Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins

Journal of the American Chemical Society

Volumn 118, Issue 8, 1996, Pages 1841-1855

  Endo, Yasuyuki ^a   Ohno, Michihiro ^a   Hirano, Masaaki ^a   Itai, Akiko ^b   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Inst of Medicinal Molecular Design   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOLACTAM DERIVATIVE; INDOLOLACTAM V; TELEOCIDIN; UNCLASSIFIED DRUG;

ARTICLE; CELL DIFFERENTIATION; CELL STRAIN HL 60; DRUG STRUCTURE; DRUG SYNTHESIS; MODEL; NUCLEAR MAGNETIC RESONANCE;

EID: 0030011941     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953578v     Document Type: Article

References (45)

1. Fujiki, H.; Mon, M.; Nakayasu, M.; Terada, M.; Sugimura, T. Biochem. Biophys. Res. Commun. 1979, 90, 976-983. Fujiki, H.; Mori, M.; Nakayasu, M.; Terada, M.; Sugimura, T.; Moore, R. E. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3872-3876,. Fujiki, H.; Suganuma, M. Adv. Cancer Res. 1987, 49, 223-264.
2. Fujiki, H.; Mon, M.; Nakayasu, M.; Terada, M.; Sugimura, T. Biochem. Biophys. Res. Commun. 1979, 90, 976-983. Fujiki, H.; Mori, M.; Nakayasu, M.; Terada, M.; Sugimura, T.; Moore, R. E. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3872-3876,. Fujiki, H.; Suganuma, M. Adv. Cancer Res. 1987, 49, 223-264.
3. Fujiki, H.; Mon, M.; Nakayasu, M.; Terada, M.; Sugimura, T. Biochem. Biophys. Res. Commun. 1979, 90, 976-983. Fujiki, H.; Mori, M.; Nakayasu, M.; Terada, M.; Sugimura, T.; Moore, R. E. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3872-3876,. Fujiki, H.; Suganuma, M. Adv. Cancer Res. 1987, 49, 223-264.
4. Endo, Y.; Shudo, K.; Okamoto, T. Chem. Pharm. Bull. 1982, 30, 3457-3460. Endo, Y.; Shudo, K.; Furuhata, K.; Ogura, H.; Sakai, S.; Aimi, N.; Hitotsuyanagi, Y.; Koyama, Y. Chem. Pharm. Bull. 1984, 32, 358-361.
5. Endo, Y.; Shudo, K.; Okamoto, T. Chem. Pharm. Bull. 1982, 30, 3457-3460. Endo, Y.; Shudo, K.; Furuhata, K.; Ogura, H.; Sakai, S.; Aimi, N.; Hitotsuyanagi, Y.; Koyama, Y. Chem. Pharm. Bull. 1984, 32, 358-361.
6. Hayashi, H.; Murao, S.; Tokuda, H.; Ito, Y. Agric. Biol. Chem. 1984, 48, 1269-1274.
7. Fujiki, H.; Suganuma, M.; Nakayasu, M.; Tahira, T.; Endo, Y.; Shudo, K.; Sugimura, T. Jpn. J. Cancer Res. (Gann) 1984, 75, 866-870.
8. deLaszlo, S E.; Ley, S. V.; Porter, R. A. J. J. Chem. Soc., Chem. Commun. 1986, 344-346. Matsuda, T.; Nakatsuka, S.; Goto, T. Agric. Biol. Chem. 1989, 53, 2257-2260. Kozikowski, A. P.; Sato, K.; Basu, A.; Lazo, J. S. J. Am. Chem. Soc. 1989, 111, 6228-6234, Kogan, T. P.; Somers, T. C.: Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
9. deLaszlo, S E.; Ley, S. V.; Porter, R. A. J. J. Chem. Soc., Chem. Commun. 1986, 344-346. Matsuda, T.; Nakatsuka, S.; Goto, T. Agric. Biol. Chem. 1989, 53, 2257-2260. Kozikowski, A. P.; Sato, K.; Basu, A.; Lazo, J. S. J. Am. Chem. Soc. 1989, 111, 6228-6234, Kogan, T. P.; Somers, T. C.: Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
