Synthesis and biological activity of novel 3'-trifluoromethyl taxoids

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 2, 1997, Pages 133-138

  Ojima, Iwao ^a   Slater, John C ^a   Pera, Paula ^c   Veith, Jean M ^c   Abouabdellah, Ahmed ^b   Bégué, Jean Pierre ^b   Bernacki, Ralph J ^c  

^a STONY BROOK UNIVERSITY   (United States)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031023523     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00595-1     Document Type: Article

References (26)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
2. Guéritte-Voegelein, F.; Mangatal, L.; Guénard, D.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C. Acta Crstallogr. 1990, C46, 781.
3. Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M., Ed.; American Chemical Society: Washington D.C., 1995.
4. Suffness, M. Annual Reports in Medicinal Chemistry; J. A. Bristol, Ed.; Academic: San Diego, 1993; Vol. 28; pp 305-314, Chapter 32.
5. Suffness, M. Taxol: Science and Applications; CRC: New York, 1995.
6. Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Seminars in Oncology 1992, 19, 646.
7. Guénard, D.; Guéritte-Vogelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160.
8. Shiff, P. B.; Fant, J.; Horwitz, S. B. Nature (London) 1979, 277, 665.
9. Horwitz, S. B., Presented at the Stony Brook Symposium on Taxol and Taxotère; 1993, Abstracts 23-24.
10. Ringel, I.; Horwitz, S. B. J. Natl. Cancer Inst. 1991, 83, 288.
11. Verweij, J.; Clavel, M.; Chevalier, B. Ann. Oncol. 1994, 5, 495.
12. Ojima, I.; Kuduk, S. D.; Slater, J. C.; Gimi, R. H.; Sun, C. M. Tetrahedron 1996, 52, 209.
13. Ojima, I.; Kuduk, S. D.; Slater, J. C.; Gimi, R. H.; Sun, C. M.; Chakravarty, S.; Ourevich, M.; Abouabdellah, A.; Bonnet-Delpon, D.; Bégué, J.-P.; Veith, J. M.; Pera, P.; Bernacki, R. J. In Biomedical Frontiers of Fluorine Chemistry".ACS Symp. Ser. 639; I. Ojima; J. R. McCarthy and J. T. Welch, Ed.; American Chemical Society: Washington, D. C., 1996; pp 228-243.
14. Abouabdellah, A.; Bèguè, J.-P.; Bonnet-Delpon, D. Synlett 1996, 399.
15. Denis, J.-N.; Greene, A. E.; Guénard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917.
16. Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543.
17. Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1996, 39, 3889.
18. Holton, R. A.; Biediger, R. J., U.S. Patent 5,243,045, 1993.
19. Holton, R. A.; Biediger, R. J.; Boatman, P. D. In Taxol®: Science and Applications; M. Suffness, Ed.; CRC: New York, 1995; pp 97-121.
20. Skehan, P.; Streng, R.; Scudierok, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107.
21. Sikic, B. I. J. Clin. Oncol. 1993, 11, 1629.
22. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 115, 11650.
23. Paloma, L. G.; Guy, R. K.; Wrasidlo, W.; Nicolaou, K. C. Chem. Biol. 1994, 2, 107.
24. Hilton, B. D.; Chmurny, G. N.; Muschik, G. M. J. Nat. Prod. 1992, 55, 1157.
25. Falzone, C. J.; Benesi, A. J.; Lecomte, J. T. Tetrahedron Lett. 1992, 33, 1169.
26. Baker, J. K. Spectroscopy Lett. 1992, 25, 31.