Syntheses and biological activity of C-3'-difluoromethyl-taxoids

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 7, 2000, Pages 1619-1628

  Ojima, Iwao ^a   Lin, Songnian ^a   Slater, John C ^a   Wang, Tao ^a   Pera, Paula ^b   Bernacki, Ralph J ^b   Ferlini, Cristiano ^c   Scambia, Giovanni ^c  

^a STONY BROOK UNIVERSITY   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

^c CATHOLIC UNIVERSITY   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DNA FRAGMENT; DOCETAXEL; PACLITAXEL; TAXOID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG RESISTANCE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CELL DIVISION; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, NEOPLASM; FLOW CYTOMETRY; HUMANS; INHIBITORY CONCENTRATION 50; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TUMOR CELLS, CULTURED;

EID: 0033948409     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00093-6     Document Type: Article

References (47)

1. Wani M.C., Taylor H.L., Wall M.E., Coggon P., McPhail A.T. J. Am. Chem. Soc. 93:1971;2325.
2. Guéritte-Voegelein F., Mangatal L., Guénard D., Potier P., Guilhem J., Cesario M., Pascard C. Acta Crystall. C46:1990;781.
3. Rowinsky E.K., Onetto N., Canetta R.M., Arbuck S.G. Seminars in Oncology. 19:1992;646.
4. Guénard D., Guéritte-Vogelein F., Potier P. Acc. Chem. Res. 26:1993;160.
5. Suffness, M. In Annual Reports in Medicinal Chemistry; J. A. Bristol, Ed.; Academic: San Diego, 1993; Vol. 28; Chapter 32, pp. 305-314.
6. Suffness M. Taxol: Science and Applications. 1995;CRC Press, New York.
7. Georg G.I., Chen T.T., Ojima I., Vyas D.M. Taxane Anticancer Agents: Basic Science and Current Status. 1995;American Chemical Society, Washington, DC.
8. Kingston, D. G. I. In Taxane Anticancer Agents: Basic Science and Current Status; ACS Symp. Ser. 583; G. I. Georg; T. T. Chen; I. Ojima and D. M. Vyas, Eds.; American Chemical Society: Washington, DC, 1995; pp 203-216.
9. Holton, R. A.; Biediger, R. J.; Boatman, P. D. In Taxol®: Science and Applications; M. Suffness, Ed.; CRC Press: New York, 1995; pp 97-121.
10. Boge, T. C.; Georg, G. I. In Enantioselective Synthesis of β-Amino Acids; E. Juaristi, Ed.; Wiley-VCH: New York, 1997; pp 1-43.
11. Ojima, I.; Kuduk, S. D.; Chakravarty, S. In Adv. Med. Chem.; B. E. Maryanoff and A. B. Reitz, Eds.; JAI Press: Greenwich, CT, 1998; Vol. 4, pp 69-124.
12. Ojima I., Lin S., Wang T. Curr. Med. Chem. 6:1999;927.
13. Schiff P.B., Fant J., Horwitz S.B. Nature. 277:1979;665.
14. Horwitz, S. B. In Stony Brook Symposium on Taxol and Taxotère; Stony Brook: NY, 14-15 May 1993; Abstracts 23-24.
15. Arbuck, S. G.; Blaylock, B. A. In Taxol®: Science and Applications; M. Suffness, Ed.; CRC Press: Boca Raton, 1995; pp 379-415.
16. Verweij J., Clavel M., Chevalier B. Ann. Oncol. 5:1994;495-505.
17. Seidman, A. D. In Stony Brook Symposium on Taxol and Taxotère; Stony Brook, NY, 14-15 May 1993; Abstracts pp 14-16.
18. Ojima I., Kuduk S.D., Slater J.C., Gimi R.H., Sun C.M. Tetrahedron. 52:1996;209.
19. Cresteil T., Monsarrat B., Alvinerie P., Tréluyer J.M., Vieira I., Wright M. Cancer Res. 54:1994;386.
20. Vuilhorgne, M.; Gaillard, C.; Sanderlink, G. J.; Royer, I.; Monsarrat, B.; Dubois, J.; Wright, M. In Taxane Anticancer Agents: Basic Science and Current Status. American Chemical Society: Washington, DC, 1995; pp 98-110.
