Synthesis and biological evaluation of 1-deoxypaclitaxel analogues

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1814-1822

  Kingston, David G I ^a   Chordia, Mahendra D ^a   Jagtap, Prakash G ^a   Liang, Jingyu ^b   Shen, Ya Ching ^c   Long, Byron H ^d   Fairchild, Craig R ^d   Johnston, Kathy A ^d  

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

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^d BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYPACLITAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; DEACYLATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 0033583279     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981406l     Document Type: Article

References (52)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. (a) Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665-667.
3. (b) Manfredi, J. J.; Horwitz, S. B. Pharmacol. Ther. 1984, 25, 83-125.
4. (a) Arbuck, S. G.; Blaylock, B. A. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 379-415.
5. (b) Holmes, F. A.; Kudelka, A. P.; Kavanagh, J. J.; Huber, M. H.; Ajani, J. A.; Valero, V. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1994; ACS Symposium Series Vol. 583; pp 31-57.
6. (c) Donehower, R. C.; Rowinsky, E. K. Cancer Treat. Rev. 1993, 19 Suppl. C, 63-78.
7. (d) Rowinsky, E. K.; Donehower, R. C. Paclitaxel (Taxol). New Engl. J. Med. 1995, 1004-1014.
8. The early history of the development of paclitaxel has been reviewed by its discoverers: Wall, M. E.; Wani, M. C. In Economic and Medicinal Plant Research; Wagner, H., Farnsworth, N. R., Eds.; Academic Press: Ltd.: London, 1994; Vol. 6, pp 299-322.
9. (a) Chen, S.-H.; Farina, V. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I. and, Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1994; ACS Symposium Series Vol. 583; pp 247-261.
10. (b) 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; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 317-375.
11. (c) Kingston, D. G. I. Pharmacol. Ther. 1991, 52, 1-34.
12. (d) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227.
13. (e) Kingston, D. G. I. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1994; ACS Symposium Series Vol. 583; pp 203-216.
14. (f) Kingston, D. G. I. In Paclitaxel in Cancer Treatment; McGuire, W. P., Rowinsky, E. K., Eds.; Marcel Dekker: New York, Basel, Hong Kong, 1995; Vol. 8, pp 1-33.
15. (g) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
16. Samaranayake, G.; Magri, N. F.; Jitrangsri, C.; Kingston, D. G. I. J. Org. Chem. 1991, 56, 5114-5119.
17. Neidigh, K. A.; Gharpure, M. M.; Rimoldi, J. M.; Kingston, D. G. I.; Jiang, Y. Q.; Hamel, E. Tetrahedron Lett. 1994, 35, 6839-6842.
18. (b) Chordia, M. D.; Chaudhary, A. G.; Kingston, D. G. I.; Jiang, Y. Q.; Hamel, E. Tetrahedron Lett. 1994, 35, 6843-6846.
19. (c) Datta, A.; Jayasinghe, L. R.; Georg, G. I. J. Med. Chem. 1994, 37, 4258-260.
20. (a) Chen, S.-H.; Kadow, J. F.; Farina, V.; Fairchild, C. R.; Johnston, K. A. J. Org. Chem. 1994, 59, 6156-6158.
21. (b) Chen, S.-H.; Fairchild, C.; Long, B. H. J. Med. Chem. 1995, 38, 2263-2267.
22. (c) 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.; Doyle, T. W. Bioorg. Med. Chem. Lett. 1995, 5, 2741-2746.
