Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogues

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2694-2703

  Gunatilaka, A A Leslie ^a,c   Ramdayal, Frank D ^a   Sarragiotto, Maria H ^a,d   Kingston, David G I ^a   Sackett, Dan L ^b   Hamel, Ernest ^b  

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

^b NATIONAL CANCER INSTITUTE   (United States)

^c UNIVERSITY OF ARIZONA   (United States)

^d STATE UNIVERSITY OF MARINGÁ   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

4 DEACETYL 4 METHOXYCARBONYL 5,20 DEOXY 5,20 SULFINYLPACLITAXEL; 4 DEACETYL 4 METHOXYCARBONYL PACLITAXEL; DOCETAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

EID: 0033574481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982095h     Document Type: Article

References (35)

1. (a) Holmes, F. A.; Kudelka, A. P.; Karanagh, 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.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp 31-57.
2. (b) Arbuck, S. G.; Blaylock, B. A. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press Inc.: Boca Raton, FL, 1995; pp 379-415.
3. (c) McGuire, W. P., Rowinsky, E. K., Eds. Paclitaxel in Cancer Treatment; Marcel Dekker: New York, Basel, Hong Kong, 1995; Vol. 8, pp 1-349.
4. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
5. For recent reviews: (a) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1-188.
6. (b) Suffness, M. Annu. Rep. Med. Chem. 1993, 28, 305-314.
7. (c) Georg, G. I.; Ali, S. M.; Zymunt, J.; Jayasinghe, J. R. Expert Opin. Ther. Pat. 1994, 12, 222-227.
8. (d) Chen, S. H.; Farina, V. Paclitaxel (Taxol) Chemistry and Structure Activity Relationships. In The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; Elsevier: New York, 1995; pp 165-223.
9. (e) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227.
10. Horwitz, S. B. Trends Pharmacol. Sci. 1992, 13, 134-136.
11. (a) Vander Velde, D. G.; George, G. I.; Grunewald, G. L.; Gunn, C. W.; Mitscher, L. A. J. Am. Chem. Soc. 1993, 115, 11650-11651.
12. (b) Dubois, J.; Guenard, D.; Gueritte-Voegelein, F.; Guerida, N.; Potier, P.; Gillet, B.; Beloeil, J. C. Tetrahedron 1993, 49, 6533-6544.
13. (c) Williams, H. J.; Scott, A. I.; Dieden, R. A.; Swindell, C. S.; Chirlian, L. E.; France, M. M.; Heerding, J. M.; Kraus, N. E. Tetrahedron 1993, 49, 6545-6560.
14. (d) Paloma, L. G.; Guy, R. K.; Wrasidio, W.; Nicolaou, K. C. Chem. Biol. 1994, 1, 107-112.
15. Fenoglio, I.; Nano, G. M.; Vander Velde, D. G.; Appendino, G. Tetrahedron Lett. 1996, 37, 3202-3206.
16. Marder-Karsenti, R.; Dubois, J.; Bricard, L.; Guénard, D.; Guéritte-Voegelein, F. J. Org. Chem. 1997, 62, 6631-6637.
17. Chen, S. H.; Huang, S.; Wei, J.; Farina, V. Tetrahedron 1993, 49, 2805-2828.
18. (a) Holton, R. A.; Somoza, C.; Kim, H. B. Liang, F.; Biediger, R. J.; Boatman, 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, 1597-1599.
19. (b) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E.; J. Nature 1994, 367, 630-634.
20. (c) Masters, J. J.; Linj, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726.
21. Chordia, M. D.; Kingston, D. G. I. J. Org. Chem. 1996, 61, 799-801.
22. Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420.
23. A similar cyclization was used in Wender's synthesis of taxol: Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758.
24. (a) Holton, R. Total Synthesis of Paclitaxel from Camphor. In Taxane Anticancer Agents: Basic Science and Current Status; George, I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1995; pp 288-301.
25. (b) Margraff, R. M.; Bezard, D.; Bouzart, J. D.; Commerçon, A. Bioorg. Med. Chem. Lett. 1994, 4, 233-236.
26. Holton, R. A.; Kim, H. B.; Somoza, C.; Liang, F.; Biendiger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Yu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N. Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
27. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1204-1208.
28. Lin, C. M.; Jiang, Y. Q.; Chaudhary, A. G.; Rimoldi, J. M.; Kingston, D. G. I.; Hamel, E. Cancer Chemother. Pharmacol. 1996, 38, 136-140.
29. Giannakakou, P.; Sackett, D. L.; Kang, Y.-K; Zhan, Z.; Buters, J. T. M.; Fojo, T.; Poruchynsky, M. S. J. Biol. Chem. 1997, 272, 17118-17125.
30. Neidigh, K. A.; Gharpure, M. M.; Rimoldi, J. M.; Kingston, D. G. I.; Jiang, Y. Q.; Hamel, E. Tetrahedron Lett. 1994, 35, 6839-6842.
31. Dewar, M. J. S.; Mole, T. J. Chem. Soc. 1956, 1441-1443.
32. Browne, D. T. In Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S., Eds.; Interscience: New York, 1968.
33. Musa, A.; Sridharan, B.; Lee, H.; Mattern, D. L. J. Org. Chem. 1996, 61, 5481-5484. Kreyenschmidt, M.; Baumgarten, M.; Tyutyulkov, N.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1957-1959.
34. Musa, A.; Sridharan, B.; Lee, H.; Mattern, D. L. J. Org. Chem. 1996, 61, 5481-5484. Kreyenschmidt, M.; Baumgarten, M.; Tyutyulkov, N.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1957-1959.
35. House, H. O.; Ghali, N. I.; Haack, J. L.; VanDerveer, D. J. Org. Chem. 1980, 45, 1807-1817.