Synthesis and antitumor activity of water-soluble enediyne compounds related to dynemicin A

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 5, 1997, Pages 987-999

  Unno, Ryoichi ^a   Michishita, Hisashi ^a   Inagaki, Hideaki ^a   Suzuki, Yoko ^a   Baba, Yutaka ^a   Jomori, Takahito ^a   Nishikawa, Toshio ^b   Isobe, Minoru ^b  

^a SANWA KAGAKU KENKYUSHO CO LTD   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DYNEMICIN A;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA P 388; MOUSE; NONHUMAN; SQUAMOUS CELL CARCINOMA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTHRAQUINONES; ANTIBIOTICS, ANTINEOPLASTIC; CELL DEATH; CELL LINE; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; ENEDIYNES; HUMANS; LEUKEMIA P388; MICE; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; WATER;

ANIMALIA;

EID: 0030987443     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00037-0     Document Type: Article

References (66)

1. For reviews of the cyclic enediynes, see: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387.
2. (b) Nicolaou, K. C.; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. USA 1993, 90, 5881.
3. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
4. (d) Lhermitte, H.; Grierson, D. S. Contemporary Organic Synthesis, 1996, 3, 93.
5. (a) Konishi, M.; Ohkuma, H.; Matsumoto, K.; Kamei, T.; Miyaki, T.; Oki, T. ; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449.
6. (b) Kamei, H.; Nishiyama, Y;. Takahashi, A.; Obi, Y.; Oki, T. J. Antibiot. 1991, 44, 1306.
7. (c) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
8. (a) Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464.
9. (b) Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
10. (a) Golik, J.; Clardy, J.; Dubay, G.; Groennewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; W. Doyle, T. J. Am. Chem. Soc. 1987, 109, 3461.
11. (b) Golik, J.; Dubay, G.; Groennewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 709, 3462.
12. Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331.
13. Leet, J. E.; Schroeder, D. R.; Hofstead, S.; Golik, J. J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946.
14. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637.
15. (a) Hanada, M.; Ohkuma, H.; Yonemoto, T.; Tomita, K.; Ohbayashi, M.; Kamei, H.; Miyaki, T.; Konishi, M.; Kawaguchi, H.; Forenza, S. J. Antibiot. 1991, 44, 403.
16. (b) Schroeder, D. R.; Colson, K. L.; Klohr, S. E.; Zein, N.; Langley, D. R.; Lee, M. S.; Matson, J. A.; Doyle, T. W. J. Am. Chem. Soc. 1994, 116, 9531.
17. For the synthesis of methylated dynemicin A, see: Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378.
18. For the total synthesis of (+)-dynemicin A, see: (a) Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33.
19. (b) Myers, A. G.; Fraley, M. E.; Tom, N. J. J. Am. Chem. Soc. 1994, 116, 11556.
20. For the total synthesis of (±)-dynemicin A, see: (a) Shair, M. D.; Yoon, T. Y.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1721.
21. (b) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16.
22. (c) Shair, M. D.; Yoon, T. Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509.
23. (a) Sugiura, Y.; Shiraki, T.; Konishi, M.; Oki, T. Proc. Natl. Acad. Sci. USA 1990, 87, 3831.
24. (b) Kusakabe, T.; Maekawa, K.; Ichikawa, A.; Uesugi, M.; Sugiura, Y. BioChem. 1993, 32, 11669.
25. Snyder, J. P.; Tipsword, G. E. J. Am. Chem. Soc. 1990, 112, 4040.
26. Semmelhack, M. F.; Gallagher, J.; Cohen, D. Tetrahedron Lett. 1990, 34, 1521.
27. Wender, P. A.; Kelly, R. C.; Beckham, S.; Miller, B. L. Proc. Natl. Acad. Sci. USA 1991, 88, 8835.
28. Langley, D. R.; Doyle, T. W.; Beveridge, D. L. J. Am. Chem. Soc. 1991, 113, 4395.
29. Myers, A. G.; Cohen, S. B.; Tom, N. J.; Madar, D. J.; Fraley, M. E. J. Am. Chem. Soc. 1995, 117, 7574.
