C-2 modified taxol analogs with improved aqueous solubility

Bulletin of the Korean Chemical Society

Volumn 20, Issue 12, 1999, Pages 1389-1390

  Kim, Seok Chan ^a   Moon, Man Sik ^a   Cheong, Chan Seong ^b  

^a Kookmin University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

TAXOL; TAXOL DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; CYTOTOXICITY; DRUG FORMULATION; DRUG SOLUBILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LETTER; REACTION ANALYSIS;

EID: 0033590115     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. Paclitaxel is the generic name for Taxol, which is now a registered trademark.
2. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Cliem. Soc. 1971, 93, 2325.
3. (a) Suffness, M. Ann. Rep. Med. Cliem. 1993,28, 305.
4. (b) Adams, J. D.; Flora, K. P.; Goldspiel, B. R.; Wilson, J. W; Finley, R.; Arbuck, S. G. J. Natl. Cancer Inst. Monographs 1993,75,141.
5. (a) Rowinsky, E. K.; Cazenave, L. A.; Donehower, R. C. J. Natl. Cancer Inst. 1990,82, 1247.
6. (b) Dye, D.; Watkins, J. Br. Med. J. 1980,250,1353.
7. Weiss, R. B.; Donehower, R. C.; Wiernik, P. H.; Ohnuma, T.; Gralla, R. J.; Trump, D. L.; Baker, J. R.; Leyland-Jones, B. J. Clin. Oncol. 1990, 8, 1263.
8. (a) Samaranayake, G.; Neidigh, K. A.; Kingston, D. G. I. 7. Nat. Prod. 1993, 56, 884.
9. (b) Datta, A.; Jayasinghe, L.; Georg, G. I. J. Med. Cliem. 1994, 37, 4258.
10. Chordia, M. D.; Chaudhary, A. G.; Kingston, D. G.; Jiang, Y. Q.; Hamel, E. Tetrahedron Lett. 1994, 35, 6843.
11. Chen, S.H.; Kadow, J. F.; Farina, V.; Fairchild, C. R.; Johnston, K. A. J. Org. Client. 1994, 59, 6156.
12. (e) Kim, S. C.; Moon, M. S.; Choi, K. M.; Jun, S. J.; Kim, H. K.; Jung, D. I.; Lee, K. S.; Chai, K. B. Bull. Korean Client. Soc. 1998, 19, 1027.
13. (f) Kim, S. C.; Moon, M. S.; Choi, K. M.; Cheong, C. S.; June, D. L; Chai, K. B. Kor. J. Med. Cliem. 1998,8, 88.
14. Kim, S. C.; Chai, K. B. Kor. J. Med. Cliem. 1997, 7,1.
15. (a) Wahl, A.; Guéritte-Voegelein, F.; Guénard, Die Goff MT.; Potier, P. Tetrhedwn 1992,48,6965.
16. (b) Samaranayake, G.; Neidigh, K. A.; Kingston, D. G. I. J. Nat. Prod. 1993, 56, 884.
17. (a) Holton, R. A. Em. Pat. Appl. EP 400,971, 1990.
18. (b) Ojima, I.; Habus, L; Zaho, M; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigand, T. Tetrahedron 1992,48, 6985.
19. 3, 300 MHz) δ 1.07 (s, 3H, Me16), 1.19 (s, 3H, Me17), 1.73 (s, 3H, Me19), 1.77 (s, 3H, Me18), 1.86 (m, 1H, H6β), 2.28 (m, 2H, H14), 2.38 (s, 3H, 4Ac), 2.54 (m, 1H, H6α), 3;88 (d, 1H, J = 7.3 Hz, H3), 4.15 (d, 1H, J = 8.2 Hz, H20β),4.17(m, 1H, 2'OH),4.22 (d, 1H, J = 8.2 Hz, H20α), 4.22 (m, 1H, H7), 4.78 (d, 1H, J = 2.5 Hz, H2′), 4.90 (dd, 1H,7= 1.1, 9.3 Hz, H5), 5.17 (s, 1H, H10), 5.64 (d, 1H, J = 7.3 Hz, H2), 5.78 (dd, 1H, J = 2.3,9.3 Hz, H3′), 6.20 (t, 1H, J = 8.1 Hz, H13), 7.09 (d, 1H, J = 9.1 Hz, NH), 7.55 (m, 10H, 2′-NBz and 3′-Ph), 7.90 (d, 1H, J = 1.8 Hz, isonicotinoyl), 7.91 (d, 1H, J= 1.6 Hz, isonicotinoyl), 8.79 (d, 1H, J = 1.6 Hz, isonicotinoyl), 8.80 (d, 1H, J= 1.8 Hz, isonicotinoyl).
20. (a) Rose, W. C. Anti-Cancer Drugs 1992,3,311.
21. (b) Waugh, W.; Trissel, L.; Stella, V. Am. J. Hosp. Pharm. 1991, 48, 1520.