Synthesis and biological activities of new conformationally restricted analogues of (-)-indolactam-V: Elucidation of the biologically active conformation of the tumor-promoting teleocidins

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10733-10743

  Irie, Kazuhiro ^a   Isaka, Tomomi ^a   Iwata, Yoriko ^a   Yanai, Yoshiaki ^a   Nakamura, Yoshimasa ^a   Koizumi, Fumito ^a   Ohigashi, Hajime ^a   Wender, Paul A ^b   Satomi, Yoshiko ^c   Nishino, Hoyoku ^c  

^a KYOTO UNIVERSITY   (Japan)

^b STANFORD UNIVERSITY   (United States)

^c KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLACTAM V; PROTEIN KINASE C; TELEOCIDIN;

ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; EPSTEIN BARR VIRUS; HELA CELL; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUMOR PROMOTION;

EID: 10544240767     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961727j     Document Type: Article

References (63)

1. Endo, Y.; Shudo, K.; Okamoto, T. Chem. Pharm. Bull. 1982, 30, 3457-3460.
2. Irie, K.; Hirota, M.; Hagiwara, N.; Koshimizu, K.; Hayashi, H.; Murao, S.; Tokuda, H.; Ito, Y. Agric. Biol. Chem. 1984, 48, 1269-1274.
3. For a review, see: Fujiki, H.; Sugimura, T. Adv. Cancer Res. 1987, 49, 223-264.
4. Nishizuka, Y. Nature 1984, 308, 693-698.
5. For reviews, see: Irie, K. Nippon Nogeikagaku Kaishi 1994, 68, 1289-1296. Endo, Y.; Ohno, M.; Shudo, K. Yakugaku Zasshi 1994, 114, 464-477. Irie, K.; Koshimizu, K. Comments Agric. Food Chem. 1993, 3, 1-25. Irie, K.; Koshimizu, K. The indole alkaloid tumor promoter teleocidins as Epstein-Barr virus inducers: structure, biosynthesis and structure-activity relationship. In Natural Products as Antiviral Agents; Chu, C. K., Cutler, H. G., Eds.; Plenum Press: New York, 1992; pp 257-273.
6. For reviews, see: Irie, K. Nippon Nogeikagaku Kaishi 1994, 68, 1289-1296. Endo, Y.; Ohno, M.; Shudo, K. Yakugaku Zasshi 1994, 114, 464-477. Irie, K.; Koshimizu, K. Comments Agric. Food Chem. 1993, 3, 1-25. Irie, K.; Koshimizu, K. The indole alkaloid tumor promoter teleocidins as Epstein-Barr virus inducers: structure, biosynthesis and structure-activity relationship. In Natural Products as Antiviral Agents; Chu, C. K., Cutler, H. G., Eds.; Plenum Press: New York, 1992; pp 257-273.
7. For reviews, see: Irie, K. Nippon Nogeikagaku Kaishi 1994, 68, 1289-1296. Endo, Y.; Ohno, M.; Shudo, K. Yakugaku Zasshi 1994, 114, 464-477. Irie, K.; Koshimizu, K. Comments Agric. Food Chem. 1993, 3, 1-25. Irie, K.; Koshimizu, K. The indole alkaloid tumor promoter teleocidins as Epstein-Barr virus inducers: structure, biosynthesis and structure-activity relationship. In Natural Products as Antiviral Agents; Chu, C. K., Cutler, H. G., Eds.; Plenum Press: New York, 1992; pp 257-273.
8. For reviews, see: Irie, K. Nippon Nogeikagaku Kaishi 1994, 68, 1289-1296. Endo, Y.; Ohno, M.; Shudo, K. Yakugaku Zasshi 1994, 114, 464-477. Irie, K.; Koshimizu, K. Comments Agric. Food Chem. 1993, 3, 1-25. Irie, K.; Koshimizu, K. The indole alkaloid tumor promoter teleocidins as Epstein-Barr virus inducers: structure, biosynthesis and structure-activity relationship. In Natural Products as Antiviral Agents; Chu, C. K., Cutler, H. G., Eds.; Plenum Press: New York, 1992; pp 257-273.
