Synthesis of NK109, an anticancer benzo[c]phenanthridine alkaloid

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4235-4239

  Nakanishi, Takeshi ^a   Suzuki, Masanobu ^a   Mashiba, Akihiro ^a   Ishikawa, Keizou ^a   Yokotsuka, Takashi ^a  

^a NIPPON KAYAKU CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXY 8 METHOXY 5 METHYL 2,3 METHYLENEDIOXYBENZO[C]PHENANTHRIDINIUM HYDROGENSULFATE DIHYDRATE; ALKALOID; ANTINEOPLASTIC AGENT; BENZALDEHYDE; BENZO[C]PHENANTHRIDINE DERIVATIVE; BENZYLAMINE; BUTYRONITRILE; FAGARIDINE; NAPHTHYL GROUP; NAPHTHYLAMINE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032568996     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9718758     Document Type: Article

References (56)

1. Šimánek, V. The Alkaloids, Academic: New York, 1985; Vol. 26, p 185.
2. (a) Arthur, H. R.; Hui, W. H.; Ng, Y. L. Chem. & Ind. (London) 1958, 1514.
3. (b) Wall, M. E.; Wani, M. C.; Taylor, H. L. Abstracts of Papers, 162nd National Meeting of American Chemical Society; American Chemical Society: Washington, DC, 1971; MEDI34.
4. (c) 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.
5. (d) Gadamer, J.; Stickel, A. Arch. Pharm. 1924, 262, 452.
6. (e) Gadamer, J. Arch. Pharm. 1920, 258, 148.
7. (a) Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 223.
8. (b) Suffness, M.; Cordell, G. A. The Alkaloids; Academic: New York, 1985; Vol. 25, p 178.
9. (a) Stermitz, F. R.; Larson, K. A.; Kim, D. K. J. Med. Chem. 1973, 16, 939.
10. (b) Caolo, M. A.; Stermitz, F. R. Heterocycles 1979, 12, 11.
11. (a) Zee-Cheng, R. K.-Y.; Cheng, C. C. J. Med. Chem. 1975, 18, 66.
12. (b) Stermitz, F. R.; Gillespie, J. P.; Amoros, L. G.; Romero, R.; Stermitz, T. A. J. Med. Chem. 1975, 18, 708.
13. (c) Zee-Cheng, R. K.-Y.; Yan, S.-J.; Cheng, C. C. J. Med. Chem. 1978, 21, 199.
14. (d) Cushman, M.; Mohan, P.; Smith, E. C. R. J. Med. Chem. 1984, 27, 544.
15. (e) Cushman, M.; Mohan, P. J. Med. Chem. 1985, 28, 1031.
16. (f) Ishii, H.; Ichikawa, Y.; Kawanabe, E.; Ishikawa, M.; Ishikawa, T.; Kuretani, K.; Inomata, M.; Hoshi, A. Chem. Pharm. Bull. 1985, 33, 4139.
17. (a) Pezzuto, J. M.; Antosiak, S. K.; Messmer, W. M.; Slaytor, M. B.; Honig, G. R. Chem.-Biol. Interact. 1983, 43, 323.
18. (b) Kusumoto, I. T.; Hattori, M.; Miyaichi, Y.; Tomimori, T.; Hanaoka, M.; Namba, T. Shoyakugaku Zasshi 1991, 45, 240.
19. (c) Martín, G.; Guitiín, E.; Castedo, L.; Saa, J. M. J. Org. Chem. 1992, 57, 5907.
20. (d) Larsen, A. K.; Grondard, L.; Couprie, J.; Desoize, B.; Comoe, L.; Jardillier, J.-C.; Riou, J.-F. Biochem. Pharmacol. 1993, 46, 1403.
21. (e) Dostál, J.; Táborská, E.; Slavík, J.; Potáček, M.; Hoffmann, E. J. Nat. Prod. 1995, 58, 723.
22. (a) Hanaoka, M. The Alkaloids; Academic: New York, 1988; Vol. 33, p 170.
