Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum: Structure elucidation and synthesis

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9850-9856

  Berlmck, Roberto G S ^a,c   Britton, Robert ^a   Piers, Edward ^a   Lim, Lynette ^a,b   Roberge, Michel ^a   Rosana Moreira Da Rocha, ^a,b   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXYSTAUROSPORINE; ANTINEOPLASTIC AGENT; DIDEMNIMIDE A; DIDEMNIMIDE D; DIDEMNIMIDE E; GRANULATIMIDE; ISOGRANULATIMIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; ASCIDIACEA; BIOASSAY; CANCER INHIBITION; CELL CYCLE G2 PHASE; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ISOLATION; DRUG SYNTHESIS; FRACTIONATION; HUMAN; HUMAN CELL; PHOTOLYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0032567379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981607p     Document Type: Article

References (36)

1. (a) Holloway, S. L.; Glotzer, M.; ICing, R. W.; Murray, A. W. Cell 1993, 73,1393.
2. (b) Weinert, T.; Lydall, D. Seminars Cancer Biol. 1993, 4, 129.
3. Nurse, P. Cell 1997, 91, 865.
4. Kao, G. D.; McKenna, W. G.; Maity, A.; Blank, K.; Muschel, R. J. Cancer Res. 1997, 57, 753.
5. (a) Hartwell, L.; Weinert, T.; Kadyk, L.; Garvick, B. Cold Spring Harbor Symp. Quantum Biol. 1994, 59, 259.
6. (b) Kaufmann, W. K.; Faules, R. S. FASEB J. 1996, 10, 238.
7. (a) Busse, P. M.; Böse, S. K.; Jones, R. W.; Tomlaeh, L. J. Radiât, Res. 1978, 76, 292.
8. (b) Schlegel, R.; Pardee, A. B. Science 1986, 232, 1264.
9. (c) Downes, C. S.; Musk, S. R. R.; Watson, J. V.; Johnston, R. T. J. Cell Biol. 1990, 110, 1855.
10. (d) Steinmann, K. E.; Belinski, G. S.; Lee, D.; Schlegel, R. Proc. Natl. Acad. Sci. USA 1991, 88, 6843.
11. (e) Andreassen, P. R.; Margolis, R. L. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2272.
12. (f) Tarn, S. W.; Schlegel, R. Cell Growth Differ. 1992,3, 811.
13. (g) Wang, Q.; Fan, S.; Eastman, A.; Worland, P. J.; Sausville, E. A.; O'Connor, P. M. J. Natl. Cancer Inst. 1996, 88, 956.
14. (a) Russell, K. J.; Wiens, L. W.; Demers, G. W.; Galloway, D. A.; Plon, S. E.; Groudine, M. Cancer Res. 1995, 55, 1639.
15. (b) Powell, S. N.; DeFrank, J. S.; Connell, P.; Eogan, M.; Prefier, F.; Dombkowski, D.; Tang, W.; Friend, S. Cancer Res. 1995, 55, 1643.
16. Russell, K. J.; Wiens, L. W.; Demers, G. W.; Galloway, D. A.; Le, T.; Rice, G. G.; Bianco, J. A.; Singer, J. W.; Groudine, M. Int. J. Radiât. Oncol. Biol. Phys. 1996, 36, 1099.
17. Yao, S. L.; Akhtar, A. J.; McKenna, K. A.; Bedi, G. C.; Sirdransky, D.; Mabry, M.; Ravi, S. J.; Collector, M. I.; Jones, R. J.; Sharkis, S. J.; Fuchs, E. J.; Bedi, A. Nature Med. 1996,2, 1140.
18. (e) Bracey, T. S.; Williams, A. C.; Paraskeva, C. Clin. Cancer Res. 1997, 3, 1371.
19. Roberge, M.; Berlinck, R. G. S.; Xu, L.; Andersen, H.; Lim, L.; Curman, D.; Stringer, C. M.; Friend, S. H.; Davies, P.; Vincent, I.; Haggarty, S.; Kelly, M. T.; Britton, R.; Piers, E. Andersen, R. J. Cancer Res. 1998, in press.
20. Vervoort, H. C.; Richards-Gross, S. E.; Fenical, W.; Lee, A. Y.; Clardy, J. J. Org. Chem. 1997, 62, 1486-1490.
21. The structure and synthesis of granulatimide was reported at the 9th International Symposium on Marine Natural Products, Townsville, Australia, July 6-10, 1998.
22. Takahashi, I.; Saitoh, Y.; Yoshida, M.; Sano, H.; Nakano, H.; Morimoto, M.; Tamaoki, T. J. Antibiot. 1989, 42, 571-576.
23. Tamaoki, T.; Noraoto, H.; Takahashi, L; Kato, Y.; Morimoto, M.; Tomita, F. Biochem. Biophys. Res. Commun. 1986,135, 397.
24. Steglich, W.; Stcffan, B.; Kopanski, L.; Eckhardt, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 459.
25. Related condensations of indole-3-acetamide and other mono-substituted acetamides with dialkyl oxalates have been reported. See, for example, (a) Rooney, C. S.; Randall, W. C.; Streeter, K. B.; Zeigler, C.; Cragoe, E. J.; Schwam, H.; Michelson, S. R.; Williams, H. W. R.; Eichler, E.; Duggan, D. E.; Ulm, E. H.; Noll, R. M. J. Med. Chem. 1983, 26, 6, 700.
26. (b) Neel, D. A.; Jirousek, M. R.; McDonald, J. H. Bioorg. Med. Chem. Lett. 1998,8,47.
27. After the work reported herein had been completed and accepted for publication, a paper describing condensations similar to 8 + 9 -10 was published: Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053.
28. For related cyclizations, see (a) Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985,26, 2423.
29. (b) Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 2, 19.
30. Terpin, A.; Winklhofer, C.; Schumann, S.; Steglich, W. Tetrahedron 1998, 54, 1745.
31. For the first total synthesis of a didemnimide (didemnimide C) via a route less convergent than that reported herein for didemnimide A, see ref 12c.
32. Achab, S.; Guyot, M.; Potier, P. J. Am. Chem. Soc. 1978, 100, 3918, and references cited therein.
33. Ohta, S.; Yamamoto, T.; Kawasaki, I.; Yamashita, M.; Katsuma, H.; Nasako, R.; Kobayashi, K.; Ogawa, K. Chem. Pharm. Bull. 1992, 40, 2681.
34. Calculations were performed using HyperChem release 4 for Windows, Polack-Ribiere Alogrithm, in vacuo.
35. See: CRC Handbook of Organic Photochemistry and Photobiology; Harspool, W. M., Ed., CRC Press: New York, 1995; p 513.
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978,43, 2923.