Synthesis and biological activity of artificial analogs of mycalamide A

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 16, 1997, Pages 2081-2086

  Fukui, Hideto ^a   Tsuchiya, Yoshinori ^a   Fujita, Keiko ^a   Nakagawa, Tadakiyo ^b   Koshino, Hiroyuki ^b   Nakata, Tadashi ^b  

^a KAKEN PHARMACEUTICAL CO LTD   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; FLUOROURACIL; MYCALAMIDE A; MYCALAMIDE A DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; NONHUMAN; REACTION ANALYSIS; SPONGE; VARICELLA ZOSTER VIRUS;

EID: 0030837966     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00365-X     Document Type: Article

References (32)

1. (a) Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Pannell, L. K. J. Am. Chem. Soc. 1988, 110, 4850.
2. (b) Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Thompson, A. M. J. Org. Chem. 1990, 55, 223.
3. (a) Sakemi, S.; Ichiba, T.; Kohmoto, S.; Saucy, G.; Higa, T. J. Am. Chem. Soc. 1988, 110, 4851.
4. (b) Matsunaga, S.; Fusetani, N.; Nakao, Y. Tetrahedron 1992, 48, 8369.
5. (c) Kobayashi, J.; Itagaki, F.; Shigemori, H., Sasaki, T. J. Nat. Prod. 1993, 56, 976.
6. Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828.
7. (a) Cardani, C.; Ghiringhelli, D.; Mondelli, R.; Quilico, A. Tetrahedron Lett. 1965, 2537.
8. (b) Matsumoto, T.; Yanagiya, M.; Maeno, S.; Yasuda, S. Tetrahedron Lett. 1968, 6297.
9. (c) Furusaki, A.; Watanabe, T.; Matsumoto, T.; Yanagiya, M. Tetrahedron Lett. 1968, 6301.
10. (a) Burres, N. S.; Clement, J. J. Cancer Res. 1989, 49, 2935.
11. (b) Ogawara, H.; Higashi, K.; Uchino, K.; Perry, N. B. Chem. Pharm. Bull. 1991, 39, 2152.
12. Galvin, F.; Freeman, G. J.; Razi-Wolf, Z.; Benacerraf, B.; Nadler, L.; Reiser, H. Eur. J. Immunol. 1993, 23, 283.
13. (a) Hong, C. Y.; Kishi, Y. J. Org. Chem. 1990, 55, 4242.
14. (b) Hong, C. Y.; Kishi, Y. J. Am. Chem. Soc. 1991, 113, 9693.
15. (c) Nakata, T.; Matsukura, H.; Jian, D. L.; Nagashima, H. Tetrahedron Lett. 1994, 35, 8229.
16. (d) Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159.
17. (e) Roush, W. R.; Marron, T. G. Tetrahedron Lett. 1993, 34, 5421.
18. (f) Marron, T. G.; Roush, W. R. Tetrahedron Lett. 1995, 36, 1581.
19. (g) Roush, W. R.; Marron, T. G.; Pfeifer, L. A. J. Org. Chem. 1997, 62, 474.
20. (h) Hoffmann, R. W.; Schlapbach, A. Tetrahedron Lett. 1993, 34, 7903.
21. (i) Hoffmann, R. W.; Breitfelder, S.; Schlapbach, A. Helv. Chim. Acta 1996, 79, 346.
22. (j) Davis, J.; Kocienski, P. J.; Boyle, T. Pol. J. Chem. 1994, 68, 2249.
23. (k) Kocienski, P.; Raubo, P.; Davis, J. K.; Boyle, F. T.; Davies, D. E.; Richter, A. J. Chem. Soc. Perkin Trans. 1 1996, 1797.
24. (a) Thompson, A. M.; Blunt, J. W.; Munro, M. H. G.; Perry, N. B.; Pannel, L. K. J. Chem. Soc. Perkin Trans. 1 1992, 1335.
25. (b) Thompson, A. M.; Blunt, J. W.; Munro, M. H. G; Clark, B. M. J. Chem. Soc. Perkin Trans. 1 1994, 1025.
26. (c) Thompson, A. M.; Blunt, J. W.; Munro, M. H. G; Perry N. B. J. Chem. Soc. Perkin Trans. 1 1995, 1233.
27. (a) Nakata, T.; Nagao, S.; Mori, N.; Oishi, T. Tetrahedron Lett. 1985, 26, 6461.
28. (b) Nakata, T.; Nagao, S.; Oishi, T. Tetrahedron Lett. 1985, 26, 6465.
29. 3P=CHCOOMe, benzene, reflux.
30. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
31. 50.
32. Tada, H.; Shiho, O.; Kuroshima, K.; Koyama, M.; Tsukamoto, K. J. Immunol. Method 1986, 93, 157.