Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates

Journal of Organic Chemistry

Volumn 60, Issue 2, 1995, Pages 331-336

  Greenwald, Richard B ^a   Pendri, Annapurna ^a   Bolikal, Durgadas ^a  

^a Enzon Incorporated   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SOLUBILITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0028806691     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00107a010     Document Type: Article

References (25)

1. Commercon, A.; Bizard, D.; Bernard, F; Baurzat, J. D. Tetrahedron Lett. 1992, 33, 5785-5788 and references cited.
2. Mellado, W.; Magri, N. F.; Kingston, D. G. I.; Garcia-Arenas, R. Orr, G. A.; Horwitz, S. B. Biochem. Biophys. Res. Commun. 1984, 329-336.
3. Horowitz, S. B.; Lothstein, L.; Manfredi, J. J.; Mellado, W.; Pamess, J., Roy, S. N.; Schiff, P. B.; Sorbara, L.; Zeheb, K. Ann. N. Y. Acad. Sci. 1986, 466, 733-744.
4. Magri, N. F.; Kingston, D. G. I. J. Nat. Prod. 1988, 51, 298-306.
5. Harris, J. M. Poly (Ethylene Glycol) Chemistry, Harris, J. M., Ed.; Plenum Press: New York, 1992; Chapter 1.
6. Delgado, C.; Francis, G. E.; Fisher, D. Crit. Rev. Ther. Drug Carrier Syst. 1992, 9, 249-304.
7. Harris, J. M. Macromol. J. Sci. Rev. Polymer Phys. Chem. 1985, C25, 325-373.
8. Nucci, M. L.; Shorr, R.; Abuchowski, A. Adv. Drug Deliv. Rev. 1991, 6, 133-151.
9. Mathew, A. E.; Mejillano, M. R.; Nath, J. P.; Himes, R. H.; Stella, V. J. J. Med. Chem. 1992, 35, 145-151.
10. Vyas, D. M.; Wong, H.; Crosswell, A. R.; Casazza, A. M.; Kenipe, J. O.; Mamber, S. W.; Doyle, T. W. Bioorg. Med. Chem. Lett. 1993, 3, 1357-1360.
11. Deutsch, H. M.; Glinski, J. A.; Hernandez, M.; Haugwitz, R. D.; Narayanan, V. L.; Suffness, M.; Zalkow, L. H. J. Med. Chem. 1989, 32, 788-792.
12. Abbate, F. W.; Ulrich, H. J. Appl. Polymer Sci. 1969, 13, 1929-1936.
13. Chen, S.; Huang, S.; Wei, J.; Farina, V. Tetrahedron 1993, 49, 2805-2828.
14. Samaranayake, G.; Magri, N. F.; Jitrangeri, C.; Kingston, D. G. I. J. Org. Chem. 1991, 56, 5114-5119.
15. Kingston, D. G. I.; Samaranayake, G.; Ivey, C. A. J. Nat. Prod. 1990, 53, 1-12.
16. Samaranayake, G., Ph. D. Dissertation, Virginia Polytechnic Institute & State University, 1990.
17. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons: New York, 1991; p 95.
18. Fieser, L. F.; Fieser, M. Advanced Organic Chemistry, Reinhold Publishing Corp.: New York, 1961; p 360.
19. Swindell, C. S.; Krauss, N. E., Horwitz, S. B.; Ringel, I. J. Med. Chem. 1991, 34, 1176-1184.
20. Guenard, D.; Gueritte-Voegelein, F.; Poiter, P. Acc. Chem. Res. 1993, 26, 160-167.
21. Yalkowsky, S. H.; Baneηee, S. Aqueous Solubility-Methods of Estimation for Organic Compounds; Marcel Dekker, Inc.: New York, 1992; Chapter 3.
22. Swann, R. L.; Laskowski McCall, P. J.; Vander Kuy, K.; Disburger, H. J. Residue Rev. 1983, 85, 17-28.
23. Falzone, C. J.; Benesit, A. J.; Lecomte, A. J. Tetrahedron Lett. 1992, 33, 1169-1172.
24. Huang, C. H. O.; Kingston, D. G. I.; Magri, N. F.; Samaranayake, G. J. Nat. Prod. 1986, 49, 665-669.
25. Buckmann, A. F.; Morr, M.; Kula, M. R. Biotechnol. App. Biochem. 1987, 9, 258-268.