Recent advances on antitumor-active benzo[c]phenanthridine alkaloids

Heterocycles

Volumn 50, Issue 1, 1999, Pages 627-639

  Ishikawa, Tsutomu ^a   Ishii, Hisashi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; PHENANTHRIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; CHEMICAL BOND; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NITROSATION; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0032815993     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-98-SR(H)9     Document Type: Review

References (54)

1. Unfortunately Prof. Hisashi Ishii was died on 24th April, 1998 during preparation of this review.
2. a) I. Ninomiya and T. Naito, 'Recent Developments in the Chemistry of Natural Carbon Compounds', Vol 10, ed. by R. Bognar and Cs. Szantay, Akademiai Kiado, Budapest, 1984, pp. 11-90; V. Simanek, 'The Alkaloids', Vol. 26, ed. by A. Brossi, Academic Press. Inc., New York, 1985, pp. 185-240; J. Dostal and M. Potacek, Coll. Czech. Chem. Commun., 1990, 55, 2840.
3. a) I. Ninomiya and T. Naito, 'Recent Developments in the Chemistry of Natural Carbon Compounds', Vol 10, ed. by R. Bognar and Cs. Szantay, Akademiai Kiado, Budapest, 1984, pp. 11-90; V. Simanek, 'The Alkaloids', Vol. 26, ed. by A. Brossi, Academic Press. Inc., New York, 1985, pp. 185-240; J. Dostal and M. Potacek, Coll. Czech. Chem. Commun., 1990, 55, 2840.
4. a) I. Ninomiya and T. Naito, 'Recent Developments in the Chemistry of Natural Carbon Compounds', Vol 10, ed. by R. Bognar and Cs. Szantay, Akademiai Kiado, Budapest, 1984, pp. 11-90; V. Simanek, 'The Alkaloids', Vol. 26, ed. by A. Brossi, Academic Press. Inc., New York, 1985, pp. 185-240; J. Dostal and M. Potacek, Coll. Czech. Chem. Commun., 1990, 55, 2840.
5. b) M. Hanaoka, 'The Alkaloids', Vol. 33, ed. by A. Brossi, Academic Press. Inc., New York, 1988, pp. 141-233.
6. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
7. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
8. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
9. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
10. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
11. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
12. (c) K. W. Bentley, Natural Product Reports, 1991, 8, 350-352; 1992, 9, 374-375; 1993, 10, 457-458; 1994, 11, 562-563; 1995, 12, 427; 1996, 13, 135-136; 1997, 14, 395-396.
13. Q. M. Probst, Ann., 1839, 29, 120.
14. W. M. Messmer, M. Tin-Wa, H. H. S. Fong, C. Bevelle, N. R. Farnsworth, D. J. Abraham, and J. Trojanek, J. Pharm. Sci., 1972, 61, 1858; M. Tin-Wa, C. L. Bell, C. Bevelle, H. H. S. Fong, and N. R. Farnsworth, ibid., 1974, 63, 1476; R. K.-Y. Zee-Cheng and C. C. Cheng, J. Med. Chem., 1975, 18, 66; F. R. Stermitz, J. P. Gillespie, L. G. Amoros, R. Romero, and T. A. Stermitz, ibid., 1975, 18, 708.
