Synthesis and antitumor activity of canthin-5,6-dione derivatives

Heterocycles

Volumn 51, Issue 2, 1999, Pages 315-323

  Koike, Kazuo ^a   Yoshino, Hiroshi ^a   Nikaido, Tamotsu ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE DERIVATIVE; CANTHIN 5,6 DIONE; CANTHIN 6 ONE DERIVATIVE; CISPLATIN; OXALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL REACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA P 388 CELL; LUNG CARCINOMA; MOUSE; NONHUMAN; X RAY CRYSTALLOGRAPHY;

EID: 0033080513     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-8394     Document Type: Article

References (16)

1. T. Ohmoto and K. Koike, Chem. Pharm. Bull., 1982, 30, 1204.
2. T. Ohmoto and K. Koike, Chem. Pharm. Bull., 1985, 33, 3847.
3. T. Ohmoto and K. Koike, Chem. Pharm. Bull., 1985, 33, 4901.
4. K. Mitsunaga, K. Koike, T. Tanaka, Y. Ohkawa, Y. Kobayashi, T. Sawaguchi, and T. Ohmoto, Phytochemistry, 1994, 35, 799.
5. T. Ohmoto and K. Koike, Chem. Pharm. Bull., 1984, 32, 3579. 4-Methoxy-5-hydroxycanthin-6-one (nigakinone,13): UV λ max (MeOH) nm (log ε): 246 (4.60), 262 (sh, 4.50), 286 (4.25), 340 (4.01), 350 (4.00). UV λ max (MeOH+NaOH) nm (log ε): 254 (4.53), 286 (4.44), 318 (3.95), 4.20 (4.19). UV λ max (MeOH+HCl) nm (log ε): 248 (3.65), 322 (4.00), 360 (4.25), 274 (4.25), 234 (3.94). (equation presented)
6. W. A. Jacobs and L. C. Craig, J. Biol. Chem., 1936, 113, 759; A. Brossi, A. Focella, and S. I Teitel, J. Med. Chem., 1973, 16, 418; J. M. Bobbit and J. P. Willis, J. Org. Chem., 1980, 45, 1978; H. R. Synder, C. H. Hansch, L. Katz, S. M. Parmerter, and E. C. Spaeth, J. Am. Chem. Soc., 1948, 70, 219.
7. W. A. Jacobs and L. C. Craig, J. Biol. Chem., 1936, 113, 759; A. Brossi, A. Focella, and S. I Teitel, J. Med. Chem., 1973, 16, 418; J. M. Bobbit and J. P. Willis, J. Org. Chem., 1980, 45, 1978; H. R. Synder, C. H. Hansch, L. Katz, S. M. Parmerter, and E. C. Spaeth, J. Am. Chem. Soc., 1948, 70, 219.
8. W. A. Jacobs and L. C. Craig, J. Biol. Chem., 1936, 113, 759; A. Brossi, A. Focella, and S. I Teitel, J. Med. Chem., 1973, 16, 418; J. M. Bobbit and J. P. Willis, J. Org. Chem., 1980, 45, 1978; H. R. Synder, C. H. Hansch, L. Katz, S. M. Parmerter, and E. C. Spaeth, J. Am. Chem. Soc., 1948, 70, 219.
9. W. A. Jacobs and L. C. Craig, J. Biol. Chem., 1936, 113, 759; A. Brossi, A. Focella, and S. I Teitel, J. Med. Chem., 1973, 16, 418; J. M. Bobbit and J. P. Willis, J. Org. Chem., 1980, 45, 1978; H. R. Synder, C. H. Hansch, L. Katz, S. M. Parmerter, and E. C. Spaeth, J. Am. Chem. Soc., 1948, 70, 219.
10. M. Cain, R. Mantei, and J. M. Cook, J. Org. Chem., 1982, 47, 4933.
11. K. Wakabayashi, T. Yamamoto, K. Tsuji, H. Zenda, and T. Kosuge, Yakugaku Zasshi, 1978, 98, 898; M. R. Prinsep, J. W. Blunt, and M. H. G. Munro, J. Nat. Prod., 1991, 54, 1068.
12. K. Wakabayashi, T. Yamamoto, K. Tsuji, H. Zenda, and T. Kosuge, Yakugaku Zasshi, 1978, 98, 898; M. R. Prinsep, J. W. Blunt, and M. H. G. Munro, J. Nat. Prod., 1991, 54, 1068.
13. T. Debaerdemaeker, G. Germain, P. Main, L. S. Refaat, C. Tate, and M. M. Woolfson, Computer programs for the automatic solution of crystal structures for X-Ray diffraction data 1988, University of York, U. K.
14. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israe, and J. M. M. Smits. The DIRDIF94 program system 1994, Technical Report of the Crystallography Laboratory., University of Nijmegen, The Netherlands.
15. M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, and D. Viterbo, J. Appl. Cryst., 1989, 22, 389.
16. I. Mitsui, E. Kumazawa, Y. Hirota, M. Aonuma, M. Sugimori, S. Ohsuki, K. Uoto, and A. Ejima, Jpn. J. Cancer Res., 1995, 86, 776.