9. Endo, Y.; Shudo, K.; Itai, A.; Hasegawa, M.; Sakai, S. Tetrahedron 1986, 42, 5905-5924.
10. Wender, P. A.; Cribbs, C. M. Computer assisted molecular design related to the protein kinase C receptor. In Advances in Medicinal Chemistry; Maryanoff, C. A., Maryanoff, B. E., Eds.; JAI Press Inc.: London, 1992; Vol. 1, pp 1-53.
11. Jeffrey, A. M.; Liskamp, R. M. J. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 241-245.
12. Wender, P. A.; Koehler, K. F.; Sharkey, N. A.; Dell'Aquila, M. L.; Blumberg, P. M. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4214-4218.
13. Itai, A.; Kato, Y.; Tomioka, N.; Iitaka, Y.; Endo, Y.; Hasegawa, M., Shudo, K.; Fujiki, H.; Sakai, S. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3688-3692.
14. Wender, P. A.; Cribbs, C. M.; Koehler, K. F.; Sharkey, N. A.; Herald, C. L.; Kamano, Y.; Pettit, G. R.; Blumberg, P. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 7197-7201.
15. Thomson, C.; Wilkie, J. Carcinogenesis 1989, 10, 531-540.
16. Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672-9676.
17. Rando, R. R.; Kishi, Y. Biochemistry 1992, 31, 2211-2218.
18. Huisgen, R.; Brade, H.; Walz, H.; Glogger, I. Chem. Ber. 1957, 90, 1437-1447.
19. Williamson, K. L.; Roberts, J. D. J. Am. Chem. Soc. 1976, 98, 5082-5086.
20. Ohno, M.; Endo, Y.; Hirano, M.; Itai, A.; Shudo, K. Tetrahedron Lett. 1993, 34, 8119-8122.
21. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841-1855.
22. Kozikowski, A. P.; Ma, D.; Pang, Y.-P.; Shum, P.; Likic, V.; Mishra, P. K.; Macura, S.; Basu, A.; Lazo, J. S.; Ball, R. G. J. Am. Chem. Soc. 1993, 115, 3957-3965.
23. Irie, K.; Koizumi, F.; Iwata, Y.; Ishii, T.; Yanai, Y.; Nakamura, Y.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 453-458.
24. Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100.
25. For a review, see: Lutz, R. P. Chem. Rev. 1984, 84, 205-247.
26. Caution: Indolactams are tumor promoters and should be handled with care.
27. Nakatsuka, S.; Masuda, T.; Sakai, K.; Goto, T. Tetrahedron Lett. 1986, 27, 5735-5738.
28. Kogan, T. P.; Somers, T. C.; Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
29. 13C NMR where relevant, EI-MS, and high-resolution (HR) EI-MS.
30. Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800-5807.
31. Irie, K.; Hagiwara, N.; Koshimizu, K. Tetrahedron 1987, 43, 5251-5260.
32. Okuno, S.; Irie, K.; Suzuki, Y.; Koshimizu, K.; Nishino, H.; Iwashima, A. Bioorg. Med. Chem. Lett. 1994, 4, 431-434.
33. Irie, K.; Okuno, S.; Koizumi, F.; Koshimizu, K.; Nishino, H.; Iwashima, A. Tetrahedron 1993, 49, 10817-10830.
34. Irie, K.; Kajiyama, S.; Funaki, A.; Koshimizu, K.; Hayashi, H.; Arai, M. Tetrahedron 1990, 46, 2773-2788.
35. Endo, Y.; Ohno, M.; Hirano, M.; Kawai, T.; Takeda, M.; Itai, A.; Shudo, K. Conformations of indolactam derivatives: prediction, observation and relation to biological activity. In Symposium Papers of 34th Meeting of the Chemistry of Natural Products; Tokyo, 1992; pp 739-746.
