SYNTHESIS OF PEPTIDE DERIVATIVES OF 5-FLUOROURACIL

被引:26
作者
NICHIFOR, M [1 ]
SCHACHT, EH [1 ]
机构
[1] STATE UNIV GHENT,DEPT ORGAN CHEM,BIOMAT RES GRP,KRIJGSLAAN 281 S-4,B-9000 GHENT,BELGIUM
关键词
D O I
10.1016/S0040-4020(01)90395-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of di-, tetra- and pentapeptides carrying 5-fluorouracil as an a-substituent of a terminal glycine moiety is described. The dipeptide compounds were synthetized by addition of ethyl glyoxylate to N-(benzyl-oxycarbonyl)-amino acid amides, subsequent acetylation of resulting hydroxyl groups,displacement of acetate groups by 5-fluorouracil, and removal of protective group. Tetra- and pentapeptides were prepared from these dipeptides by coupling methods commonly used in peptide chemistry.
引用
收藏
页码:3747 / 3760
页数:14
相关论文
共 19 条
[1]  
[Anonymous], 1984, PRACTICE PEPTIDE SYN
[2]   THE KINETICS OF THE DECOMPOSITION OF THE ADDITION COMPOUNDS FORMED BY SODIUM BISULPHITE AND A SERIES OF ALDEHYDES AND KETONES .1. [J].
BLACKADDER, DA ;
HINSHELWOOD, C .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (AUG) :2720-2727
[3]   PRODRUGS OF PEPTIDES .11. CHEMICAL AND ENZYMATIC-HYDROLYSIS KINETICS OF N-ACYLOXYMETHYL DERIVATIVES OF A PEPTIDE-LIKE BOND [J].
BUNDGAARD, H ;
RASMUSSEN, GJ .
PHARMACEUTICAL RESEARCH, 1991, 8 (10) :1238-1242
[4]  
BUNDGAARD H, 1992, J CONTROL RELEASE, V221, P63
[5]   PRODRUGS OF 5-FLUOROURACIL .1. HYDROLYSIS KINETICS AND PHYSICOCHEMICAL PROPERTIES OF VARIOUS N-ACYL DERIVATIVES OF 5-FLUOROURACIL [J].
BUUR, A ;
BUNDGAARD, H .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1984, 21 (03) :349-364
[6]   PROTEASE-ACTIVATED PRODRUGS FOR CANCER-CHEMOTHERAPY [J].
CARL, PL ;
CHAKRAVARTY, PK ;
KATZENELLENBOGEN, JA ;
WEBER, MJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (04) :2224-2228
[7]   PLASMIN-ACTIVATED PRODRUGS FOR CANCER-CHEMOTHERAPY .1. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PEPTIDYLACIVICIN AND PEPTIDYLPHENYLENEDIAMINE MUSTARD [J].
CHAKRAVARTY, PK ;
CARL, PL ;
WEBER, MJ ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (05) :633-638
[8]   PLASMIN-ACTIVATED PRODRUGS FOR CANCER-CHEMOTHERAPY .2. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF PEPTIDYL DERIVATIVES OF DOXORUBICIN [J].
CHAKRAVARTY, PK ;
CARL, PL ;
WEBER, MJ ;
KATZENELLENBOGEN, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (05) :638-644
[9]   SELECTIVE RAPID TRANSFER-HYDROGENATION OF AROMATIC NITRO-COMPOUNDS [J].
ENTWISTLE, ID ;
JOHNSTONE, RAW ;
POVALL, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1300-1301
[10]   RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE [J].
FELIX, AM ;
HEIMER, EP ;
LAMBROS, TJ ;
TZOUGRAKI, C ;
MEIENHOFER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4194-4196