TAXOL PHOTOAFFINITY LABEL - 7-(PARA-AZIDOBENZOYL)TAXOL SYNTHESIS AND BIOLOGICAL EVALUATION

被引:28
作者
GEORG, GI [1 ]
HARRIMAN, GCB [1 ]
HIMES, RH [1 ]
MEJILLANO, MR [1 ]
机构
[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045
关键词
TAXOL; SYNTHESIS; BETA-LACTAMS; MICROTUBULE ASSEMBLY; PHOTOAFFINITY LABEL;
D O I
10.1016/S0960-894X(00)80402-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient semi-synthetic approach utilizing the appropriately functionalized (3R,4S)-3-hydroxy-4-phenyl-2-azetidinone (4) and 7-(p-azidobenzoyl)baccatin III (3) is described which leads to the targeted biologically active taxol photoaffinity label 6
引用
收藏
页码:735 / 738
页数:4
相关论文
共 22 条
  • [1] Bayley H., 1983, PHOTOGENERATED REAGE
  • [2] SYNTHESIS OF A PHOTOREACTIVE TAXOL SIDE-CHAIN
    CHATTERJEE, A
    WILLIAMSON, JS
    ZJAWIONY, JK
    PETERSON, JR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (01) : 91 - 94
  • [3] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL
    DENIS, JN
    GREENE, AE
    GUENARD, D
    GUERITTEVOEGELEIN, F
    MANGATAL, L
    POTIER, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) : 5917 - 5919
  • [4] NOVEL BIOLOGICALLY-ACTIVE TAXOL ANALOGS - BACCATIN-III 13-(N-(PARA-CHLOROBENZOYL)-(2'R,3'S)-3'-PHENYLISOSERINATE) AND BACCATIN-III 13-(N-BENZOYL-(2'R,3'S)-3'-(PARA-CHLOROPHENYL)ISOSERINATE)
    GEORG, GI
    CHERUVALLATH, ZS
    HIMES, RH
    MEJILLANO, MR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (04) : 295 - 298
  • [5] GEORG GI, IN PRESS J MED CHEM
  • [6] RELATIONSHIPS BETWEEN THE STRUCTURE OF TAXOL ANALOGS AND THEIR ANTIMITOTIC ACTIVITY
    GUERITTEVOEGELEIN, F
    GUENARD, D
    LAVELLE, F
    LEGOFF, MT
    MANGATAL, L
    POTIER, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) : 992 - 998
  • [7] HOLTON RA, COMMUNICATION
  • [8] THE CHEMISTRY OF TAXOL, A CLINICALLY USEFUL ANTICANCER AGENT
    KINGSTON, DGI
    SAMARANAYAKE, G
    IVEY, CA
    [J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (01): : 1 - 12
  • [9] THE CHEMISTRY OF TAXOL
    KINGSTON, DGI
    [J]. PHARMACOLOGY & THERAPEUTICS, 1991, 52 (01) : 1 - 34
  • [10] MODIFIED TAXOLS .3. PREPARATION AND ACYLATION OF BACCATIN-III
    MAGRI, NF
    KINGSTON, DGI
    JITRANGSRI, C
    PICCARIELLO, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) : 3239 - 3242