21. Ojima I., Inoue T., Chakravarty S. J. Fluorine Chem. 97:1999;3.
22. 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, Eds.; American Chemical Society: Washington, DC, 1996; pp 228-243.
23. Ojima I., Kuduk S.D., Chakravarty S., Ourevitch M., Bégué J.-P. J. Am. Chem. Soc. 119:1997;5519.
24. Ojima, I.; Inoue, T.; Slater, J. C.; Lin, S.; Kuduk, S. C.; Chakravarty, S.; Walsh, J. J.; Gilchrist, L.; McDermott, A. E.; Cresteil, T.; Monsarrat, B.; Pera, P.; Bernacki, R. J. In Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions; ACS Symp. Ser. 746; Ramachandran, Ed.; American Chemical Society: Washington, DC, 1999; Chapter 12.
25. Kant J., Huang S., Wong H., Fairchild C., Vyas D., Farina V. Bioorg. Med. Chem. Lett. 3:1993;2471.
26. Chen S.-H., Huang S., Farina V. Tetrahedron Lett. 35:1994;41.
27. Chen S.-H., Kadow J.F., Farina V., Fairchild C.R., Johnston K.A. J. Org. Chem. 59:1994;6156.
28. Chen S.H., Kant J., Mamber S.W., Roth G.P., Wei J., Marshall D., Vyas D., Farina V. Bioorg. Med. Chem. Lett. 4:1994;2223.
29. Chen S.-H., Wei J.-M., Long B.H., Fairchild C.A., Carboni J., Mamber S.W., Rose W.C., Johnston K., Casazza A.M., Kadow J.F., Farina V., Vyas D.M., Doyle T.W. Bioorg. Med. Chem. Lett. 5:1995;2741.
30. Ojima I., Habus I., Zhao M., Zucco M., Park Y.H., Sun C.-M., Brigaud T. Tetrahedron. 48:1992;6985.
31. Denis J.-N., Greene A.E., Guénard D., Guéritte-Voegelein F., Mangatal L., Potier P.A. J. Am. Chem. Soc. 110:1988;5917.
32. 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. 35:1994;5543.
33. 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. 39:1996;3889.
34. Ojima I., Slater J.S., 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. 40:1997;267.
35. Ojima I., Duclos O., Kuduk S.D., Sun C.-M., Slater J.C., Lavelle F., Veith J.M., Bernacki R.J. Bioorg. Med. Chem. Lett. 4:1994;2631.
36. Ojima I., Lin S. J. Org. Chem. 63:1998;224.
37. Ojima I., Lin S., Chakravarty S., Fenoglio I., Park Y.H., Sun C., Appendino G., Pera P., Veith J.M., Bernacki R.J. J. Org. Chem. 63:1998;1637.
38. Puech, F.; Gosselin, G.; Imbach, J.-L. J. Chem. Soc., Chem. Commun. 1989, 955.
39. Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. In Taxol®: Science and Applications; M. Suffness, Ed.; CRC Press: New York, 1995; pp 317-375.
40. 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. 82:1990;1107.
41. Ireland C.M., Pittman S.M. Biochem. Pharmacol. 49:1995;1491.
42. Darzynkiewicz Z., Bruno S., Del Bino G., Gorczyca W., Hotz M.A., Lassota P., Traganos F. Cytometry. 13:1992;795.
43. Distefano M., Scambia G., Ferlini C., Gaggini C., Vincenzo R.D., Riva A., Bombardelli E., Ojima I., Fattorossi A., Panici P.B., Mancuso S. Int. J. Cancer. 72:1997;844-850.
44. Holford N.H.G., Scheiner L.B. Clin. Pharmaco. 6:1981;429.
45. Marquardt, D. W. J. Soc. Ind. Appl. Math. 1963, 11, 431.
46. Nash J.C. Compact Numerical Method for Computers: Linear Algebra and Function Minimisation. 1979;John Wiley & Sons, New York.
47. Scambia, G.; Ranelletti, F.O.; Benedetti Panici, P.; De Vincenzo, R.; Bonanno, G.; Ferranadina, G.; Piantelli, M.; Bussa, S.; Rumi, C.; Cianfriglia, P.; Mancuso, S. Cancer Chemother. Pharmacol. 1994, 459.