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Volumn 55, Issue 21, 1999, Pages 6567-6576

Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers

Author keywords

Antitumour compounds; Dimers; Taxoids

Indexed keywords

10 DEACETYLBACCATIN; 2' DEACETOXYAUSTROSPICATINE; DIMER; DOCETAXEL; PACLITAXEL; TAXANE DERIVATIVE; TAXOID; UNCLASSIFIED DRUG;

EID: 0033591156     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00290-2     Document Type: Article
Times cited : (10)

References (41)
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    • Part XXXII
    • Part XXXIII in the Series "The Chemistry and Occurrence of Taxane Derivatives". Part XXXII: Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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    • b) Robert, J. Drugs Fut. 1997, 22, 149-158.
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    • 0031581815 scopus 로고    scopus 로고
    • Non-P-gl-mediated mechanisms of resistance to paclitaxel are also known
    • Wills, P.; Phung-Ba, V.; Warnery, A.; Lechardeur, D.; Raissi, S.; Hidalgo, I.J.; Schermann, D. Biochem.pharm. 1994, 48, 1528-1530. Non-P-gl-mediated mechanisms of resistance to paclitaxel are also known: Parekc, H.; Wiesen K.; Simpkins, H. Biochem. Pharmacol. 1997, 53, 461-470.
    • (1997) Biochem. Pharmacol. , vol.53 , pp. 461-470
    • Parekc, H.1    Wiesen, K.2    Simpkins, H.3
  • 21
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    • Paclitaxel itself could not be directly employed for the synthesis of 3a, since its 2'-protected- and 2',7-diprotected (TES, Cbz) derivatives could not be selectively deacetylated at C-10
    • Paclitaxel itself could not be directly employed for the synthesis of 3a, since its 2'-protected- and 2',7-diprotected (TES, Cbz) derivatives could not be selectively deacetylated at C-10.
  • 22
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    • The diol 9c was unreactive toward succinic anhydride. No reaction took also place when 7,10-diTES-10-deacetylbaccatin III was treated with this reagent
    • The diol 9c was unreactive toward succinic anhydride. No reaction took also place when 7,10-diTES-10-deacetylbaccatin III was treated with this reagent.
  • 26
    • 0013533809 scopus 로고    scopus 로고
    • 15a but can be efficiently carried out in DMF with only 1.1 equivalents of TES-C1 and imidazole
    • 15a but can be efficiently carried out in DMF with only 1.1 equivalents of TES-C1 and imidazole.
  • 37
    • 0013521948 scopus 로고    scopus 로고
    • Only the less hindered 7-TES group could be selectively removed with 1 mol. equiv. TBAF
    • Only the less hindered 7-TES group could be selectively removed with 1 mol. equiv. TBAF.
  • 39
    • 0025871603 scopus 로고
    • Discrepancies of this type were first reported for a 11(15→1)abeo analogue of paclitaxel (Samaranayake, G.; Magri, N.F.; Jitrangsri, C.; Kingston, D.G.I. J. Org. Chem. 1991, 56, 5114-5119). Synthetic paclitaxelanalogues which improved tubulin affinity but a remarkably reduced cytotoxicity have been recently reported (Kalr, U.; Graf, H.; Schenk., O.; Röhr, B.; Schulz, H. Bioorg. Med. Chem. Lett. 1998, 8, 1397-1402).
    • (1991) J. Org. Chem. , vol.56 , pp. 5114-5119
    • Samaranayake, G.1    Magri, N.F.2    Jitrangsri, C.3    Kingston, D.G.I.4
  • 40
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    • Discrepancies of this type were first reported for a 11(15→1)abeo analogue of paclitaxel (Samaranayake,G.; Magri, N.F.; Jitrangsri, C.; Kingston, D.G.I. J. Org. Chem. 1991, 56, 5114-5119). Synthetic paclitaxel analogues which improved tubulin affinity but a remarkably reduced cytotoxicity have been recently reported (Kalr, U.; Graf, H.; Schenk., O.; Röhr, B.; Schulz, H. Bioorg. Med. Chem. Lett. 1998, 8, 1397-1402).
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1397-1402
    • Kalr, U.1    Graf, H.2    Schenk, O.3    Röhr, B.4    Schulz, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.