The Organic Chemistry of the Pyrrolo[1,2-a]benzimidazole Antitumor Agents. An Example of Rational Drug Design

Synlett

Volumn 1996, Issue 4, 1996, Pages 297-309

  Skibo, Edward B ^a,b,c,d   Islam, Imadul ^a,e   Schulz, William G ^a   Zhou, Ru ^a,d   Bess, Laura ^a   Boruah, Romesh ^a,f  

^a ARIZONA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Synaptic Pharmaceutical Corporation ^*

^e H LUNDBECK A S   (Denmark)

^f REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542530183     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5399     Document Type: Article

References (48)

1. Skibo, E. B.; Islam, I. U.S. Patent 5,015,742, 1991. Chem. Abstr. 1992, 115, 183297.
2. Skibo, E. B.; Islam, I.; Alberts, D. S. U.S. Patent 5,246,955, 1993. Chem. Abstr. 1993, 116, 21048a.
3. Skibo, E. B.; Schulz, W. G. J. Med. Chem. 1993, 36, 3050.
4. Skibo, E. B.; Islam, I.; Heileman, M. J.; Schulz, W. G. J. Med. Chem. 1994, 37, 78.
5. Boruah, R. C.; Skibo, E. B. J. Med. Chem. 1994, 37, 1625.
6. Sigman, D. S. Biochemistry 1990, 29, 9097.
7. (a) Jubian, V.; Dixon, R. P.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 1120.
8. (b) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1993, 115, 9337.
9. (c) Smith, J.; Ariga, K.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 362.
10. (d) Chin, J. Acc. Chem. Res. 1991, 24, 145.
11. Schulz, W. G.; Islam, I.; Skibo, E. B. J. Med. Chem. 1995, 38, 109.
12. Islam, I.; Skibo, E. B. J. Org. Chem. 1990, 55, 3195.
13. Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl. Chem. 1972, 14, 211.
14. Grantham, R. K.; Meth-Cohn, O. J. Chem. Soc., C 1969, 70.
15. The chemistry of benzimidazole N-oxides is discussed in the following reports: (a) Takahashi, S.; Kanō, H. Chem. Pharm. Bull. 1966, 14, 1219. (b) Takahashi, S.; Kanō, H. Chem. Pharm. Bull. 1964, 12, 783.
16. The chemistry of benzimidazole N-oxides is discussed in the following reports: (a) Takahashi, S.; Kanō, H. Chem. Pharm. Bull. 1966, 14, 1219. (b) Takahashi, S.; Kanō, H. Chem. Pharm. Bull. 1964, 12, 783.
17. Islam, I.; Skibo, E. B.; Dorr, R. T.; Alberts, D. S. J. Med. Chem. 1991, 34, 2954.
18. (a) Elson, L. A., Gibson, C. S.; Johnson, J. D. J. Chem. Soc. 1929, 2735.
19. (b) Blackbarn, W.; Danzig, M.; Hubinger, H.; Soisson, D.; Schultz, H. P. J. Org. Chem. 1961, 26, 2805.
20. Nair, M. D.; Adams, R. J. Am. Chem. Soc. 1961, 83, 3518.
21. Philips, M. A. J. Chem. Soc. 1928, 2393.
22. Ringdahl, B.; Craig, J. C. Acta Chemica Scand. B 1980, 34, 3.
23. Bodansky, M.; Bodansky, A. The Practice of Peptide Synthesis; Springer-Verlag: Berlin; 1984, p. 66.
24. (a) E. Fremy Ann. Chim. Phys., 1845, 15, 408.
25. (b) Zimmer, H.; Lankin, D. C.; Horgan, S. W. Chem. Rev. 1971, 71, 229.
26. (a) Teuber, H.-J.; Rau, W. Chem. Ber. 1953, 86, 1036.
27. (b) Teuber, H.-J.; Jellinck, G. Chem. Ber. 1954, 87, 1841.
28. (c) Teuber, H.-J.; Hasselbach, M. Chem. Ber. 1959, 92, 674.
29. For examples of reductive addition reactions see Finley, K. T. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley: New York, 1974, Part 2, Chapter 17; pp 880-947.
30. Reeves, W. A.; Drake, Jr., G. L.; Hoffpauir, C. L. J. Am. Chem. Soc. 1951, 73, 3522.
31. (a) Horner, L.; Sturm, K. Chem. Ber. 1955, 88, 329.
32. (b) Helissey, P.; Parrot-Lopez, H.; Renault, J.; Cros, S. Chem. Pharm. Bull. 1987, 35, 3547.
33. Skibo, E. B.; Gilchrist, J. H. J. Org. Chem. 1988, 53, 4209.
34. Doroshow, J. H. Cancer Res. 1983, 43, 460.
35. Dermer, O. C.; Ham, G. E. Ethyleneimines and Other Aziridines; Academic Press: New York, NY, 1969; pp 205-293.
36. (a) Hartley, J. A.; Berardini, M.; Ponti, M.; Gibson, N. W.; Thompson, A. S.; Thurston, D. E.; Hoey, B. M.; Butler, J. Biochemistry 1991, 30, 11719.
37. (b) Lee, C.-S.; Hartley, J. A.; Berardini, M. D.; Butler, J.; Siegel, D.; Ross, D.; Gibson, N. W. Biochemistry 1992, 31, 3019.
38. (c) Berardini, M. D.; Souhami, R. L.; Lee, C.-S.; Gibson, N. W.; Butler, J.; Hartley, J. A. Biochemistry 1993, 32, 3306.
39. Franck, R. W.; Tomasz, M. In The Chemistry of Antitumor Agents, Wilman, D. E. V., Ed.; Blackie and Sons, Ltd.: Glasgow, Scotland, 1990; p 379.
40. For a recent theoretical study and reference list see Norberg, J.; Nilsson, L. Biophysical J. 1994, 67, 812.
41. (a) Fu, J. M.; Schroeder, S. A.; Jones, C. R.; Santini, R.; Gorenstein, D. G. J. Mag. Res. 1988, 77, 577.
42. (b) Jones, C. R.; Schroeder, S. A.; Gorenstein, D. G. J. Mag. Res. 1988, 80, 370.
43. Pearson, R. G. Hard and Soft Acids and Bases; Dowden, Hutchinson and Ross: Stroudsburg, PA, 1981.
44. Hemminki, A.; Väyrynen, T.; Hemminki, K. Chem. Bio. Interact. 1994, 15, 51.
45. Yates, J. M.; Fennell, T. R.; Turner, M. J.; Recio, L.; Summer, S. C. J. Carcinogenesis 1994, 15, 277.
46. (a) Bannon, P.; Verly, W. Eur. J. Biochem. 1972, 31, 103.
47. (b) Conrad, J.; Müller, N.; Eisenbrand, G. Chem. Biol. Interactions 1986, 60, 57.
48. Maxam, A. M.; Gilbert, W. Methods Enzymol. 1980, 69, 499.