MODIFIED TAXOLS .6. PREPARATION OF WATER-SOLUBLE PRODRUGS OF TAXOL

被引:68
|
作者
ZHAO, ZY
KINGSTON, DGI
CROSSWELL, AR
机构
[1] VIRGINIA POLYTECH INST & STATE UNIV,DEPT CHEM,BLACKSBURG,VA 24061
[2] BRISTOL MYERS SQUIBB,WALLINGFORD,CT 06492
来源
JOURNAL OF NATURAL PRODUCTS | 1991年 / 54卷 / 06期
关键词
D O I
10.1021/np50078a018
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Three H2O-soluble prodrugs of taxol have been prepared using a sulfonate group as the H2O-solubilizing group. The first two contain taurine or 3-amino-1-sulfopropionic acid linked to the 2'-position of taxol through a succinate group, and a novel method of preparing these derivatives is described. The third derivative is prepared by the Michael addition of bisulfite to 2'-acryloyltaxol. A 2'-(gamma-aminobutyryl)taxol salt was too unstable to be isolable.
引用
收藏
页码:1607 / 1611
页数:5
相关论文
共 50 条
  • [1] Recent studies on taxol related water-soluble prodrugs
    Li, JL
    Feng, X
    Liu, B
    Yuan, YJ
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2001, 21 (06) : 428 - 435
  • [2] PHOSPHATASE ACTIVATED WATER-SOLUBLE PRODRUGS OF TAXOL(R)
    VYAS, DM
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 142 - MEDI
  • [3] HIGHLY WATER-SOLUBLE TAXOL DERIVATIVES - 2'-POLYETHYLENEGLYCOL ESTERS AS POTENTIAL PRODRUGS
    GREENWALD, RB
    PENDRI, A
    BOLIKAL, D
    GILBERT, CW
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (20) : 2465 - 2470
  • [4] SYNTHESIS OF CONGENERS AND PRODRUGS .3. WATER-SOLUBLE PRODRUGS OF TAXOL WITH POTENT ANTITUMOR-ACTIVITY
    DEUTSCH, HM
    GLINSKI, JA
    HERNANDEZ, M
    HAUGWITZ, RD
    NARAYANAN, VL
    SUFFNESS, M
    ZALKOW, LH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) : 788 - 792
  • [5] SYNTHESIS AND EVALUATION OF SOME WATER-SOLUBLE PRODRUGS AND DERIVATIVES OF TAXOL WITH ANTITUMOR-ACTIVITY
    MATHEW, AE
    MEJILLANO, MR
    NATH, JP
    HIMES, RH
    STELLA, VJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) : 145 - 151
  • [6] ELECTRON EXCHANGE POLYMERS .6. PREPARATION OF WATER-SOLUBLE AND WATER-SWELLABLE POLYMERS
    EZRIN, M
    CASSIDY, HG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (11) : 2525 - 2526
  • [7] PROPERTIES OF CYCLODEXTRINS .6. WATER-SOLUBLE CYCLODEXTRIN-DERIVATIVES - PREPARATION AND ANALYSIS
    LAMMERS, JNJ
    KOOLE, JL
    HURKMANS, J
    [J]. STARKE, 1971, 23 (05): : 167 - &
  • [8] Synthesis of water-soluble phenytoin prodrugs
    Bosch, J
    Roca, T
    Domènech, J
    Suriol, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) : 1859 - 1862
  • [9] NOVEL WATER-SOLUBLE PHOSPHATE PRODRUGS OF TAXOL(R) POSSESSING IN-VIVO ANTITUMOR-ACTIVITY
    UEDA, Y
    MIKKILINENI, AB
    KNIPE, JO
    ROSE, WC
    CASAZZA, AM
    VYAS, DM
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (08) : 1761 - 1766
  • [10] MODIFIED TAXOLS .5. REACTION OF TAXOL WITH ELECTROPHILIC REAGENTS AND PREPARATION OF A REARRANGED TAXOL DERIVATIVE WITH TUBULIN ASSEMBLY ACTIVITY
    SAMARANAYAKE, G
    MAGRI, NF
    JITRANGSRI, C
    KINGSTON, DGI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17): : 5114 - 5119