Synthesis and biological evaluation of new 4-deacety-1,7,9-trideoxy-10- oxopaclitaxel via sinenxan A

Synthetic Communications

Volumn 37, Issue 21, 2007, Pages 3779-3791

  Du, Huixia ^a   Zhang, Meng ^a   Yin, Dali ^a   Li, Yan ^a   Chen, Xiaoguang ^a  

^a PEKING UNION MEDICAL COLLEGE   (China)

Author keywords

4 deacety 1,7,9 trideoxy 10 oxopaclitaxel; Biological evaluation; Sinenxan A; Synthesis

Indexed keywords

4 DEACETY 1,7,9 TRIDEOXY 10 OXOPACLITAXEL; PACLITAXEL DERIVATIVE; SINENXAN A; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY;

EID: 35348964068     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701569767     Document Type: Article

References (10)

1. Ojima, I.; Slater, J. C.; Kuduk, S. D.; Takeuchi, C. S.; Gimi, R. H.; Sun, C-M.; Park, Y.-H.; Pera, P.; Veith, J. M.; Bernacki, R. J. Syntheses and structure-activity relationship of taxoids derived from 14β-hydroxy-10- deacetylbaccatin III. J. Med. Chem. 1997, 40, 267-278.
2. Ojima, I.; Wang, T.; Miller, M. L.; Lin, S. N.; Borella, C. P.; Geng, X. D.; Pera, P.; Bernacki, R. J. Synthesis and structure-activity relationships of new second-generation taxoids. Bioorg. Med. Chem. Lett. 1999, 9, 3423-3428.
3. Zhang, M.; Yin, D. L.; Guo, J. Y.; Liang, X. T. Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A. Tetrahedron 2005, 61, 5519-5527.
4. Wiegerinck, P. H. G.; Fluks, L.; Hammink, J. B.; Mulders, S. J. E.; de Groot, F. M. H.; van Rozendaal, H. L. M.; Scheeren, H. W. Semisynthesis of some 7-deoxypaclitaxel analogs from taxine B. J. Org. Chem. 1996, 61, 7092-7100.
5. Ettouati, L.; Ahond, A.; Poupat, C.; Potier, P. Premiere. Hémisynthèse d'un Composé de Type Taxane Porteur d'un Groupement Oxétane en 4 (20), 5. Tetrahedron 1991, 47, 9823. 6.
6. (a) Horiguchi, T.; Oritani, T.; Kiyota, H. Synthesis and antitumor activity of 2-(msubstituted-benzoyl) baccatin III analogs from taxinine. Tetrahedron 2003, 59, 1529-1538;
7. (b) Chen, S. H.; Kadow, J. F.; Farina, V.; Johnston, K.; Fairchild, C. First syntheses of novel paclitaxel (taxol) analogs modified at the C4-position. J. Org. Chem. 1994, 59, 6156-6158;
8. (c) Chen, S. H.; Fairchild, C.; Long, B. H. Synthesis and biological evaluation of novel C-4 aziridine-bearing paclitaxel. J. Med. Chem. 1995, 38, 2263-2267.
9. Kingston, D. G. I. Recent advances in the chemistry of taxol. J. Nat. Prod. 2000, 63, 726-734.
10. Denis, J. N.; Greene, A. E. A highly efficient, practical approach to natural taxol. J. Am. Chem. Soc. 1988, 110, 5917-5919.