Solid-phase synthesis of dysidiolide-derived protein phosphatase inhibitors

Journal of the American Chemical Society

Volumn 124, Issue 44, 2002, Pages 13171-13178

  Brohm, Dirk ^a,b   Philippe, Nicolas ^a,b   Metzger, Susanne ^a,b   Bhargava, Ajay ^a,b   Müller, Oliver ^a,b   Lieb, Folker ^a,b   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROLYSES;

ADDITION REACTIONS; CELLS; ENZYME INHIBITION; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); TUMORS;

PROTEINS;

DYSIDIOLIDE; NATURAL PRODUCT; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; COMBINATORIAL CHEMISTRY; CYCLOADDITION; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; IC 50; OXIDATION; SOLID;

4-BUTYROLACTONE; CDC25 PHOSPHATASE; CHEMISTRY, ORGANIC; CROSS-LINKING REAGENTS; ENZYME INHIBITORS; SESQUITERPENES; SOLUTIONS;

EID: 0037032265     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027609f     Document Type: Article

References (59)

1. Breinbauer, R.; Vetter, I.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878-2890.
2. Review: Mann, J. Nature Rev. Cancer 2002, 2, 143-148.
3. For reviews on compound library synthesis based on natural products, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (c) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
4. For reviews on compound library synthesis based on natural products, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (c) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
5. For reviews on compound library synthesis based on natural products, see: (a) Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150. (b) Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, Germany, 2002. (c) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145-156.
6. (a) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272.
7. (b) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Finlay, M. R. V.; Giannakakou, P.; Verdierpinard, P.; Hamel, E. Angew. Chem. 1997, 109, 2181-2187; Angew. Chem., Int. Ed. Engl. 1997, 36, 2097-2103.
8. (b) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Finlay, M. R. V.; Giannakakou, P.; Verdierpinard, P.; Hamel, E. Angew. Chem. 1997, 109, 2181-2187; Angew. Chem., Int. Ed. Engl. 1997, 36, 2097-2103.
9. Part of this work was published in preliminary form: Brohm, D.; Metzger, S.; Bhargava, A.; Müller, O.; Lieb, F.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 307-311.
10. Draetta, G.; Eckstein, J. Biochim. Biophys. Acta 1997, 1332 (2), M53-M63.
11. Hoffmann, I.; Draetta, G.; Karsenti, E. EMBO J. 1994, 13, 4302-4310.
12. Nilsson, I.; Hoffmann, I. Prog. Cell Cycle Res. 2000, 4, 107-114.
13. Millar, J. B.; Blewitt, J.; Gerace, L.; Sadku, K.; Featherstone, C.; Russell, P. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10500-10504.
14. Eckstein, J. W. Gene Ther. Mol. Biol. 1998, 1, 707-711.
15. Zhang, Z.-Y. Curr. Opin. Chem. Biol. 2001, 5, 416-423.
16. (a) Cebula, R. E.; Blanchard, J. L.; Boisclair, M. D.; Pal, K.; Bockovich, N. Bioorg. Med. Chem. Lett. 1997, 7, 2015-2020.
17. (b) Dodo, K.; Takahashi, M.; Yamada, Y.; Sugimoto, Y.; Hashimoto, Y.; Shirai, R. Bioorg. Med. Chem. Lett. 2000, 10, 615-617.
18. (c) Peng, H.; Zalkow, L. H. J. Med. Chem. 1998, 41, 4677-4680.
19. (d) Peng, H.; Xie, W.; Kim, D.-I.; Zalkow, L. H.; Powis, G.; Otterness, D. M.; Abraham, R. T. Bioorg. Med. Chem. 2000, 8, 299-306.
20. (e) Peng, H.; Otterness, D. M.; Abraham, R. T.; Zalkow, L. H. Tetrahedron 2001, 57, 1891-1896.
21. Gunasekera, S. P.; McCarthy, P. J.; Kelly-Borges, M.; Lobkovsky, E.; Clardy, J. J. Am. Chem. Soc. 1996, 118, 8759-8760.
22. Danishefsky, S.; Magnuson, S. R.; Rosen, N. Patent WO 99/40079, 1999.
23. (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425-12431.