36. Irie, K.; Hagiwara, N.; Tokuda, H.; Koshimizu, K. Carcinogenesis 1987, 8, 547-552.
37. Fujiki, H.; Suganuma, M.; Ninomiya, M.; Yoshizawa, S.; Yamashita, K.; Takayama, S.; Hitotsuyanagi, Y.; Sakai, S.; Shudo, K.; Sugimura, T. Cancer Res. 1988, 48, 4211-4214.
38. Casnati, G.; Francioni, M.; Guareschi, A.; Pochini, A. Tetrahedron Lett. 1969, 2485-2487.
39. Yamashita, T.; Imoto, M.; Isshiki, K.; Sawa, T.; Naganawa, H.; Kurasawa, S.; Zhu, B.-Q.; Umezawa, K. J. Nat. Prod. 1988, 51, 1184-1187.
40. For a review, see: Grundon, M. F. Tetrahedron 1978, 34, 143-161.
41. For a review, see: Protein Kinase C Current Concepts and Future Perspectives; Lester, D. S., Epand, R. M., Eds.; Ellis Horwood: West Sussex, England, 1992.
42. Wender, P. A.; Irie, K.; Miller, B. L. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 239-243.
43. Irie, K.; Yanai, Y.; Ohigashi, H.; Wender, P. A.; Miller, B. L. Bioorg. Med. Chem. Lett. 1996, 6, 353-356.
44. James, H. G. Probit procedure. In SAS User's Guide; Jane, T. H., Kathryn, A. C., Eds.; SAS Institute: Cary, NC, 1979; pp 357-360.
45. Sharkey, N. A.; Blumberg, P. M. Cancer Res. 1985, 45, 19-24.
46. Kazanietz, M. G.; Areces, L. B.; Bahador, A.; Mischak, H.; Goodnight, J.; Mushinski, J. F.; Blumberg, P. M. Mol. Pharmacol. 1993, 44, 298-307.
47. Dimitrijevic, S. M.; Ryves, W. J.; Parker, P. J.; Evans, F. J. Mol. Pharmacol. 1995, 48, 259-267.
48. Quest, A. F. G.; Bardes, E. S. G.; Bell, R. M. J. Biol. Chem. 1994, 269, 2953-2960.
49. zur Hausen, H.; Bornkamm, G. W.; Schmidt, R.; Hecker, E. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 782-785.
50. Ito, Y.; Yanase, S.; Fujita, J.; Harayama, T.; Takashima, M.; Imanaka, H. Cancer Lett. 1981, 13, 29-37.
51. Murakami, A.; Tanaka, S.; Ohigashi, H.; Hirota, M.; Irie, R.; Takeda, N.; Tatematsu, A.; Koshimizu, K. Biosci. Biotechnol. Biochem. 1992, 56, 769-772.
52. Nishino, H.; Fujiki, H.; Terada, M.; Sato, S. Carcinogenesis 1983, 4, 107-110.
53. Rohrschneider, L. R.; Boutwell, R. K. Cancer Res. 1973, 33, 1945-1953.
54. Irie, K.; Okuno, S.; Kajiyama, S.; Koshimizu, K.; Nishino, H.; Iwashima, A. Carcinogenesis 1991, 12, 1883-1886.
55. Irie, K.; Iguchi, M.; Oda, T.; Suzuki, Y.; Okuno, S.; Ohigashi, H.; Koshimizu, K.; Hayashi, H.; Arai, M.; Nishino, H.; Iwashima, A. Tetrahedron 1995, 51, 6255-6266.
56. Hommel, U.; Zurini, M.; Luyten, M. Nat. Struct. Biol. 1994, 1, 383-387.
57. Ichikawa, S.; Hatanaka, H.; Takeuchi, Y.; Ohno, S.; Inagaki, F. J. Biochem. 1995, 117, 566-574.
58. Zhang, G.; Kazanietz. M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924.
59. We, K.; Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164-2173.
60. Fujiki, H.; Suganuma, M.; Nakayasu, M.; Tahira, T.; Endo, Y.; Shudo, K.; Sugimura, T. Jpn. J. Cancer Res. (Gann) 1984, 75, 866-870.
61. Kawai, T.; Ichinose, T.; Takeda, M.; Tomioka, N.; Endo, Y.; Yamaguchi, K.; Shudo, K.; Itai, A. J. Org. Chem. 1992, 57, 6150-6155.
62. Kawai, T.; Ichinose, T.; Endo, Y.; Shudo, K.; Itai, A. J. Med. Chem. 1992, 35, 2248-2253.
63. Irie, K.; Koshimizu, K. Mem. Coll. Agric., Kyoto Univ. 1988, 132, 1-59.