10. deLaszlo, S E.; Ley, S. V.; Porter, R. A. J. J. Chem. Soc., Chem. Commun. 1986, 344-346. Matsuda, T.; Nakatsuka, S.; Goto, T. Agric. Biol. Chem. 1989, 53, 2257-2260. Kozikowski, A. P.; Sato, K.; Basu, A.; Lazo, J. S. J. Am. Chem. Soc. 1989, 111, 6228-6234, Kogan, T. P.; Somers, T. C.: Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
11. deLaszlo, S E.; Ley, S. V.; Porter, R. A. J. J. Chem. Soc., Chem. Commun. 1986, 344-346. Matsuda, T.; Nakatsuka, S.; Goto, T. Agric. Biol. Chem. 1989, 53, 2257-2260. Kozikowski, A. P.; Sato, K.; Basu, A.; Lazo, J. S. J. Am. Chem. Soc. 1989, 111, 6228-6234, Kogan, T. P.; Somers, T. C.: Venuti, M. C. Tetrahedron 1990, 46, 6623-6632.
12. Endo, Y.; Shudo, K.; Itai, A.; Hasegawa, M , Sakai, S. Tetrahedron 1986, 42, 5905-5924.
13. Harada, H.; Sakabe, N.; Hirata, Y.; Nina, I. Tetrahedron Lett. 1966, 2523-2526.
14. Hitotsuyanagi, Y.; Yamaguchi, K.; Ogata, K ; Aimi, N., Sakai, S.; Koyama, Y.; Endo, Y.; Shudo, K.; Itai, A.; Iitaka, Y. Chem. Pharm. Bull 1984, 32, 3774-3778
15. Endo, Y.; Hasegawa, M ; Itai, A.; Shudo, K.; Ton, M.; Asakawa, Y., Sakai, S Tetrahedrom Lett. 1985, 26, 1069-1072.
16. Jeffrey, A. M.; Liskamp, R. M. J. Proc Natl. Acad. Sci. U.S.A. 1986, 83, 241-245. 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.
17. Jeffrey, A. M.; Liskamp, R. M. J. Proc Natl. Acad. Sci. U.S.A. 1986, 83, 241-245. 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.
18. The importance of the twist form of teleocidins has been referred to in: Irie, K.; Hayashi, H.; Arai, M.; Koshimizu, K. Agric. Biol. Chem. 1986, 50, 2679-2680. Although 5-chloroindolactam-V exists in the sofa form predominantly, the activity of the compound is 0.1 of that of indolactam-V in our differentiation assay of HL-60 cells.
19. Endo, Y.; Hasegawa, M.; Itai, A.; Shudo, K Tetrahedron 1987, 43, 3695-3704, Kajiyama, S.; Irie, K.; Kido, T.; Koshimizu, K.; Hayashi, H.; Arai, M. Tetrahedron 1991, 47, 5453-5462.
20. Endo, Y.; Hasegawa, M.; Itai, A.; Shudo, K Tetrahedron 1987, 43, 3695-3704, Kajiyama, S.; Irie, K.; Kido, T.; Koshimizu, K.; Hayashi, H.; Arai, M. Tetrahedron 1991, 47, 5453-5462.
21. Hirota, M.; Suganuma, M.; Yoshizawa, S., Horiuchi, T.; Nakayasu, M.; Hasegawa, M., Endo, Y.; Shudo, K.; Fujiki, H. Jpn. J. Cancer Res. (Gann) 1987, 78, 577-582.
22. Kawai, T.; Ichinose, T.; Endo, Y.; Shudo, K.; Itai, A. J. Med. Chem. 1992, 25, 2248-2253.
23. Kawai, T.; Ichinose, T.; Takeda, M.; Tomioka, N.; Endo, Y.; Yamaguchi, K.; Shudo, K.; Itai, A J. Org. Chem. 1992, 57, 6150-6155.
24. A part of this work has been reported in a preliminary form. Ohno, M ; Endo, Y.; Hirano, M., Itai, A., Shudo, K. Tetrahedron Lett. 1993, 34, 8119-8122.
25. Stewart, W E., Siddall, T. H., III. Chem. Rev. 1970, 70, 515-551. Huisgen, R.; Brade, H.; Walz, H.; Glogger, I. Chem. Ber 1957, 90, 1437-1447. Swenson, C A.; Chen, C. Y. S. J. Phys Chem. 1973, 77, 645-648.
26. Stewart, W E., Siddall, T. H., III. Chem. Rev. 1970, 70, 515-551. Huisgen, R.; Brade, H.; Walz, H.; Glogger, I. Chem. Ber 1957, 90, 1437-1447. Swenson, C A.; Chen, C. Y. S. J. Phys Chem. 1973, 77, 645-648.
