C-15 thiazol-4-yl analogues of (E)-9,10-didehydroepothilone D: Synthesis and cytotoxicity

Organic Letters

Volumn 8, Issue 14, 2006, Pages 3057-3059

  Hearn, Brian R ^a   Zhang, Dan ^a   Li, Yong ^a   Myles, David C ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9,10 DEHYDROEPOTHILONE D; 9,10-DEHYDROEPOTHILONE D; ANTINEOPLASTIC AGENT; EPOTHILONE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG RESISTANCE; DRUG SCREENING; HUMAN; IC 50; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; EPOTHILONES; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; THIAZOLES;

EID: 33746581932     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061087h     Document Type: Article

References (19)

1. (a) Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567.
2. (b) Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560.
3. Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325.
4. For review, see: Altmann, K.-H. Curr. Pharm. Des. 2005, 11, 1595.
5. For information regarding human clinical trials of epothilone D (KOS 862) and (E)-9,10-didehydroepothilone D (KOS 1584), visit: www.kosan.com.
6. (a) Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Tong, W. P.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 2899.
7. (b) Yoshimura, F.; Rivkin, A.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Sukenick, G.; Morel, F. F.; Taylor, R. E.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 2518.
8. (a) Chou, T.-C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 4762.
9. (b) Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
10. Dong, S. D.; Sundermann, K.; Smith, K. M. J.; Petryka, J.; Liu, F.; Myles, D. C. Tetrahedron Lett. 2004, 45, 1945.
11. (a) Altmann, K.-H.; Bold, G.; Caravatti, G.; Flörsheimer, A.; Guagnano, V.; Wartmann, M. Bioorg. Med. Chem. Lett. 2000, 10, 2765.
12. (b) Cachoux, F.; Isarno, T.; Wartmann, M.; Altmann, K.-H. Angew. Chem., Int. Ed. 2005, 44, 7469.
13. C-15-(2-Methylthiazol-4-yl)epothilone D is a known compound with micromolar cytotoxicity: Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093.
14. Nicolaou, K. C.; Scarpelli, R.; Bollbuck, B.; Werschkun, B.; Pereira, M. M. A.; Wartmann, M.; Altmann, K.-H.; Zaharevitz, D.; Gussio, R.; Giannakakou, P. Chem. Biol. 2000, 7, 593.
15. For more recent work, see: (a) Bold, G.; Wojeik, S.; Caravatti, G.; Lindauer, R.; Stierlin, C.; Gertsch, J.; Wartmann, M.; Altmann, K.-H. ChemMedChem 2006, 1, 37.
16. (b) Nicolaou, K. C.; Pratt, B. A.; Arseniyadis, S.; Wartmann, M.; O'Brate, A.; Giannakakou, P. ChemMedChem 2006, 1, 41.
17. Nettles, J. H.; Li, H.; Cornett, B.; Krahn, J. M.; Snyder, J. P.; Downing, K. H. Science 2004, 305, 866.
18. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
19. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.