23. (d) Georg, G. I.; Ali, S. M.; Boge, T. C.; Data, A.; Falborg, L.; Himes, R. H. Tetrahedron Lett. 1994, 35, 8931-8934.
24. Chaudhary, A. G.; Chordia, M. D.; Kingston, D. G. I. J. Org. Chem. 1995, 60, 3260-3262.
25. Chen, S.-H.; Wei, J.-M.; Farina, V. Tetrahedron Lett. 1993, 34, 3205-3206.
26. (a) Chaudhary, A. G.; Rimoldi, J. M.; Kingston, D. G. I. J. Org. Chem. 1993, 58, 3798-3799.
27. (b) Chen, S.-H.; Huang, S.; Kant, J.; Fairchild, C.; Wei, J.; Farina, V. J. Org. Chem. 1993, 58, 5028-5029.
28. (a) Chaudhary, A. G.; Kingston, D. G. I. Tetrahedron Lett. 1993, 34, 4921-4924.
29. (b) Chen, S.-H.; Fairchild, C.; Mamber, S. W.; Farina, V. J. Org. Chem. 1993, 58, 2927-2928.
30. (c) Chen, S. H.; Wei, J. M.; Vyas, D. M.; Doyle, T. W.; Farina, V. Tetrahedron Lett. 1993, 34, 6845-6848.
31. (d) Georg, G. I.; Cheruvallath, Z. S. J. Org. Chem. 1994, 59, 4015-4018.
32. (e) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668.
33. Chen, S.-H.; Huang, S.; Gao, Q.; Golik, J.; Farina, V. J. Org. Chem. 1994, 59, 1475-1484.
34. (a) 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.
35. (b) Holton, R. A.; Kim, H.-B.; Somoza, C.; 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, 1599-1600.
36. (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859.
37. Min, Z. D.; Jiang, H.; Liang, J. Y. Acta Pharm. Sin (Yaoxue Xuebao) 1989, 24, 673-677.
38. Shen, Y.-C.; Tai, H.-R.; Hsieh, P.-W.; Chen, C.-Y. Chin. Pharm. J. 1996, 48, 207-217.
39. Klein, L. L.; Li, L.; Maring, C. J.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J. J. Med. Chem. 1995, 38, 1482-1492.
40. Klein, L. L. Tetrahedron Lett. 1993, 34, 2047-2050.
41. Chaudhary, A. G.; Gharpure, M. M.; Rimoldi, J. M.; Chordia, M. D.; Gunatilaka, A. A. L.; Kingston, D. G. I.; Grover, S.; Lin, C. M.; Hamel, E. J. Am. Chem. Soc. 1994, 116, 4097-4098.
42. Kingston, D. G. I.; Chaudhary, A. G.; Chordia, M. D.; Gharpure, M.; Gunatilaka, A. A. L.; Higgs, P. I.; Rimoldi, J. M.; Sanala, L.; Jagtap, P. G.; Giannakakou, P.; Jiang, Y. Q.; Lin, C. M.; Hamel, E.; Long, B. H.; Fairchild, C. R.; Johnston, K. A. J. Med. Chem. 1998, 41, 3715-3726.
43. Chen, S.; Farina, V.; Wei, J.; Long, B.; Fairchild, C.; Mamber, S. W.; Kadow, J. F.; Vyas, D.; Doyle, T. W. Bioorg. Med. Chem. Lett. 1994, 4, 479-482.
44. (a) Samaranayake, G.; Neidigh, K. A.; Kingston, D. G. I. J. Nat. Prod. 1993, 56, 884-898.
45. (b) Datta, A.; Jayasinghe, L. R.; Georg, G. I. J. Org. Chem. 1994, 59, 4689-4690.
46. (a) Holton, R. A.; Biediger, R. J.; Boatman, P. D. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 97-121.
47. (b) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
48. (c) Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. Bioorg. Med. Chem. Lett. 1993, 3, 2467-2470.
49. (a) Mellado, W.; Magri, N. F.; Kingston, D. G. I.; Garcia-Arenas, R.; Orr, G. A.; Horwitz, S. B. Biochem. Biophys. Res. Commun. 1984, 124, 329-335.
50. (b) Chen, S.-H.; Farina, V. In The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 22, pp 165-253.
51. Williams, R. C., Jr.; Lee, J. C. Methods Enzymol. 1982, 85 Pt. D, 376-385.
52. Swindell, C. S.; Krauss, N. E.; Horwitz, S. B.; Ringel, I. J. Med. Chem. 1991, 34, 1176-1184.