Synthesis and initial structure-activity relationships of modified salicylihalamides

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4241-4243

  Wu, Yusheng ^a   Seguil, Olga R ^a   De Brabander, Jef K ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; SALICYLIC ACID;

ARTICLE; CELL CULTURE; CELL DIVISION; CHEMISTRY; DRUG EFFECT; HUMAN; MELANOMA; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; CELL DIVISION; HUMANS; MELANOMA; SALICYLIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0034727948     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0068086     Document Type: Article

References (29)

1. Erickson, K. L.; Beutler, J. A.; Cardellina II, J. H.; Boyd, M. R. J. Org. Chem. 1997, 62, 8188-8192.
2. Lobatamides: (a) McKee, T. C.; Galinis, D. L.; Pannell, L. K.; Cardellina, J. H., II; Laakso, J.; Ireland, C. M.; Murray, L.; Capon, R. J.; Boyd, M. R. J. Org. Chem. 1998, 63, 7805-7810.
3. (b) Lobatamide A is identical to the structure of YM-75518, see: Suzumura, K.-I.; Takahashi, I.; Matsumoto, H.; Nagai, K.; Setiawan, B.; Rantiatmodjo, R. M.; Suzuki, K.-I.; Nagano, N. Tetrahedron Lett. 1997, 38, 7573-7576.
4. CJ-12,950 and CJ-13,357: (d) Dekker: K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T.; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14-20.
5. Apicularens: (e) Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075-1080.
6. (f) Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2000, 913-919.
7. Oximidines: (g) Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153-155.
8. Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem., Int. Ed. 2000, in press.
9. For our synthetic efforts toward apicularen A, see: Bhattacharjee, A.; De Brabander, J. K. Tetrahedron Lett. 2000, 41, 8069-8073.
10. For other synthetic efforts, see: (a) Georg, G. I.; Blackman, B.; Mossman, C. J.; Yang, K.; Flaherty, P. T. Abstracts of Papers, 219th National Meeting of the American Chemical Society, San Francisco, March 2000; American Chemical Society: Washington, DC, 2000; ORGN 807.
11. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731-3734.
12. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569-8572.
13. For studies related to the enamide side chain, see: (d) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408.
14. (e) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399.
15. (f) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336.
16. (g) Stefanuti, I.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 3735-3738.
17. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
18. In our previously reported synthesis of (+)-salicylihalamide A, all three stereocenters in ent-4 were introduced by reagent-controlled reactions.1 The same chemistry was exploited for the preparation of 4, except for the use of antipodal chiral reagents.
19. Kunz, H.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 71-72.
20. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
21. 3 The spectroscopic data of the mixture (1 and 11) were in full accord with those previously obtained.
22. The corresponding enantiomers were completely devoid of activity in the same screen, indicating that biological function is at least partly dependent on a correctly configured macrolactone. We thank Dr. Michael R. Boyd (National Cancer Institute) for testing our compounds in the 60-cell line panel.
23. These dimers are presumably formed through reaction of the intermediate lithiated amide with a second molecule of isocyanate 10. For a similar observation, see ref 5e.
24. 50 0.07 μM).
25. Mitsunobu, O. Synthesis 1981, 1-28.
26. However, an intact side chain is not sufficient for biological activity; see footnote 11.
27. For an example of an enamide-containing natural product, and proposed modification of an N-acyliminium ion by an enzyme active site nucleophile, see: Gentle, C. A.; Bugg, T. D. H. J. Chem. Soc., Perkin Trans. 1 1999, 1274-1285.
28. Bieg, T.; Szeja, W. Synthesis 1985, 76-77.
29. 3