24. (b) Boukouvalas, J.; Cheng, Y.-X.; Robichaud, J. J. Org. Chem. 1998, 63, 228-229.
25. (c) Magnuson, S. R.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 1615-1616.
26. (d) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111-2114.
27. (e) Jung, M. E.; Nishimura, N. Org. Lett. 2001, 3, 2113-2115.
28. (f) Brohm, D.; Waldmann, H. Tetrahedron Lett. 1998, 39, 3995-3998.
29. (g) Miyaoka, H.; Kajiwara, Y.; Yamada, Y. Tetrahedron Lett. 2000, 41, 911-914.
30. (h) Piers, E.; Caillé, S.; Chen, G. Org. Lett. 2000, 2, 2483-2486.
31. (i) Demeke, D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177-3179.
32. (j) Paczkowski, R.; Maichle-Mössmer, C.; Maier, M. E. Org. Lett. 2000, 2, 3967-3969.
33. (k) Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.; Hashimoto, Y.; Shirai, R. Bioorg. Med. Chem. Lett. 2000, 10, 2571-2574.
34. For the use of traceless linkers based on olefin metathesis see: (a) Peters, J.-U.; Blechert, S. Synlett 1997, 348-350. (b) Knerr, L.; Schmidt, R. R.; Synlett 1999, 1802-1804.
35. For the use of traceless linkers based on olefin metathesis see: (a) Peters, J.-U.; Blechert, S. Synlett 1997, 348-350. (b) Knerr, L.; Schmidt, R. R.; Synlett 1999, 1802-1804.
36. Samu, E.; Huszthy, P.; Somogyi, L.; Hollósi, M. Tetrahedron: Asymmetry 1999, 10, 2775-2795.
37. Gordeev, M. F.; Luehr, G. W.; Hui, C. H.; Gordon, E. M.; Patel, D. V. Tetrahedron 1998, 54, 15879-15890.
38. (a) Nikolaou, K. C.; Winssinger, N.; Vourloumis, D.; Oshima, T.; Kim, S.; Pfefferkorn, J.; Xu, J.-Y.; Li, T. J. Am. Chem. Soc. 1998, 120, 10814-10826.
39. (b) Nikolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272.
40. (c) Nikolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.: Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Ray, M.; Finlay, V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem. 1997, 109, 2181-2187; Angew. Chem., Int. Ed. Engl. 1997, 36, 2097-2103.
41. (c) Nikolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Winssinger, N.; He, Y.; Ninkovic, S.: Sarabia, F.; Vallberg, H.; Roschangar, F.; King, N. P.; Ray, M.; Finlay, V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem. 1997, 109, 2181-2187; Angew. Chem., Int. Ed. Engl. 1997, 36, 2097-2103.
42. (a) Figerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022.
43. (b) Figerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
44. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2197-2181. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
45. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2197-2181. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
46. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
47. Harrity, J. P.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H.; J. Am. Chem. Soc. 1998, 120, 2343-2351.
48. Rutjes, F. P. J. T.; Veerman, J. J. N.: van Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H. Eur. J. Org. Chem. 1998, 2583-2589.
49. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333-9336.
50. Sammakia, T.; Berliner, M. A. J. Org. Chem. 1994, 59, 6890-6891.
51. Okabe, M.; Tamagawa, H.; Tada, M. Synth. Commun. 1983, 13, 373-378.
52. Mateos, A. F.; Lopez-Barba, A. M. J. Org. Chem. 1995, 60, 3580-3585.
53. Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.: Hashimoto, Y.; Shirai, R. Bioorg. Med. Chem. Lett. 2000, 10, 2571-2574.
54. Mosman, T. J. Immunol. Methods 1983, 65, 55-63.
55. Kroeniger, A.; Wheeler, D. M. S. Tetrahedron 1972, 28, 255-266.
56. Kayser, M. M.; Chen, G.; Stewart, J. D. J. Org. Chem. 1998, 63, 7103-7106.
57. Lafontaine, J. A.; Leahy, J. W. Tetrahedron Lett. 1995, 36, 6029-6032.
58. (a) Bartlett, P. D.; Bank, S.: Crawford, R. J.; Schmid, G. H. J. Am. Chem. Soc. 1965, 87, 1288-1297.
59. (b) Wilt, J. W.; Massie, S. N.; Dabek, R. B. J. Org. Chem. 1970, 35, 2803-2806.