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Volumn 55, Issue 32, 1999, Pages 9707-9716

Synthesis and biological activity of a novel C4-C6 bridged paclitaxel analog

Author keywords

Biologically active compounds; Lactonization; Macrocycles; Taxoids

Indexed keywords

PACLITAXEL; PACLITAXEL DERIVATIVE;

EID: 0033529688     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00552-9     Document Type: Article
Times cited : (8)

References (27)
  • 1
    • 0009612103 scopus 로고    scopus 로고
    • Present address: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556.
    • Present address: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556.
  • 2
    • 0031040149 scopus 로고    scopus 로고
    • 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.
    • (1997) Annu. Rev. Med. , vol.48 , pp. 353-374
    • Rowinsky, E.K.1
  • 3
    • 0026344562 scopus 로고
    • For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34.
    • (1991) Pharmac. Ther. , vol.52 , pp. 1-34
    • Kingston, D.G.I.1
  • 5
    • 0001843250 scopus 로고
    • Paclitaxel structure-activity relationships and core skeletal rearrangements
    • Georg, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC
    • 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.
    • (1994) Taxane Anticancer Agents: Basic Science and Current Status , pp. 247-261
    • Chen, S.-H.1    Farina, V.2
  • 7
    • 0000655508 scopus 로고
    • Recent advances in the chemistry and structure-activity relationships of paclitaxel
    • George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC
    • 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.
    • (1994) Taxane Anticancer Agents: Basic Science and Current Status , pp. 203-216
    • Kingston, D.G.I.1
  • 9
    • 0029448626 scopus 로고
    • Ellis, G. P.; Luscombe, D. K., Ed.; Eisevier Science B. V.: Amsterdam
    • Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Eisevier Science B. V.: Amsterdam, 1995; Vol. 32; pp 289-337.
    • (1995) Progress in Medicinal Chemistry , vol.32 , pp. 289-337
    • Vyas, D.M.1    Kadow, J.F.2
  • 26
    • 0009568029 scopus 로고    scopus 로고
    • note
    • Various hypothetical bridged analogs were examined by changing the linker between C-4 and C-6 as well as the C-4 acyl moiety, the minimized energy was compared to determine the relative stability of the analogs. During the modeling studies, it was found that certain chains such as unsaturated di-acids or phenylene dialkyl di-acids at the C-4 position might be better than the glutaric acid in both terms of entropy (less degree of freedom) and product stability (less trans-annular interactions). Because of the unavailability of the appropriate reagents and the problems encountered in the C-4 acylation using the synthetic reagents, it was decided to simplify the question by choosing glutaric acid as the acyl source at C-4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.