TOPLISS APPROACH TO THE SYNTHESIS OF BIOLOGICALLY-ACTIVE SUBSTITUTED N-BENZOYL TAXOL ANALOGS

被引:16
作者
GEORG, GI [1 ]
BOGE, TC [1 ]
CHERUVALLATH, ZS [1 ]
HARRIMAN, GCB [1 ]
HEPPERLE, M [1 ]
PARK, H [1 ]
HIMES, RH [1 ]
机构
[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045
关键词
D O I
10.1016/S0960-894X(01)80378-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of compounds, directed by the Topliss Operational Scheme, were synthesized and evaluated to investigate structure activity relationships of the N-benzoyl moiety of taxol. Evaluation of the newly prepared derivatives in the microtubule assembly assay and for cytotoxicity revealed that they possessed biological properties similar to taxol.
引用
收藏
页码:1825 / 1830
页数:6
相关论文
共 45 条
  • [31] ANTI-LEUKEMIC ALKALOIDS FROM TAXUS-WALLICHIANA ZUCC
    MILLER, RW
    POWELL, RG
    SMITH, CR
    ARNOLD, E
    CLARDY, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) : 1469 - 1474
  • [32] CHEMISTRY AND BIOLOGY OF TAXOL
    NICOLAOU, KC
    DAI, WM
    GUY, RK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (01) : 15 - 44
  • [33] EFFICIENT AND PRACTICAL ASYMMETRIC-SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN, N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE, AND ITS ANALOGS VIA CHIRAL 3-HYDROXY-4-ARYL-BETA-LACTAMS THROUGH CHIRAL ESTER ENOLATE-IMINE CYCLOCONDENSATION
    OJIMA, I
    HABUS, I
    ZHAO, MZ
    GEORG, GI
    JAYASINGHE, LR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1681 - 1683
  • [34] NEW AND EFFICIENT APPROACHES TO THE SEMISYNTHESIS OF TAXOL AND ITS C-13 SIDE-CHAIN ANALOGS BY MEANS OF BETA-LACTAM SYNTHON METHOD
    OJIMA, I
    HABUS, I
    ZHAO, M
    ZUCCO, M
    PARK, YH
    SUN, CM
    BRIGAUD, T
    [J]. TETRAHEDRON, 1992, 48 (34) : 6985 - 7012
  • [35] ASYMMETRIC-SYNTHESIS OF ALPHA-KETO BETA-LACTAMS VIA [2+2] CYCLOADDITION REACTION - A CONCISE APPROACH TO OPTICALLY-ACTIVE ALPHA-HYDROXY BETA-LACTAMS AND BETA-ALKYL(ARYL)ISOSERINES
    PALOMO, C
    AIZPURUA, JM
    MIRANDA, JI
    MIELGO, A
    ODRIOZOLA, JM
    [J]. TETRAHEDRON LETTERS, 1993, 34 (39) : 6325 - 6328
  • [36] THE TAXOIDS - PACLITAXEL (TAXOL(R)) AND DOCETAXEL (TAXOTERE(R))
    PAZDUR, R
    KUDELKA, AP
    KAVANAGH, JJ
    COHEN, PR
    RABER, MN
    [J]. CANCER TREATMENT REVIEWS, 1993, 19 (04) : 351 - 386
  • [37] THE CLINICAL-PHARMACOLOGY AND USE OF ANTIMICROTUBULE AGENTS IN CANCER CHEMOTHERAPEUTICS
    ROWINSKY, EK
    DONEHOWER, RC
    [J]. PHARMACOLOGY & THERAPEUTICS, 1991, 52 (01) : 35 - 84
  • [38] STEARNS ME, 1992, CANCER RES, V52, P3776
  • [39] Suffnees M., 1985, ALKALOIDS, V25, P3
  • [40] SUFFNESS M, 1993, ANNU REP MED CHEM, V28, P305