Unexpectedly Facile Hydrolysis of the 2-Benzoate Group of Taxol and Syntheses of Analogs with Increased Activities

Journal of the American Chemical Society

Volumn 116, Issue 9, 1994, Pages 4097-4098

  Chaudhary, Ashok G ^a   Gharpure, Milind M ^a   Rimoldi, John M ^a   Chordia, Mahendra D ^a   Gunatilaka, A A Leslie ^a   Kingston, David G I ^a   Grover, Surinder ^b   Lin, Chii M ^b   Hamel, Ernest ^b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL; TAXANE DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; NONHUMAN; PROTEIN POLYMERIZATION; REACTION ANALYSIS; TUMOR CELL;

EID: 0028235069     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00088a063     Document Type: Article

References (17)

1. Wani, M.C., Taylor, H.L., Wall, M.E., Coggon, P., McPhail, A.T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. Rowinsky, E.K., Onetto, N., Canetta, R.M., Arbuck, S.G. Sem. Oncol. 1992, 19, 646-662.
3. Slichenmyer, W.J., Von Hoff, D.D. Anti-Cancer Drugs 1991, 2, 519-530.
4. Kingston, D.G.I. Pharmacol. Ther., 1991, 52, 1-35.
5. Kingston, D.G.I., Molinero, A.A., Rimoldi, J.M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., Tamm, Ch., Eds., Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206.
6. Guénard, D., Guéritte-Voegelein, F., Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
7. Miller, R.W., Powell, R.G., Smith, C.R., Jr., Arnold, E., Clardy, J. J. Org. Chem. 1981, 46, 1469-1474.
8. Ringel, I., Horwitz, S.B.J. Pharmacol. Exp. Ther. 1987, 242, 692-698.
9. Farina, V., Huang, S. Tetrahedron Lett. 1993, 33, 3979-3982.
10. Samaranayake, G., Neidigh, K.A., Kingston, D.G.I. J. Nat. Prod. 1993, 56, 884-898.
11. Chen, S.-H., Wei, J.-M., Farina, V. Tetrahedron Lett. 1993, 34, 3205-3206.
12. Wahl, A., Guéritte-Voegelein, F., Guénard, D., Le Goff, M.-T., Potier, P. Tetrahedron 1992, 48, 6965-6974.
13. 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.
14. Vander Velde, D.G., Georg, G.I., Grünewald, G.L., Gunn, C.W., Mitscher, L.A. J. Am. Chem. Soc. 1993, 115, 11650-11651.
15. Rimoldi, J.M., Kingston, D.G.I., Chaudhary, A.G., Samaranayake, G., Grover, S., Hamel, E. J. Nat. Prod. 1993, 56, 1313-1330.
16. Lataste, H., Senilh, V., Wright, M., Guénard, D., Potier, P. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 4090-4094.
17. Dubois, J., Guénard, D., Guéritte-Voegelein, F., Guedira, N., Potier, P., Gillet, B., Beloeil, J.-C. Tetrahedron 1993, 49, 6533-6544.