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.

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页码：1607 / 1611

页数：5

相关论文

共 10 条

[1] STRATEGIES IN THE DESIGN OF SOLUTION-STABLE, WATER-SOLUBLE PRODRUGS .1. A PHYSICAL ORGANIC APPROACH TO PRO-MOIETY SELECTION FOR 21-ESTERS OF CORTICOSTEROIDS [J].

ANDERSON, BD ;

CONRADI, RA ;

KNUTH, KE .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1985, 74 (04) :365-374

[2] SYNTHESIS OF CONGENERS AND PRODRUGS .3. WATER-SOLUBLE PRODRUGS OF TAXOL WITH POTENT ANTITUMOR-ACTIVITY [J].

DEUTSCH, HM ;

GLINSKI, JA ;

HERNANDEZ, M ;

HAUGWITZ, RD ;

NARAYANAN, VL ;

SUFFNESS, M ;

ZALKOW, LH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :788-792

[3]

FUJITA T, 1985, J AM CHEM SOC, V74, P365

[4] MODIFIED TAXOLS .4. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF TAXOLS MODIFIED IN THE SIDE-CHAIN [J].

MAGRI, NF ;

KINGSTON, DGI .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (02) :298-306

[5]

MAGRI NF, 1985, THESIS STATE U BLACK

[6]

MCGUIRE WP, 1989, ANN INTERN MED, V111, P272

[7] PREPARATION AND BIOLOGICAL-ACTIVITY OF TAXOL ACETATES [J].

MELLADO, W ;

MAGRI, NF ;

KINGSTON, DGI ;

GARCIAARENAS, R ;

ORR, GA ;

HORWITZ, SB .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 124 (02) :329-336

[8] TAXOL - A NOVEL INVESTIGATIONAL ANTIMICROTUBULE AGENT [J].

ROWINSKY, EK ;

CAZENAVE, LA ;

DONEHOWER, RC .

JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (15) :1247-1259

[9]

STELLA VJ, Patent No. 4960790

[10] PLANT ANTITUMOR AGENTS .6. ISOLATION AND STRUCTURE OF TAXOL, A NOVEL ANTILEUKEMIC AND ANTITUMOR AGENT FROM TAXUS-BREVIFOLIA [J].

WANI, MC ;

TAYLOR, HL ;

WALL, ME ;

COGGON, P ;

MCPHAIL, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (09) :2325-&