27. Stewart, W E., Siddall, T. H., III. Chem. Rev. 1970, 70, 515-551. Huisgen, R.; Brade, H.; Walz, H.; Glogger, I. Chem. Ber 1957, 90, 1437-1447. Swenson, C A.; Chen, C. Y. S. J. Phys Chem. 1973, 77, 645-648.
28. Williamson, K. L., Roberts, J. D. J. Am. Chem. Soc. 1976, 98, 5082-5086.
29. Fujiki, H.; Suganuma, M.; Hakii, H.; Nakayasu, M.; Endo, Y ; Shudo, K.; Irie, K.; Koshimizu, K.; Sugimura, T. Proc. Jpn. Acad 1985, 61, 45-47.
30. Endo, Y.; Ohno, M., Hirano, M., Takeda, M.; Itai, A.; Shudo, K Biomed. Chem. Lett. 1994, 4, 491-494.
31. Endo, Y.; Sato, Y.; Shudo, K. Tetrahedron 1987, 43, 2241-2247. Irie, K.; Hayashi, H.; Arai, M., Koshimizu, K. Agric. Biol. Chem. 1986. 50, 2679-2680. Irie, K.; Hagiwara, N.; Tokuda, H.; Koshimizu, K. Carcinogenesis 1987, 8, 547-552.
32. Endo, Y.; Sato, Y.; Shudo, K. Tetrahedron 1987, 43, 2241-2247. Irie, K.; Hayashi, H.; Arai, M., Koshimizu, K. Agric. Biol. Chem. 1986. 50, 2679-2680. Irie, K.; Hagiwara, N.; Tokuda, H.; Koshimizu, K. Carcinogenesis 1987, 8, 547-552.
33. Endo, Y.; Sato, Y.; Shudo, K. Tetrahedron 1987, 43, 2241-2247. Irie, K.; Hayashi, H.; Arai, M., Koshimizu, K. Agric. Biol. Chem. 1986. 50, 2679-2680. Irie, K.; Hagiwara, N.; Tokuda, H.; Koshimizu, K. Carcinogenesis 1987, 8, 547-552.
34. Webb, R. R., Venuti, M. C.; Eigenbrot, C. J. Org. Chem. 1991, 56, 4706-4713.
35. Kogan, T. P.; Somers, T. C., Venun. M C Tetrahedron 1990, 46, 6623-6632.
36. Huberman, E ; Callaham, M. F. Proc. Natl. Acad. Sci. U S.A 1979, 76, 1293-1297.
37. Kozikowski, A. P., Ma, D.; Pang, Y.-P.; Shum, P., Likic, V.; Mishra, P. K.; Basu, A.; Lazo, J. S.; Ball, R. G. J. Am. Chem. Soc 1993, 115, 3957-3965.
38. 15 Similarly, in the case of (+)-43. the energy differences between the most stable r-cis-sofa form and the next most stable conformations (the twist, fold, and r-twist forms) are greater than 4.5 kcal/mol by MD calculation. The relative atomic positions of the amide bond and hydroxymethyl group of the stable r-cis-sofa form of (+)-43 are close to those of the twist form of (-)-6. The remarkable stability of the r-cis-sofa form of (+)-43 and the difference of activity between (-)-6 and (+)-43 suggested that the two compounds interact with the macromolecular receptor as the twist form and r-cis-sofa form, respectively.
39. Hashimoto, Y.: Shudo, K. Jpn. J. Cancer Res. (Gann) 1991, 82, 665-668.
40. Irie, K.; Koizumi, F.; Iwata, Y.; Ishii, T.; Yanai, Y.; Nakamura, Y.; Ohigashi, H.; Wender, P. A. BioMed. Chem. Lett. 1995, 5, 453-458.
41. 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.
42. Zhane, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917-924.
43. Brooks, G., Momce, N. A.; Ellis, C.; Aitken, A.; Evans, A. T.; Evans. F J. Toxicon 1987, 25, 1229-1233.
44. Portoghese, P. S.; Hanson, R. N.; Telang, V G., Winger, J. L. J. Med. Chem 1977, 20, 1020-1024.
45. Massy-Westropp, R A.; O. Warren, R. F. Aust. J. Chem. 1984, 37, 1969-1977.