Synthesis and biological evaluation of C-1 and ring modified A- norpaclitaxels

Tetrahedron

Volumn 55, Issue 30, 1999, Pages 9089-9100

  Yuan, Haiqing ^a   Kingston, David G I ^a   Long, Byron H ^b   Fairchild, Craig A ^b   Johnston, Kathy A ^b  

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

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

Baeyer Villiger reactions; Ozonolysis; Rearrangements; Taxoids

Indexed keywords

1 DEISOPROPENYL 1 ACETOXY A NORPACLITAXEL; 1 DEISOPROPENYL 1 ACETOYL 8,9 OXIDO A NORPACLITAXEL; 1 DEISOPROPENYL A NORPACLITAXEL; A NOR C PACLITAXEL; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; DRUG ISOLATION; DRUG SYNTHESIS; GEOMETRY; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE IMAGING; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

EID: 0033597988     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00500-1     Document Type: Article

References (25)

1. Present address: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556
2. For a review of the development and clinical utility of the taxane class of anticancer agents, see Rowinsky, E. K. Annu. Rev. Med. 1997, 48, 353-374.
3. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
4. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
5. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
6. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
7. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
8. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
9. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
10. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227. (c) Chen, S.-H.; Farina, V. Paclitaxel structure-activity relationships and core skeletal rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D.M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 247-261. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The medicinal chemistry of taxol. In Taxol: Science and Applications; Suffness, M.; Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp. 317-375. (e) Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp. 203-216. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K.; Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp. 289-337. (h) Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
11. Samaranayake, G.; Magri, N. F.; Jitrangsri, C.; Kingston, D. G. I. J. Org. Chem. 1991, 56, 5114-5119.
12. (a) Wahl, A.; Guéritte-Voegelein, G.; Guénard, D. Tetrahedron 1992, 48, 6965-6974. (b) Chen, S. H.; Huang, S.; Wei, J.; Farina, V. J. Org. Chem. 1993, 58, 4520-4521.
13. (a) Wahl, A.; Guéritte-Voegelein, G.; Guénard, D. Tetrahedron 1992, 48, 6965-6974. (b) Chen, S. H.; Huang, S.; Wei, J.; Farina, V. J. Org. Chem. 1993, 58, 4520-4521.
14. Chordia, M. D.; Kingston, D. G. I.; Hamel, E.; Lin, C. M.; Long, B. H.; Fairchild, C. A.; Johnston, K. A.; Rose, W. C. Bioorg. Med. Chem. 1997, 5, 941-947.
15. Kingston, D. G. I.; Chaudhary, A. G.; Chordia, M. D.; Gharpure, M.; Gunatilaka, A. A. L.; Higgs, P. I.; Rimoldi, J. M.; Samala, L.; Jagtap, P. G.; Giannakakou, P.; Jiang, Y. Q.; Lin, C. M.; Hamel, E.; Long, B. H.; Fairchild, C. A.; Johnston K. A J. Med. Chem. 1998, 41, 3715-3726.
16. Chordia, M. D.; Kingston, D. G. I. Tetrahedron 1997, 53, 5699-5710.
17. Vander Velde, D. G.; Georg, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 115, 11650-11651.
18. (a) Cooper, M. S.; Heaney, H.; Newbold, A. J.; and Sanderson, W. R. Synlett 1990, 533-535. (b) Jackson, W. P. Synlett 1990, 536-536.
19. (a) Cooper, M. S.; Heaney, H.; Newbold, A. J.; and Sanderson, W. R. Synlett 1990, 533-535. (b) Jackson, W. P. Synlett 1990, 536-536.
20. Kingston, D. G. I.; Chordia, M. D.; Jagtap, P. G.; Liang, J.; Shen, Y.-C.; Long, B. H.; Fairchild, C. R.; Johnston, K. A. J. Org. Chem., 1999, 64, 1814-1822.
21. Chen, S. H.; Huang, S.; Roth, G. P. Tetrahedron Lett. 1995, 36, 8933-8936.
22. Liang, X.; Kingston, D. G. I.; Lin, C. M.; Hamel, E. Tetrahedron Lett. 1995, 36, 2901-2904.
23. Liang, X.; Kingston, D. G. I.; Long, B. H.; Fairchild, C. A.; Johnston, K. A. Tetrahedron 1997, 53, 3441-3456.
24. Chordia, M. D.; Kingston, D. G. I.; Hamel, E.; Lin, C. M.; Long, B. H.; Fairchild, C. A.; Johnston, K. A.; Rose, W. C. Bioorg. Med. Chem. 1997, 5, 941-947.
25. Rodi, D. J.; Janes, R. W.; Sanganee, H. J.; Holton, R. A.; Wallace, B. A.; Makowski, L. J. Mol. Biol. 1999, 285, 197-203.