15. W. M. Messmer, M. Tin-Wa, H. H. S. Fong, C. Bevelle, N. R. Farnsworth, D. J. Abraham, and J. Trojanek, J. Pharm. Sci., 1972, 61, 1858; M. Tin-Wa, C. L. Bell, C. Bevelle, H. H. S. Fong, and N. R. Farnsworth, ibid., 1974, 63, 1476; R. K.-Y. Zee-Cheng and C. C. Cheng, J. Med. Chem., 1975, 18, 66; F. R. Stermitz, J. P. Gillespie, L. G. Amoros, R. Romero, and T. A. Stermitz, ibid., 1975, 18, 708.
16. W. M. Messmer, M. Tin-Wa, H. H. S. Fong, C. Bevelle, N. R. Farnsworth, D. J. Abraham, and J. Trojanek, J. Pharm. Sci., 1972, 61, 1858; M. Tin-Wa, C. L. Bell, C. Bevelle, H. H. S. Fong, and N. R. Farnsworth, ibid., 1974, 63, 1476; R. K.-Y. Zee-Cheng and C. C. Cheng, J. Med. Chem., 1975, 18, 66; F. R. Stermitz, J. P. Gillespie, L. G. Amoros, R. Romero, and T. A. Stermitz, ibid., 1975, 18, 708.
17. W. M. Messmer, M. Tin-Wa, H. H. S. Fong, C. Bevelle, N. R. Farnsworth, D. J. Abraham, and J. Trojanek, J. Pharm. Sci., 1972, 61, 1858; M. Tin-Wa, C. L. Bell, C. Bevelle, H. H. S. Fong, and N. R. Farnsworth, ibid., 1974, 63, 1476; R. K.-Y. Zee-Cheng and C. C. Cheng, J. Med. Chem., 1975, 18, 66; F. R. Stermitz, J. P. Gillespie, L. G. Amoros, R. Romero, and T. A. Stermitz, ibid., 1975, 18, 708.
18. M. Suzuki, T. Nakanishi, O. Kogawa, K. Ishikawa, F. Kobayashi, and H. Ekimoto, Eur. Pat. Appl. EP 487, 930, 1992 (Chem. Abstr., 1992, 117, P191, 706b); F. Kobayashi, H. Yokumoto, M. Suzuki, and M. Tsubuki, Jpn. Kokai Tokkyo Koho, JP 04, 364, 128, 1992 (Chem. Abstr., 1993, 118, P219,845t); M. Fukuda, M. Inomata, K. Nishino, K. Fukuoka, F. Kanzawa, H. Arioka, T. Ishida, H. Fukumoto, H. Kurokawa, M. Oka, and N. Saijo, Jpn. J. Cancer Res., 1996, 87, 1086.
19. M. Suzuki, T. Nakanishi, O. Kogawa, K. Ishikawa, F. Kobayashi, and H. Ekimoto, Eur. Pat. Appl. EP 487, 930, 1992 (Chem. Abstr., 1992, 117, P191, 706b); F. Kobayashi, H. Yokumoto, M. Suzuki, and M. Tsubuki, Jpn. Kokai Tokkyo Koho, JP 04, 364, 128, 1992 (Chem. Abstr., 1993, 118, P219,845t); M. Fukuda, M. Inomata, K. Nishino, K. Fukuoka, F. Kanzawa, H. Arioka, T. Ishida, H. Fukumoto, H. Kurokawa, M. Oka, and N. Saijo, Jpn. J. Cancer Res., 1996, 87, 1086.
20. M. Suzuki, T. Nakanishi, O. Kogawa, K. Ishikawa, F. Kobayashi, and H. Ekimoto, Eur. Pat. Appl. EP 487, 930, 1992 (Chem. Abstr., 1992, 117, P191, 706b); F. Kobayashi, H. Yokumoto, M. Suzuki, and M. Tsubuki, Jpn. Kokai Tokkyo Koho, JP 04, 364, 128, 1992 (Chem. Abstr., 1993, 118, P219,845t); M. Fukuda, M. Inomata, K. Nishino, K. Fukuoka, F. Kanzawa, H. Arioka, T. Ishida, H. Fukumoto, H. Kurokawa, M. Oka, and N. Saijo, Jpn. J. Cancer Res., 1996, 87, 1086.
21. K. Iwasa, 'The Alkaloids', Vol. 46, ed. by G. A. Cordell, Academic Press. Inc., New York, 1995, pp. 273-346.
22. T. Richardson, R. Robinson, and E. Seijo, J. Chem. Soc., 1937, 835; A. S. Bailey and R. Robinson, ibid., 1950, 1375.
23. T. Richardson, R. Robinson, and E. Seijo, J. Chem. Soc., 1937, 835; A. S. Bailey and R. Robinson, ibid., 1950, 1375.
24. H. Ishii, Y.-I. Ichikawa, E. Kawanabe, M. Ishikawa, T. Ishikawa, K. Kuretani, M. Inomata, and A. Hoshi, Chem. Pharm. Bull., 1985, 33, 4139.
25. T. Ishikawa, T. Saito, and H. Ishii, Tetrahedron, 1995, 51, 8447.
