Synthesis of enatiopure fluorine-containing taxoids and their use as anticancer agents as well as probes for biomedical problems

ACS Symposium Series

Volumn 746, Issue , 1999, Pages 158-181

  Ojima, Iwao ^a   Inoue, Tadashi ^a   Slater, John C ^a   Lin, Songnian ^a   Kuduk, Scott D ^a   Chakravarty, Subrata ^a   Walsh, John J ^a   Cresteil, Thierry ^b   Monsarrat, Bernard ^b   Pera, Paula ^c   Bernacki, Ralph J ^c  

^a STONY BROOK UNIVERSITY   (United States)

^b Lab Pharmacologie Toxicologie F   (France)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041910150     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2000-0746.ch012     Document Type: Article

References (36)

1. Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents: Basic Science and Current Status; American Chemical Society: Washington D.C., 1995.
2. Suffness, M. Taxol: Science and Applications; CRC Press: New York, 1995.
3. Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G., "Taxol: The First of the Taxanes, and Important New Class of Antitumor Agents", Seminars in Oncology 1992, 19, 646-662.
4. Rowinsky, E. K., Ann. Rev. Med. 1997, 48, 353-374.
5. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T., J. Am. Chem. Soc. 1971, 93, 2325-2327.
6. Guénard, D.; Guéritte-Vogelein, F.; Potier, P., Acc. Chem. Res. 1993, 26, 160-167.
7. Shiff, P. B.; Fant, J.; Horwitz, S. B., Nature 1979, 277, 665-667.
8. Shiff, P. B.; Horwitz, S. B Proc. Natl. Acad. Sci., U. S. A. 1980, 77, 1561-1565.
9. Vallee, R. B., Taxol®: Science and Applications; M. Suffness, Ed.; CRC Press: New York, 1995; pp 259-274.
10. Ringel, I.; Horwitz, S. B., J. Natl. Cancer Inst. 1991, 83, 288-291.
11. Vuilhorgne, M.; Gaillard, C.; Sanderlink, G. J.; Royer, I.; Monsarrat, B.; Dubois, J.; Wright, M., Taxane Anticancer Agents: Basic Science and Current Status; ACS Symp. Series 583; G. I. Georg; T. T. Chen; I. Ojima and D. M. Vyas, Ed.; American Chemical Society: Washington D. C., 1995; pp 98-110.
12. Monsarrat, B.; Mariel, E.; Cros, S.; Garès, M.; Guénard, D.; Guéritte-Voegelein, F.; Wright, M., Drug Metab. Dispos. 1990, 18, 895-901.
13. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993; Vol. 48.
14. Ojima, I.; Kuduk, S. D.; Slater, J. C.; Gimi, R. H.; Sun, C. M., Tetrahedron 1996, 52, 209-224.
15. Ojima, I.; Slater, J. C.; Pera, P.; Veith, J. M.; Abouabdellah, A.; Bégué, J.-P.; Bernacki, R. J., Bioorg. Med. Chem. Lett. 1997, 7, 209-214.
16. Ojima, I.; Kuduk, S. D.; Chakravarty, S.; Ourevitch, M.; Bégué, J.-P., J. Am. Chem. Soc. 1997, 119, 5519-5527.
17. Gilchrist, L.; McDermott, A. E.; Ojima, I.; Kuduk, S. D.; Inoue. T.; Lin, S.; Walsh, J. J.; Chakravarty, S.; Nakanishi, K.; Orr, G.; Horwitz, S. B., 1997, unpublished results.
18. Chen, S.-H.; Farina, V.; Wei, J.-M; Long, B.; Fairchild, C.; Mamber, S. W.; Kadow, J. F.; Vyas, D.; Doyle, T. W., Bioorg. Med. Chem. Lett. 1994, 4, 479-482.
19. Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H., J. Am. Chem. Soc. 1994, 116, 1597-1598.
20. Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J., J. Med. Chem. 1994, 37, 1408-1410.
21. Ojima, I.; Fenoglio, I.; Park, Y. H.; Pera, P.; Bernacki, R. J., Bioorg. Med. Chem. Lett. 1994, 4, 1571-1576.
22. Ojima, I.; Fenoglio, I.; Park, Y. H.; Sun, C.-M.; Appendino, G.; Pera, P.; Bernacki, R. J., J. Org. Chem. 1994, 59, 515-517.
23. Chaudhary, A. G., Gharpure, M. M.; Rimoldi, J. M.; Chordia, M. D.; Gunatilaka, A. A. L.; Kingston, D. G. I., J. Am. Chem. Soc. 1994, 116, 4097-4098.
24. 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, 1107-1112.
25. Monsarrat, B.; Royer, I.; Wright, M.; Cresteil, T., Bull Cancer 1997, 84, 125-133.
26. Ojima, I.; Slater, J. C., Chirality 1997, 9, 487-494.
27. Ojima, I.; Slater, J. C.; Kuduk, S. D.; Takeuchi, C. S.; Gimi, R. H.; Sun, C.-M.; Park, Y. H.; Pera, P.; Veith, J. M.; Bernacki, R. J. J. Med. Chem. 1997, 40, 267-278.
28. Georg, G. I.; Harriman, G. C. B.; Vander Velde, D. G.; Boge, T. C.; Cheruvallath, Z. S.; Datta, A.; Hepperle, M.; Park, H.; Himes, R. H.; Jayasinghe, L., Taxane Anticancer Agents: Basic Science and Current Status; G. I. Georg; T. T. Chen; I. Ojima and D. M. Vyas, Ed.; ACS Symp. Series 583;American Chemical Society: Washington D.C., 1995; pp 217-232.
29. Guéritte-Voegelein, F.; Mangatal, L.; Guénard, D.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C., Acta Crstallogr. 1990, C46, 781-784.
30. Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krauss, N. E., Can. J. Chem. 1994, 252-260.
31. Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; Francl, M. M.; Heerding, J. M.; Krauss, N. E., Tetrahedron 1993, 49, 6545-6560.
32. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A., J. Am. Chem. Soc. 1993, 115, 11650-11651.
33. Mastropaolo, D.; Camerman, A.; Luo, Y.; Brayer, G. D.; Camerman, N., "X-ray Structure of Paclitaxel", Proc. Natl. Acad. Sci. USA 1995, 92, 6920-6924.
34. Paloma, L. G.; Guy, R. K.; Wrasidlo, W.; Nicolaou, K. C., Chem. Biol. 1994, 2, 107-112.
35. Chakravarty, S.; Ojima, I., The 214th American Chemical Society National Meeting, Las Vegas, September 8-12, 1997, Abstracts, MEDI 075.
36. Ojima, I., 7th International Kyoto Conference on Organic Chemistry, Kyoto, Japan, November 10-14, 1991, Abstracts, IL-19.