

References (23)

1. 1. Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Eng. 1996, 35, 1439, and references cited therein.
2. 2. Boger, D. L.; Yun, W. J. Am. Chem. Soc. 1994, 116, 5523.
3. 3. Wang, Y.; Gupta, R.; Huang, L.; Lown, J. W. J. Med. Chem. 1993, 36, 4172.
4. 4. For examples (a) Fregeau, N. L.; Wang, Y.; Pon, R. T.; Wylie, W. A.; Lown, J. W. J. Am. Chem. Soc. 1995, 117, 8917.
5. (b) Boger, D. L.; Yun, W.; Han, N.; Johnson, D. S. Bioorg. Med. Chem. 1995, 3, 611.
6. (c) Boger, D. L.; Yun, W.; Cai, H.; Han, N. Bioorg. Med. Chem. 1995, 3, 761.
7. (d) Boger, D. L.; Coleman, R. S.; Invergo, B. J.; Sakya, S. M.; Ishizaki, T.; Munk, S. A.; Zarrinmayeh, H.; Kitos, P. A.; Collins Thompson, S. J. Am. Chem. Soc. 1990, 112, 4623.
8. 5. Boger, D. L.; Mésini, P. J. Am. Chem. Soc. 1995 117, 11647.
9. 6. White, R. H.; Parsons, P. G.; Prakash, A. S.; Young, D. J. Bioorg. Med. Chem. Lett. 1995, 5, 1869.
10. 7. Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1990, 112, 8961.
11. 8. Nagamura, S.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Chem. Pharm. Bull. 1995, 43, 1530.
12. 9. (a) Boger, D. L.; Wysocki, R. J., Jr.; Ishizaki, T. J. Am. Chem. Soc. 1990, 112, 5230.
13. (b) Boger, D. L.; Munk, S. A.; Zarrinmayeh, H.; Ishizaki, T.; Haught, J.; Bina, M. Tetrahedron 1991, 47, 2661.
14. 10. See ref. 1 for the influence of C-3 configuration on cytotoxicity and DNA alkylation ability. For the known CI agents the enantiomers are approximately equipotent.
15. 11. Warpehoski, M. A.; Gebhard, I.; Kelly, R. C.; Krueger, W. C.; Li, L. H.; McGovren, J. P.; Prairie, M. D.; Wicnienski, N.; Wierenga, W. J. Med. Chem. 1988, 31, 590.
16. 12. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979.
17. 13. Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315.
18. 3S) C,H,N,Cl] rather than the reported colourless oil.
19. 15. Palmer, B. D.; van Zijl, P.; Denny, W. A.; Wilson, W. R. J. Med. Chem. 1995, 38, 1229.
20. 16. Hoeijmakers, J. H. L.; Bootsma, D. Cancer Cells 1990, 2, 311.
21. 17. Hoy, C. A.; Salazar, E. P.; Thompson, L. H. Mutat. Res. 1984, 130, 321.
22. 18. Fan, J.-Y.; Tercel, M.; Tan, L. K.; Boyd, M.; Denny, W. A., manuscript in preparation.
23. 19. Tannock, I. F.; Rotin, D. Cancer Res. 1989, 49, 4373.