23. (b) Hanaoka, M.; Mukai, C. Stud. Nat. Prod. Chem. 1994, 14, 769.
24. Hanaoka, M.; Ekimoto, H.; Kobayashi, M. F.; Irie, Y.; Takahashi, K. Chem. Abstr. 1989, 116, 718.
25. Under preparation.
26. 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.
27. Torto, F. G.; Mensah, I. A.; Baxter, I. Phytochemistry 1973, 12, 2315.
28. Submitted for publication.
29. (a) Kametani, T.; Kigasawa, K.; Hiiragi, M.; Kusama, O. J. Heterocycl. Chem. 1973, 10, 31.
30. (b) Zee-Cheng, K.-Y.; Cheng, C. C. J. Heterocycl. Chem. 1973, 10, 85.
31. (c) Ishii, H.; Chen, I.-S.; Ishikawa, T. Chem. Pharm. Bull 1983, 31, 2963.
32. Gillespie, J. P.; Amoros, L. G.; Stermitz, F. R. J. Org. Chem. 1974, 39, 3239.
33. (e) Sainsbury, M.; Dyke, S. F.; Moon, B. J. J. Chem. Soc. C 1970, 1797.
34. (f) Kessar, S. V.; Singh, G.; Balakrishnan, P. Tetrahedron Lett. 1974, 2269.
35. (g) Ninomiya, I.; Naito, T.; Ishii, H.; Ishida, T.; Ueda, M.; Harada, K. J. Chem. Soc., Perkin Trans. 1 1975, 762.
36. (h) Begley, W. J.; Grimshaw, J. J. Chem. Soc., Perkin Trans. 1 1977, 2324.
37. (i) Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 286.
38. (j) Olugbade, T. A.; Waigh, R. D. J. Pharm. Pharmacol. 1981, 33, 81P.
39. (k) Onda, M.; Yamaguchi, H. Chem. Pharm. Bull. 1979, 27, 2076.
40. Kametani, T.; Honda, T.; Inoue, H.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1976, 1221.
41. Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 41, 3361.
42. Castellano, J. A.; Goldmacher, J. E.; Barton, L. A.; Kane, J. S. J. Org. Chem. 1968, 33, 3501.
43. Billman, J. H.; McDowell, J. W. J. Org. Chem. 1961, 26, 1437.
44. (a) Kessar, S. V.; Gopal, R.; Singh, M. Tetrahedron 1973, 29, 167.
45. (b) Kessar, S. V.; Gupta, Y. P.; Balakrishnan, P.; Sawal, K. K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708.
46. (a) Kessar, S. V.; Gupta, Y. P.; Dhingra, K.; Sharma, G. S.; Narula, S. Tetrahedron Lett. 1977, 17, 1459.
47. (b) Šmidrkal, J. Collect. Czech. Chem. Commun. 1984, 49, 1412.
48. Rosa, A. M.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett. 1990, 31, 1881.
49. Schug, J. C.; Viers, J. W.; Seeman, J. I. J. Org. Chem. 1983, 48, 4892.
50. Kiprianov, A. I.; Tolmachev, A. I. Zh. Obshch. Khim. 1959, 29, 2868: Chem. Abstr. 1960, 54, 12126.
51. Kiprianov, A. I.; Tolmachev, A. I. Zh. Obshch. Khim. 1959, 29, 2868: Chem. Abstr. 1960, 54, 12126.
52. Kiprianov, A. I.; Tolmachev, A. I. Zh. Obshch. Khim. 1957, 27, 142: Chem. Abstr. 1957, 57, 12912.
53. Kiprianov, A. I.; Tolmachev, A. I. Zh. Obshch. Khim. 1957, 27, 142: Chem. Abstr. 1957, 57, 12912.
54. (a) Šimánek, V.; Preininger, V. Heterocycles 1977, 6, 475.
55. (b) Bunting, J. W. Adv. Heterocycl. Chem. 1979, 25, 1.
56. As determined by HPLC analysis using the analytical sample as a standard.