30. For the correlation between the atomic distance and reactivity of Bergman cycloaromalization in the 1,5-diyne-3-ene system, see: (a) Nicolaou, K. C.; Zuccarello, G.; Ogawa, Y.; Schweiger, E. J.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 4866.
31. (b) Nicolaou, K. C.; Zuccarello, G.; Reimer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 7360.
32. (a) Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660.
33. (b) Lockhart, T. P.; Gomita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091.
34. (c) Darby, N.; Kim, C. U.; Salaun, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. J. Chem. Soc. Chem. Commun. 1971, 1516.
35. For review, see: Maier, M. E. Synlett 1995, 13 and references cited therein.
36. (a) Nicolaou, K. C.; Smith, A. L.; Wendeborn, S. V.; Hwang, C.-K. J. Am. Chem. Soc. 1991, 113, 3106.
37. (b) Nicolaou, K. C.; Hong, Y.-P.; Torisawa, Y.; Tasy, S.-C; Dai, W.-M. J. Am. Chem. Soc. 1991, 113, 9878.
38. (c) Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendborn, S. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890.
39. (d) Nicolaou, K. C.; Dai. W.-M. J. Am. Chem. Soc. 1992, 114, 8908.
40. (e) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172.
41. (f) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Wrasidlo, W. Bioorg. Med. Chem. Lett. 1992, 2 , 1155.
42. (g) Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39 , 2103.
43. (a) Wender, P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311.
44. (b) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867.
45. (c) Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278.
46. (a) Shair, M. D.; Yoon, T. Y.; Chou, D.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 2477.
47. (b) Chou, D.; Shair, M. D.; Yoon, T. Y.; Zheng, Y. H.; Danishefsky, S. J. Proc. Am. Assoc. Cancer Res. 1995, 36, 384.
48. Hay, M. P.; Wilson, W. R.; Denny, W. A. Bioorg. Med. Chem. Lett. 1995, 5, 2829.
49. Magnus, P.; Eisenbeis, S. A. J. Am. Chem. Soc. 1995, 115, 12627.
50. (a) Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 99.
51. (b) Nishikawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393.
52. (c) Nishikawa, T.; Ino, A.; Isobe, M.; Goto, T. Chem. Lett. 1991, 1271.
53. (d) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619.
54. (e) Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449-1468.
55. (f) Nishikawa, T.; Yoshikai, M.; Obi, K.; Isobe, M. Tetrahedron Lett. 1994, 35, 7997.
56. (g) Nishikawa, T.; Yoshikai, M.; Obi, K.; Kawai, T.; Unno, R.; Jomori, T.; Isobe, M. Tetrahedron 1995, 51, 9339.
57. (h) Nishikawa, T.; Moku, M.; Suzuki, Y.; Isobe, M. Chem. Lett. 1996, 113.
58. (i) Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Chem. Pharm. Bull. 1997, 45, 125.
59. (j) Unno, R.; Michishita, H.; Inagaki, H.; Suzuki, Y.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Bioorg. Med. Chem. in press,
60. (k) Unno, R.; Michishita, H.; Inagaki, H.; Suzuki, Y.; Baba, Y.; Jomori, T.; Moku, M.; Nishikawa, T.; Isobe, M. Bioorg. Med. Chem. in press.
61. For the synthesis of 1-azabicyclo[3.3.0]oct-5-ylmethylamine, see: (a) Miyano, S.; Somehara, T.; Nakao, M.; Sumoto, K. Synthesis 1978, 701.
62. (b) Unno, R.; Matsumoto, Y.; Kimura, H.; Oka, M.; Kondo, Y.; Kurono, M.; Sawai, K. U.S. Patent 4897495, 1990.
63. (c) Unno, R.; Matsumoto, Y.; Kimura, H.; Oka, M.; Kondo, Y.; Kurono, M.; Sawai, K. U.S. Patent 4985569, 1991.
64. For the DNA cleavage studies on dynemicin A analogues, see refs 17, 21, 22b, 22c, 23, 26e, 26g, 26i, 26j, and 26k.
65. For the studies on the in vitro cytotoxicity of dynemicin A analogues, see refs 11c, 21e, 21g, 23, 25, 26i, 26j, and 26k.
66. For the studies on the in vivo antitumor activity of dynemicin A analogues, see refs 11c, 23, 25, 26i, 26j, and 26k.