Synthetic methodologies for C-nucleosides

被引:143
作者
Wu, QP [1 ]
Simons, C
机构
[1] Beijing Inst Technol, Sch Life Sci & Technol, Beijing 100081, Peoples R China
[2] Cardiff Univ, Welsh Sch Pharm, Cardiff CF10 3XF, S Glam, Wales
来源
SYNTHESIS-STUTTGART | 2004年 / 10期
关键词
C-nucleosides; organometallic reagents; Heck-type reaction; anticancer; antiviral;
D O I
10.1055/s-2004-829106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The study and synthesis of C-nucleosides has been extensive owing to their biological activity and potential as drug candidates for antiviral and anticancer therapy. Numerous synthetic strategies have also been investigated in order to optimize yields and stereoselectivity in the glycosylation reaction. Here we review one class of synthetic methods, direct condensation of a pre-formed aglycon unit with an appropriate sugar component.
引用
收藏
页码:1533 / 1553
页数:21
相关论文
共 107 条
[1]  
ALDERWEIRELDT F, 1988, NUCLEOS NUCLEOT, V7, P891
[2]   SYNTHESIS AND BIOLOGICAL EVALUATION OF 2-CARBAMOYL-5-D-RIBOFURANOSYLPYRIDINE [J].
ALDERWEIRELDT, FC ;
VRIJENS, I ;
ESMANS, EL ;
WOTRING, LL ;
TOWNSEND, LB ;
BALZARINI, J ;
DECLERCQ, E .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :891-894
[3]  
[Anonymous], BIOORGANIC CHEM NUCL
[4]   REGIOSPECIFIC REACTION OF ENOL ETHERS WITH AN ORGANOPALLADIUM SALT - STEREOCHEMICAL AND CONFORMATIONAL EFFECTS ON PRODUCT FORMATION [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :287-288
[5]   SYNTHESIS OF 5-SUBSTITUTED PYRIMIDINES .2. [J].
ASBUN, W ;
BINKLEY, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :140-&
[6]   TANDEM NUCLEOPHILIC AND RADICAL CHEMISTRY IN THE REPLACEMENT OF THE HYDROXYL GROUP BY A CARBON CARBON BOND - A CONCISE SYNTHESIS OF SHOWDOMYCIN [J].
BARTON, DHR ;
RAMESH, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :891-892
[7]   SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED PYRIDINE-C-NUCLEOSIDES .5. 3-CHLORO-4-(D-RIBOFURANOSYL)PYRIDINE AND 3-(D-RIBOFURANOSYL)-2-PYRIDONE [J].
BELMANS, M ;
VRIJENS, I ;
ESMANS, EL ;
DOMMISSE, RA ;
LEPOIVRE, JA ;
ALDERWEIRELDT, FC ;
TOWNSEND, LB ;
WOTRING, LL ;
BALZARINI, J ;
DECLERCQ, E .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (03) :307-315
[8]   SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED-2-PYRIDINE-C-NUCLEOSIDES .2. [J].
BELMANS, M ;
VRIJENS, I ;
ESMANS, E ;
DOMMISSE, R ;
LEPOIVRE, J ;
ALDERWEIRELDT, F ;
TOWNSEND, L ;
WOTRING, L ;
BALZARINI, J ;
DECLERCQ, E .
NUCLEOSIDES & NUCLEOTIDES, 1986, 5 (04) :441-455
[9]   SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED 2-PYRIDINE C-NUCLEOSIDES .1. COUPLING REACTION OF ORGANO-METALLIC PYRIDINE COMPOUNDS WITH 2,4-3,5-DI-O-BENZYLIDENE-ALDEHYDO-D-RIBOSE [J].
BELMANS, M ;
ESMANS, E ;
DOMMISSE, R ;
LEPOIVRE, J ;
ALDERWEIRELDT, F ;
BALZARINI, J ;
DECLERCQ, E .
NUCLEOSIDES & NUCLEOTIDES, 1985, 4 (04) :523-538
[10]   Polycyclic aromatic DNA-Base surrogates: High-affinity binding to an adenine-specific base-flipping DNA methyltransferase [J].
Beuck, C ;
Singh, I ;
Bhattacharya, A ;
Heckler, W ;
Parmar, VS ;
Seitz, O ;
Weinhold, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3958-3960