Conformational studies and structure-activity analysis of lissoclinamide 7 and related cyclopeptide alkaloids

Journal of the American Chemical Society

Volumn 120, Issue 17, 1998, Pages 4105-4112

  Wipf, Peter ^a   Fritch, Paul C ^a   Geib, Steven J ^a   Sefler, Andrea M ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; CYCLOPEPTIDE; LISSOCLINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

LISSOCLINUM;

EID: 0032490079     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973580h     Document Type: Article

References (61)

1. (a) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 233.
3. (c) Flam, F. Science 1994, 266, 1324.
4. (d) Faulkner, D. J. Nat. Prod. Rep. 1994, 11, 355.
5. (e) Marine Biotechnology, Volume 1: Pharmaceutical and Bioactive Marine Natural Products; Attaway, D. H., Zaborsky, O. R., Eds.; Plenum Publishers: New York, 1993.
6. (f) Faulkner, D. J. Chem. Rev. 1993, 93, 1671.
7. See, for example: (a) Wipf, P.; Lim, S. Chimia 1996, 50, 157. (b) Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. Chem. Biol. 1994, 1, 67. (c) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449.
8. See, for example: (a) Wipf, P.; Lim, S. Chimia 1996, 50, 157. (b) Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. Chem. Biol. 1994, 1, 67. (c) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449.
9. See, for example: (a) Wipf, P.; Lim, S. Chimia 1996, 50, 157. (b) Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. Chem. Biol. 1994, 1, 67. (c) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449.
10. Wipf, P.; Fritch, P. C. J. Am. Chem. Soc. 1996, 118, 12358.
11. Hawkins, C. J.; Lavin, M. F.; Marshall, K. A.; Brenk, A. L. v. d.; Watters, D. J. J. Med. Chem. 1990, 33, 1634.
12. For recent reviews of Lissoclinum peptides, see: (a) Wipf, P. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: In press, (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Davidson, B. S. Chem. Rev. 1993, 93, 1771.
13. For recent reviews of Lissoclinum peptides, see: (a) Wipf, P. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: In press, (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Davidson, B. S. Chem. Rev. 1993, 93, 1771.
14. For recent reviews of Lissoclinum peptides, see: (a) Wipf, P. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: In press, (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Davidson, B. S. Chem. Rev. 1993, 93, 1771.
15. Abbenante, G.; Fairlie, D. P.; Gahan, L. R.; Hanson, G. R.; Pierens, G. K.; van den Brenk, A. L. J. Am. Chem. Soc. 1996, 118, 10384.
16. (a) Wipf, P.; Venkatraman, S.; Miller, C. P.; Geib. S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1516.
17. (b) van den Brenk, A. L.; Byriel, K. A.; Fairlie, D. P.; Gahan. L. R.; Hanson, G. R.; Hawkins, C. J.; Jones, A.; Kennard, C. H. L.; Moubaraki, B.; Murray, K. S. Inorg. Chem. 1994, 33, 3549.
18. (c) van den Brenk, A. L.; Fairlie, D. P.; Hanson, G. R.; Gahan, L. R.; Hawkins, C. J.; Jones, A. Inorg. Chem. 1994, 33, 2280.
19. (d) van den Brenk. A.; Fairlie, D. P.; Gahan, L. R.; Hanson, G. R.; Hambley, T. W. Inorg. Chem. 1996, 35, 1095.
20. see also: (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1.
21. For a review, see: Fairlie, D. P.; Abbenante. G.; March, D. R. Curr. Med. Chem. 1995, 2, 654 and references therein.
22. Hambley. T. W.; Hawkins, C. J.; Lavin, M. F.; Brenk, A. v. d.; Watters, D. J. Tetrahedron 1992, 48, 341.
23. ( 10) Prinsep, M. R.; Moore, R. E.; Levine, I. A.; Patterson, G. M. L. J. Nat. Prod. 1992, 55, 140.
24. Ireland, C.; Scheuer, P. J. J. Am. Chem. Soc. 1980, 102, 5688.
25. Biskupiak, J. E.; Ireland, C. M. J. Org. Chem. 1983, 48, 2302.
26. Hamamoto, Y.; Endo, M.; Nakagawa, M.; Nakanishi, T.; Mizukawa, K. J. Chem. Soc., Chem. Commun. 1983, 323.
27. Hamada, Y.; Kato, S.; Shioiri, T. Tetrahedron Lett. 1985. 26, 3223.
