Conformationally restricted paclitaxel analogues: Macrocyclic mimics of the "hydrophobic collapse" conformation

被引：40
作者：
Boge, TC
Wu, ZJ
Himes, RH
Vander Velde, DG
Georg, GI
机构：
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
[2] Univ Kansas, Dept Mol Biosci, Lawrence, KS 66045 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 20期
关键词：
D O I：
10.1016/S0960-894X(99)00522-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Conformationally restricted macrocyclic analogues of paclitaxel were prepared, by connecting the 3'-phenyl group and the 2-benzoate moiety with two-atom tethers to mimic the "hydrophobic collapse" paclitaxel conformation. The analogues did not show activity in a tubulin assembly assay. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：3047 / 3052
页数：6
相关论文
共 15 条
  • [1] THE EFFECT OF THE AROMATIC RINGS OF TAXOL ON BIOLOGICAL-ACTIVITY AND SOLUTION CONFORMATION - SYNTHESIS AND EVALUATION OF SATURATED TAXOL AND TAXOTERE ANALOGS
    BOGE, TC
    HIMES, RH
    VANDERVELDE, DG
    GEORG, GI
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) : 3337 - 3343
  • [2] SYNTHESIS AND BIOLOGY OF SUBSTITUTED 3'-PHENYL TAXOL ANALOGS
    GEORG, GI
    CHERUVALLATH, ZS
    HARRIMAN, GCB
    HEPPERLE, M
    PARK, H
    HIMES, RH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (19) : 2331 - 2336
  • [3] SYNTHESIS OF BIOLOGICALLY-ACTIVE 2-BENZOYL PACLITAXEL ANALOGS
    GEORG, GI
    ALI, SM
    BOGE, TC
    DATTA, A
    FALBORG, L
    PARK, H
    MEJILLANO, M
    HIMES, RH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (03) : 259 - 264
  • [4] Synthesis, conformational analysis, and biological evaluation of heteroaromatic taxanes
    Georg, GI
    Harriman, GCB
    Hepperle, M
    Clowers, JS
    VanderVelde, DG
    Himes, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) : 2664 - 2676
  • [5] AN EFFICIENT SEMISYNTHESIS OF TAXOL FROM (3R,4S)-N-BENZOYL-3-[(T-BUTYLDIMETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE AND 7-(TRIETHYLSILYL)BACCATIN III
    GEORG, GI
    CHERUVALLATH, ZS
    HARRIMAN, GCB
    HEPPERLE, M
    PARK, H
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2467 - 2470
  • [6] GEORG GI, 1995, TAXOL SCI APPL, P317
  • [7] Gomez Paloma L, 1994, Chem Biol, V1, P107
  • [8] PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES
    HART, DJ
    KANAI, K
    THOMAS, DG
    YANG, TK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) : 289 - 294
  • [9] HOLMES FA, 1995, ACS SYM SER, V583, P31
  • [10] CRYSTAL AND MOLECULAR-STRUCTURE OF PACLITAXEL (TAXOL)
    MASTROPAOLO, D
    CAMERMAN, A
    LUO, YG
    BRAYER, GD
    CAMERMAN, N
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (15) : 6920 - 6924
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