26. T. Ishikawa, T. Watanabe, H. Tanigawa, T. Saito, K.-I. Kotake, Y. Ohashi, and H. Ishii, J. Org. Chem., 1996, 61, 1774.
27. T. Ishikawa, T. Saito, S. Noguchi, H. Ishii, S. Ito, and T. Hata, Tetrahedron Lett., 1995, 36, 2795.
28. T. Ishikawa, K. Simooka, S. Noguchi, A. Ishikawa, E. Yamazaki, T. Narioka, T. Harayama, and H. Ishii, unpublished results.
29. N. Sotomayor, E. Dominguez, and E. Lete, Tetrahedron Lett, 1994, 35, 2973; idem, J. Org. Chem., 1996, 61, 4062.
30. N. Sotomayor, E. Dominguez, and E. Lete, Tetrahedron Lett, 1994, 35, 2973; idem, J. Org. Chem., 1996, 61, 4062.
31. I. Iwai and J. Ide, Chem. Pharm. Bull., 1962, 10, 926; 1963, 11, 1042.
32. I. Iwai and J. Ide, Chem. Pharm. Bull., 1962, 10, 926; 1963, 11, 1042.
33. H. Ishii, T. Ishikawa, S. Takeda, S. Ueki, and M. Suzuki, Chem. Pharm. Bull., 1992, 40, 1148.
34. H. Ishii, T. Ishikawa, S. Takeda, M. Suzuki, and T. Harayama, Chem. Pharm. Bull., 1992, 40, 2002.
35. T. Ishikawa, A. Takami, M. Abe, I.-S. Chen, T. Harayama, and H. Ishii, Chem. Pharm. Bull., 1995, 43, 766.
36. A. Couture, H. Cornet, and P. Grandclaudon, Tetrahedron Lett., 1993, 34, 8097.
37. T. Harayama, T. Akiyama, and K. Kawano, Chem. Pharm. Bull., 1996, 44, 1634; T. Harayama, T. Akiyama, and Y. Nakano, ibid., 1997, 45, 1723.
38. T. Harayama, T. Akiyama, and K. Kawano, Chem. Pharm. Bull., 1996, 44, 1634; T. Harayama, T. Akiyama, and Y. Nakano, ibid., 1997, 45, 1723.
39. a) M. Hanaoka, W. J. Cho, Y. Sugiura, and C. Mukai, Chem. Pharm. Bull., 1991, 39, 242;
40. b) T. Minami, A. Nishimoto, and M. Hanaoka, Tetrahedron Lett., 1995, 36, 9505.
41. R. Beugelmans and M. Bois-Choussy, Tetrahedron, 1992, 48, 8285.
42. M. A. Lynch, O. Duval, P. Pochet, and R. D. Waigh, Bull. Soc. Chim. Fr., 1994, 131, 718.
43. D. Seraphin, M. A. Lynch, and O. Duval, Tetrahedron Lett., 1995, 36, 5731.
44. G. Martin, E. Guitian, L. Castedo, and J. M. Saa, J. Org. Chem., 1992, 57, 5907; D. Perez, E. Guitian, and L. Castedo, ibid., 1992, 57, 5911.
45. G. Martin, E. Guitian, L. Castedo, and J. M. Saa, J. Org. Chem., 1992, 57, 5907; D. Perez, E. Guitian, and L. Castedo, ibid., 1992, 57, 5911.
46. J. H. Rigby and D. D. Holsworth, Tetrahedron Lett., 1991, 32, 5757.
47. Y. L. Janin, A. Croisy, J.-F. Riou, and E. Bisagni, J. Med. Chem., 1993, 36, 3686.
48. M. Suffness and G. A. Cordell, 'The Alkaloids', Vol. 25, ed. by A. Brossi, Academic Press. Inc., New York, 1985, pp. 178-187.
49. S.-D. Fang, L.-K. Wang, and S. M. Hecht, J. Org. Chem., 1993, 58, 5025.
50. J. M. Herbert, J. M. Augereau, J. Gleye, and J. P. Maffrand, Biochem. Biophys. Res. Commun., 1990, 172, 993.
51. B. H. Wang, Z. X. Lu, and G. M. Polya, Planta Med., 1997, 63, 494.
52. T. Schmeller, B. Latz-Bruning, and M. Wink, Phytochemistry, 1997, 44, 257.
53. W.-J. Cho, S.-J. Yoo, B.-H. Chung, S.-H. Whang, S.-K. Kim, B.-H. Kang, and C.-O. Lee, Arch. Pharm. Res., 1996, 19, 321.
54. W.-J. Cho, M.-J. Park, B.-H. Chung, and C.-O. Lee, Bioorg. Med. Chem. Lett., 1998, 8, 41.