28. (a) Shioiri, T.; Hamada, Y.; Kato. S.; Shibata, M.; Kondo, Y.; Nakagawa, H.; Kohda, K. Biochem. Pharm. 1987, 36. 4181.
29. (b) Kohda, K.: Ohta, Y.; Kawazoe, Y.; Kato, T.; Suzumura, Y.; Hamada, Y.; Shioiri, T. Biochem. Pharm. 1989, 38, 4500.
30. (c) Kohda, K.; Ohta, Y.; Yokoyama, Y.; Kawazoe, Y.; Kato, T.; Suzumura, Y.; Hamada, Y.; Shioiri, T. Biochem. Pharm. 1989, 38, 4497.
31. McDonald, L. A.; Foster, M. P.; Phillips, D. R.; Ireland, C. M.; Lee, A. Y.; Clardy, J. J. Org. Chem. 1992, 57, 4616.
32. Wasylyk, J. M.; Biskupiak, J. E.; Costello, C. E.; Ireland, C. M. J. Org. Chem. 1983, 48, 4445.
33. Degnan. B. M.; Hawkins, C. J.; Lavin, M. F.; McCaffrey, E. J.; Parry, D. L.; Brenk, A. L. v. d.; Watters, D. J. J. Med. Chem. 1989, 32, 1349.
34. Schmitz, F. J.; Ksebati, M. B.; Chang. J. S.; Wang. J. L.; Hossain, M. B.; Helm, D. v. d.; Engel, M. H.; Serban, A.; Silfer, J. A. J. Org. Chem. 1989. 54, 3463.
35. Ireland, C. M.; Durso, A. R.; Newman, R. A.; Hacker, M. P. J. Org. Chem. 1982, 47, 1807.
36. Toske, S. G.; Fenical, W. Tetrahedron Lett. 1995, 36, 8355.
37. (a) In, Y.; Doi, M.; Inoue, M.; Ishida, T.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1993, 41. 1686.
38. (b) In, Y.; Doi, M.; Inoue, M.; Ishida, T.; Hamada, Y.; Shioiri, T. Acta Crystallogr. 1994, C50. 432.
39. (c) Ishida, T.; Ohishi, H.; Inoue. M.; Kamigauchi, M.; Sugiura, M.; Takao, N.; Kato, S.; Hamada, Y.; Shioiri, T. J. Org. Chem. 1989, 54, 5337.
40. Ishida, T.; In, Y.; Shinozaki, F.; Doi, M.; Yamamoto, D.; Hamada, Y.; Shioiri, T.; Kamigauchi, M.; Sugiura, M. J. Org. Chem. 1995, 60, 3944.
41. McDonald, L. A.; Foster, M. P.; Phillips, D. R.; Ireland, C. M.; Lee, A. Y.; Clardy, J. J. Org. Chem. 1992, 57, 4616.
42. Wipf, P.; Venkatraman, S.; Miller, C. P.; Grant, C. M. Unpublished results.
43. Boden, C. D. J.; Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1996, 37, 9111.
44. Ishida, T.; Inoue, M.; Hamada, Y.; Kato, S.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 370.
45. The atomic coordinates for this work are available on request from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K. Any request should be accompanied by the full literature citation for this article.
46. 3) and 0° (ψ): Chou, P. Y.; Fasman, G. D. J. Mol. Biol. 1977, 115, 135-75.
47. Boyd, M. R.; Paull, K. D. Drug Dev. Res. 1995, 34, 91 and references therein.
48. Due the scarcity of natural material, no direct comparison with synthetic compound could be made in our bioassays.
49. See, for example: Pettit, G. R.; Taylor, S. R. J. Org. Chem. 1996, 61, 2322.
50. 2O-organic solvent mixtures were not used due to (a) the very low solubility of lissoclinamide 7 in aqueous environments and (b) the known problems with viscosity effects in NOE studies in DMSO-or acetonitrile-water mixtures: Amodeo, P.; Motta, A.; Picone, D.; Saviano, G.; Tancredi, T.; Temussi, P. A. J. Magn. Reson. 1991, 95, 201.
51. States, D. J.; Haberkorn, R. A.; Ruben, D. J. J. Magn. Reson. 1982, 48, 286.
52. von Kienlin, M.; Moonen, C. T. W.; van der Toorn, A.; van Zijl, P. C. M. J. Magn. Reson. 1991, 93, 423.
53. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355.
54. Levitt, M.; Freeman, R.; Frenkiel, T. J. Magn. Reson. 1982, 47, 328.
55. Bodenhausen, G.; Kogler, K.; Ernst, R. R. J. Magn. Reson. 1984, 58, 370.
56. Kessler, H.; Griesinger, G.; Kerssebaum, R.; Wagner, K.; Ernst, R. R. J. Am. Chem. Soc. 1987, 109, 607.
57. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J Comput. Chem. 1990, 11, 440.
58. McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743.
59. Hasel, W.; Hendrickson, T. F.; Still, W. C. Tetrahedron Comput. Methodol. 1988, 1,103.
60. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
61. The corresponding Φ angles were determined according to the following: Pardi, A.; Billeter, M.; Wüthrich, K. J. Mol. Biol. 1984, 80, 741.