Isoxazolidine analogues of pseudouridine: a new class of modified nucleosides

被引:44
作者
Chiacchio, U
Corsaro, A
Mates, J
Merino, P
Piperno, A
Rescifina, A
Romeo, G
Romeo, R
Tejero, T
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Univ Zaragoza, Fac Ciencias, Dept Quim Organ, E-50009 Zaragoza, Spain
[3] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy
关键词
glycosidic bond; pseudouridine; cycloaddition;
D O I
10.1016/S0040-4020(03)00689-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddition methodology. The obtained compounds are structurally related to natural pseudouridine, where the sugar moiety is replaced by an isoxazolidine ring. Different experimental conditions, and the effect of additives on the cycloaddition process, have been examined; the best results were obtained when the cycloaddition reaction was performed under microwave irradiation (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4733 / 4738
页数:6
相关论文
共 57 条
[1]   SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
AGROFOGLIO, L ;
SUHAS, E ;
FARESE, A ;
CONDOM, R ;
CHALLAND, SR ;
EARL, RA ;
GUEDJ, R .
TETRAHEDRON, 1994, 50 (36) :10611-10670
[2]   CRYSTAL-STRUCTURE OF UNMODIFIED TRNA(GLN) COMPLEXED WITH GLUTAMINYL-TRANSFER-RNA SYNTHETASE AND ATP SUGGESTS A POSSIBLE ROLE FOR PSEUDO-URIDINES IN STABILIZATION OF RNA STRUCTURE [J].
ARNEZ, JG ;
STEITZ, TA .
BIOCHEMISTRY, 1994, 33 (24) :7560-7567
[3]   Preparation and reactions of zincated thymine derivatives [J].
Bérillon, L ;
Wagner, R ;
Knochel, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9117-9121
[4]   MODULATION OF LEUKOCYTE GENETIC EXPRESSION BY NOVEL PURINE NUCLEOSIDE ANALOGS - A NEW APPROACH TO ANTITUMOR AND ANTIVIRAL AGENTS [J].
BONNET, PA ;
ROBINS, RK .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (06) :635-653
[5]  
CHALLAND R, 1997, ANTIVIRAL CHEMOTHERA
[6]  
Charette M, 2000, IUBMB LIFE, V49, P341
[7]  
Chaudhuri NC, 1997, SYNLETT, P341
[8]  
Chiacchio U, 2001, EUR J ORG CHEM, V2001, P1893, DOI 10.1002/1099-0690(200105)2001:10<1893::AID-EJOC1893>3.0.CO
[9]  
2-K
[10]  
Chiacchio U, 2002, EUR J ORG CHEM, V2002, P1206