Molecular design and chemical synthesis of a highly potent epothilone

ChemMedChem

Volumn 1, Issue 1, 2006, Pages 41-44

  Nicolaou, K C ^a,b   Pratt, Benjamin A ^a,b   Arseniyadis, Stellios ^a,b   Wartmann, Markus ^c   O'Brate, Aurora ^d   Giannakakou, Paraskevi ^d  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c NOVARTIS PHARMA AG   (Switzerland)

^d EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Analogues; Antitumor agents; Epothilones; Molecular design; Synthesis design

Indexed keywords

EPOTHILONE DERIVATIVE;

ARTICLE; CHEMISTRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EPOTHILONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33745405004     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200500056     Document Type: Article

References (36)

1. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671-1673;
2. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
3. Reviews: a) K.-H. Altmann, Org. Biomol. Chem. 2004, 2, 2137-2152;
4. b) E. B. Watkins, A. G. Chittiboyina, J.-C. Jung, M. A. Avery, Curr. Pharm. Des. 2005, 11, 1615-1653;
5. c) K. C. Nicolaou, A. Ritzén, K. Namoto, Chem. Commun. 2001, 1523-1535;
6. d) K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, Pure Appl. Chem. 1999, 71, 989-997;
7. e) C. R. Harris, S. J. Danishefsky, J. Org. Chem. 1999, 64, 8434-8456;
8. f) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120-2153;
9. Angew. Chem. Int. Ed. 1998, 37, 2014-2045.
10. a) S. Okuno, W. J. Maples, M. R. Mahoney, T. Fitch, J. Stewart, P. M. Fracasso, M. Kraut, D. S. Ettinger, F. Dawkins, C. Erlichman, J. Clin. Oncol. 2005, 23, 3069-3073;
11. b) K.-H. Altmann, Curr. Pharm. Des. 2005, 11, 1595-1613;
12. c) A. Rivkin, T.-C. Chou, S. J. Danishefsky, Angew. Chem. 2005, 117, 2898-2910;
13. Angew. Chem. Int. Ed. 2005, 44, 2838-2850;
14. d) A. Kolman, Curr. Opin. Invest. Drugs 2004, 5, 1292-1297;
15. e) A. Kolman, Curr. Opin. Invest. Drugs 2004, 5, 657-667;
16. f) C. M. Galmarini, C. Dumontet, /Drugs 2003, 6, 1182-1187;
17. g) K. Biswas, H. Lin, J. T. Njardarson, M. D. Chappell, T.-C. Chou, Y. Guan, W. P. Tong, L. He, S. B. Horwitz, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 9825-9832.
18. a) R. M. Buey, J. M. Andreu, A. O'Brate, P. Giannakakou, K. C. Nicolaou, P. K. Sasmal, K. Namoto, Chem. Biol. 2004, 11, 225-236;
19. b) K. C. Nicolaou, P. K. Sasmal, G. Rassias, M. V. Reddy, A. O'Brate, P. Giannakakou, Angew. Chem. 2003, 115, 3639-3644;
20. Angew. Chem. Int. Ed. 2003, 42, 3515-3520;
21. c) K. C. Nicolaou, A. Ritzén, K. Namoto, R. M. Buey, J. F. Díaz, J. M. Andreu, M. Wartmann, K.-H. Altmann, A. O'Brate, P. Giannakakou, Tetrahedron 2002, 58, 6413-6432;
22. d) K. C. Nicolaou, K. Namoto, A. Ritzén, T. Ulven, M. Shoji, J. Li, G. D'Amico, D. Liotta, C. F. French, M. Wartmann, K.-H. Altmann, P. Giannakakou, J. Am. Chem. Soc. 2001, 123, 9313-9323;
23. e) K. C. Nicolaou, R. Scarpelli, B. Bollbuck, B. Werschkun, M. M. A. Pereira, M. Wartmann, K.-H. Altmann, D. Zaharevitz, R. Gussio, P. Giannakakou, Chem. Biol. 2000, 7, 593-599.
24. a) J. H. Nettles, H. Li, B. Cornett, J. M. Krahn, J. P. Snyder, K. H. Kowning, Science 2004, 305, 866-869;
25. b) D. H. Heinz, W.-D. Schubert, G. Höfle, Angew. Chem. 2005, 117, 1324-1327;
26. Angew. Chem. Int. Ed. 2005, 44, 1298-1301.
27. T. Sakamoto, F. Shiga, D. Uchiyama, Y. Kondo, H. Yamanaka, Heterocycles 1992, 33, 813-818.
28. K. Kato, H. Hayakawa, H. Tanaka, H. Kumamoto, S. Shindoh, S. Shuto, T. Miyasaka, J. Org. Chem. 1997, 62, 6833-6841.
29. K. C. Molloy, P. C.; Waterfield, M. F. Mahon, J. Organomet. Chem. 1989, 365, 61-73.
30. B. C. Bookser, Tetrahedron Lett. 2000, 41, 2805-2809.
31. K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, R. Scarpelli, M. M. A. Pereira, B. Bollbuck, A. Bigot, B. Werschkun, N. Winssinger, Chem. Eur. J. 2000, 6, 2783-2800.
32. P. Giannakakou, D. L. Sackett, Y.-K. Kang, Z. Zhan, J. Regis, T. Fojo, M. Poruchynsky, J. Biol. Chem. 1997, 272, 17118-17125.
33. P. Giannakakou, R. Gussio, E. Nogales, K. H. Downing, D. Zaharevitz, B. Bollbuck, G. Poy, D. Sackett, K. C. Nicolaou, T. Fojo, Proc. Natl. Acad. Sci. USA 2000, 97, 2904-2909.
34. For a potent imidazole-containing epothilone B analogue, see: K.-H. Altmann, G. Bold, G. Caravatti, A. Flörsheimer, V. Guagnano, M. Wartmann, Bioorg. Med. Chem. Lett. 2000, 10, 2765-2768.
35. Other notable clinical candidates from the epothilone class include those synthesized by Danishefsky (EpoD/KOS-862, Ref. [2e]; Epo-490, Ref. [3g]; Fludelone, Ref. [3c]), Bristol-Myers Squibb (BMS247550/lactam EpoB, Ref. [3a]; BMS310705/C-20 aminomethyl EpoB, Ref. [3d]), and Schering AG (ZK-EPO, Schering AG press release).
36. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107-1112.