Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid

Journal of Natural Products

Volumn 62, Issue 6, 1999, Pages 864-867

  Nakanishi, Takeshi ^a   Suzuki, Masanobu ^a   Saimoto, Atsuya ^a   Kabasawa, Takashi ^a  

^a NIPPON KAYAKU CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXY 2,3 METHYLENEDIOXY 5 METHYL 8 METHOXYBENZO PHENANTHRIDINIUM HYDROGENSULFATE; AMPHOLYTE; CHELERYTHRINE; FAGARIDINE; FAGARONINE; PHENANTHRIDINE DERIVATIVE; SANGUINARINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HELA CELL; HUMAN; HUMAN CELL; LEUKEMIA P 388 CELL; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HELA CELLS; HUMANS; LEUKEMIA P388; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED STRAINS; NEOPLASM TRANSPLANTATION; PHENANTHRIDINES; TUMOR CELLS, CULTURED;

EID: 0033059590     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np990005d     Document Type: Article

References (28)

1. Šimánek, V. The Alkaloids; Academic: New York, 1985; Vol. 26, pp 185-240.
2. Wall, M. E.; Wani, M. C.; Taylor, H. L. Abstract of Papers, 162nd National Meeting of American Chemical Society, Washington, D. C. 1971; American Chemical Society: Washington, DC, 1971; MEDI 34.
3. Messmer, W. M.; Tin-Wa, M.; Fong, H. H. S.; Bevelle, C.; Farnsworth, N. R.; Abraham, D. J.; Trojánek, J. J. Pharm. Sci. 1972, 61, 1858-1859.
4. Cordell, G. A.; Farnsworth, N. R. Heterocycles 1976, 4, 393-427.
5. Phillips, S. D.; Castle, R. N. J. Heterocyclic Chem. 1981, 18, 223-232.
6. Suffness, M.; Cordell, G. A. The Alkaloids; Academic: New York, 1985; Vol. 25, pp 178-189.
7. Stermitz, F. R.; Gillespie, J. P.; Amoros, L. G.; Romero, R.; Stermitz, T. A.; Larson, K. A.; Earl, S.; Ogg, J. E. J. Med. Chem. 1975, 18, 708-713.
8. Zee-Cheng, R. K.-Y.; Cheng, C. C. J. Med. Chem. 1975, 18, 66-71.
9. Cushman, M.; Mohan, P.; Smith, E. C. R. J. Med. Chem. 1984, 27, 544-547.
10. Cushman, M.; Mohan, P. J. Med. Chem. 1985, 28, 1031-1036.
11. Ishii, H.; Ichikawa, Y.; Kawanabe, E.; Ishikawa, M.; Ishikawa T.; Kuretani, K.; Inomata, M.; Hoshi, A. Chem. Pharm. Bull. 1985, 33, 4139-4151.
12. Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686-3692.
13. Arisawa, M.; Pezzuto, J. M.; Bevelle, C.; Cordell, G. A. J. Nat. Prod. 1984, 47, 453-458.
14. Hanaoka, M.; Ekimoto, H.; Kobayashi, M. F.; Irie, Y.; Takahashi, K. Chem. Abstr. 1989, 116, 718d.
15. Topoisomerase activity of 3 was reported in the following: (a) Fukuda, M.; Inomata, M.; Nishio, K.; Fukuoka, K.; Kanzawa, F.; Arioka, H.; Ishida, T.; Fukumoto, H.; Kurokawa, H.; Oka, M.; Saijo, N. Jpn. J. Cancer Res. 1996, 87, 1086-1091.
16. (b) Kabasawa, T.; Kobayashi, F.; Ekimoto, H.; Suzuki, M.; Hanaoka, M. Proc. Am. Assoc. Cancer Res. 1996, 37, 427.
17. Topoisomerase activity of other benzo[c]phenanthridine alkaloids (1, 4, 5) was reported in the following: (a) Fang, S.-D.; Wang, L.-K.; Hecht, S. M. J. Org. Chem. 1993, 58, 5025-5027.
18. (b) Makhey, D.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Med. Chem. Res. 1995, 5, 1-12.
19. Kanzawa, F.; Nishio, K.; Ishida, T.; Fukuda, M.; Kurokawa, H.; Fukumoto, H.; Nomoto, Y.; Fukuoka, K.; Bojanowski, K.; Saijo, N. Br. J. Cancer 1997, 76, 571-581.
20. Lu, H.; Rutan, S. C. Anal. Chem. 1996, 68, 1381-1386.
21. Šimánek, V.; Preininger, V. Heterocycles 1977, 6, 475-497.
22. Kessar, S. V.; Gupta, Y. P.; Balakrishnan, P.; Sawal, K. K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708-1713.
23. Stermitz, F. R.; Larson, K. A.; Kim, D. K. J. Med. Chem. 1973, 16, 939-940.
24. Caolo, M. A.; Stermitz, F. R. Heterocycles 1979, 12, 11-15.
25. Walterová, D.; Preininger, V.; Grambal, F.; Šimánek, V.; Šantavý, F. Heterocycles 1980, 14, 597-600.
26. Zee-Cheng, R. K.-Y.; Yan, S.-J.; Cheng, C. C. J. Med. Chem. 1978, 21, 199-203.
27. Nakanishi, T.; Suzuki, M.; Mashiba, A.; Ishikawa, K.; Yokotsuka, T. J. Org. Chem. 1998, 63, 4235-4239.
28. Nakanishi, T.; Suzuki, M. J. Nat. Prod. 1998, 61, 1263-1267.