SCHOTTEN-BAUMANN ACYLATION OF N-DEBENZOYLTAXOL - AN EFFICIENT ROUTE TO N-ACYL TAXOL ANALOGS AND THEIR BIOLOGICAL EVALUATION

被引:51
作者
GEORG, GI [1 ]
BOGE, TC [1 ]
CHERUVALLATH, ZS [1 ]
HARRIMAN, GCB [1 ]
HEPPERLE, M [1 ]
PARK, H [1 ]
机构
[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045
关键词
D O I
10.1016/S0960-894X(01)80139-6
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient route to N-acyl taxol analogues is described utilizing N-debenzoyltarol (II). Acylation of 11 with various acid chlorides under Schotten-Baumann conditions led to a facile one step synthesis of several N-acyl taxol analogues from a common intermediate.
引用
收藏
页码:335 / 338
页数:4
相关论文
共 12 条
[1]   SYNTHESIS OF BIOLOGICALLY-ACTIVE TAXOL ANALOGS WITH MODIFIED PHENYLISOSERINE SIDE-CHAINS [J].
GEORG, GI ;
CHERUVALLATH, ZS ;
HIMES, RH ;
MEJILLANO, MR ;
BURKE, CT .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (22) :4230-4237
[2]   TAXOL PHOTOAFFINITY LABEL - 7-(PARA-AZIDOBENZOYL)TAXOL SYNTHESIS AND BIOLOGICAL EVALUATION [J].
GEORG, GI ;
HARRIMAN, GCB ;
HIMES, RH ;
MEJILLANO, MR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (07) :735-738
[3]  
GEORG GI, 1994, IN PRESS MED CHEM LE
[4]  
GEORG GI, 1993, IN PRESS TAXOL SCI A
[5]  
GEORG GI, 1993, IN PRESS CURR OPIN T
[6]  
GEORGE GI, 1993, IN PRESS BIOORG MED, V3
[7]  
HORWITZ SB, 1992, TRENDS PHARMACOL SCI, V13, P134
[8]   TAXOL - AN ANTIMITOTIC AGENT WITH A NEW MECHANISM OF ACTION [J].
MANFREDI, JJ ;
HORWITZ, SB .
PHARMACOLOGY & THERAPEUTICS, 1984, 25 (01) :83-125
[9]   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 [J].
OJIMA, I ;
HABUS, I ;
ZHAO, MZ ;
GEORG, GI ;
JAYASINGHE, LR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1681-1683
[10]  
Ojima L., 1993, TETRAHEDRON LETT, V34, P4149