Design and Total Synthesis of a Superior Family of Epothilone Analogues, which Eliminate Xenograft Tumors to a Nonrelapsable State

Angewandte Chemie - International Edition

Volumn 42, Issue 39, 2003, Pages 4762-4767

  Chou, Ting Chao ^a,b   Dong, Huajin ^a,b   Rivkin, Alexey ^a   Yoshimura, Fumihiko ^a   Gabarda, Ana E ^a   Cho, Young Shin ^a   Tong, William P ^a   Danishefsky, Samuel J ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Antitumor agents; Conformation analysis; Epothilones; Natural products; Structure activity relationships

Indexed keywords

DRUG DOSAGE; SYNTHESIS (CHEMICAL); TUMORS;

TUMOR SHRINKAGE;

ORGANIC COMPOUNDS;

12,13 DESOXYEPOTHILONE; 26 TRIFLUORO 9,10 DEHYDROEPOTHILONE B; 9,10 DEHYDRO 26 TRIFLUOROEPOTHILONE DERIVATIVE; DOCETAXEL; EPOTHILONE B; EPOTHILONE DERIVATIVE; PACLITAXEL; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT;

ARTICLE; BODY WEIGHT; CANCER INHIBITION; CONVALESCENCE; DOSE RESPONSE; DRUG SYNTHESIS; DRUG TOLERABILITY; GROWTH INHIBITION; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; NUDE MOUSE; RELAPSE; REMISSION; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH; XENOGRAFT; ANIMAL; CANCER TRANSPLANTATION; CELL CULTURE; CHEMICAL MODEL; DRUG SCREENING; HUMAN; METABOLISM; NEOPLASM; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; BODY WEIGHT; DRUG SCREENING ASSAYS, ANTITUMOR; EPOTHILONES; HUMANS; MICE; MICE, NUDE; MODELS, CHEMICAL; NEOPLASM TRANSPLANTATION; NEOPLASMS; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 1542541269     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352361     Document Type: Article

References (32)

1. G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach (GBF), DE-B 4138042, 1993.
2. G. Höfle, N. Bedorf, H. Steinmetz, D. Schumburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
3. G. Höfle, N. Bedorf, H. Steinmetz, D. Schumburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
4. K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1996, 49, 560.
5. K. C. Nicolaou, A. Ritzén, K. Namoto, Chem. Commun. 2001, 17, 1523.
6. K. H. Altmann, M. Wartmann, T. O'Reilly, Biochim. Biophys. Acta 2000, 1470, M79.
7. C. R. Harris, S. J. Danishefsky, J. Org. Chem. 1999, 64, 8434.
8. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120; Angew. Chem. Int. Ed. 1998, 37, 2014.
9. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120; Angew. Chem. Int. Ed. 1998, 37, 2014.
10. G. A. Orr, S. B. Horwitz, Drug Discovery Today 2001, 6, 1153.
11. D. M. Bollag, P. A. Mcqueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods, Cancer Res. 1995, 55, 2325.
12. T.-C. Chou, X. G. Zhang, C. R. Harris, S. D. Kuduk, A. Balog, K. A. Savin, J. R. Bertino, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 9642.
13. For more information about clinical trials of dEpoB, visit: www.kosan.com.
14. D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 2178; Angew. Chem. Int. Ed. Engl. 1997, 36, 2093.
15. D.-S. Su, A. Balog, D. Meng, P. Bertinato, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 2178; Angew. Chem. Int. Ed. Engl. 1997, 36, 2093.
16. C. R. Harris, S. D. Kuduk, A. Balog, K. Savin, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 7050.
17. D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, J. Am. Chem. Soc. 1997, 119, 10073.
18. T.-C. Chou, X. G. Zhang, C. R. Harris, S. D. Kuduk, A. Balog, K. A. Savin, J. R. Bertino, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 15798.
19. A. Rivkin, F. Yoshimura, A. E. Gabarda, T.-C. Chou, H. Dong, W. P. Tong, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 2899.
20. B. E. Smart, J. Fluorine Chem. 2001, 109, 3.
21. J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407.
22. F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622; Angew. Chem. Int. Ed. 2003, 42, 2518.
23. F. Yoshimura, A. Rivkin, A. E. Gabarda, T.-C. Chou, H. Dong, G. Sukenick, F. F. Morel, R. E. Taylor, S. J. Danishefsky, Angew. Chem. 2003, 115, 2622; Angew. Chem. Int. Ed. 2003, 42, 2518.
24. A. Rivkin, J. T. Njardarson, K. Biswas, T.-C. Chou, S. J. Danishefsky, J. Org. Chem. 2002, 67, 7737.
25. R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856.
26. R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446.
27. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18.
28. Alkene Metathesis in Organic Chemistry (Ed.: A. Fürstner), Springer, Berlin, 1998.
29. A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
30. A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012.
31. R. R. Schrock, Top. Organomet. Chem. 1998, 1, 1.
32. T.-C. Chou, O. A. O'Connor, W. P. Tong, Y. Guan, Z.-G. Zhang, S. J. Stachel, C. Lee, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 2001, 98, 8113-8118.