Synthesis of 3′-O2-(azaheterocycle)-thymidines

被引:5
作者
Prestat, G
Dubreuil, D
Adjou, A
Pradère, JP
Lebreton, J
Evers, M
Henin, Y
机构
[1] Fac Sci & Tech, Organ Synth Lab, CNRS, UMR 6513, F-44322 Nantes 3, France
[2] Fac Sci & Tech, Chim Organ Struct Lab, Abidjan, Cote Ivoire
[3] Rhone Poulenc Rorer, Ctr Rech Vitry Alfortville, F-94403 Vitry, France
关键词
3 '-modified thymidine; thioacylamidines; thioacylimines; 4H-1,3-thiazines; thiazoles; thiazol-2-ine; 1-thia-3-azabutadienes;
D O I
10.1080/15257770008035021
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of 3'-O-2-(azaheterocycle)-thymidines is presented from 1-thia-3-aza-1,3-butadiene precursors (N-thioacylamidines). A variety of heterocycles is accessible using the dienic, the electrophilic or the nucleophilic reactivity of these thia-azabutadiene systems. 3'-O-2-(azaheterocycle)-thymidine analogues are regarded as potential substrates to interfere with the DNA-polymerization process.
引用
收藏
页码:735 / 748
页数:14
相关论文
共 57 条
[1]   ELECTROCHEMICAL REDUCTION OF 4H-1,3-THIAZINES - SYNTHESIS OF SUBSTITUTED PYRROLES AND (OR) 6H-1,3-THIAZINES [J].
ABOUELFIDA, A ;
PRADERE, JP ;
JUBAULT, M ;
TALLEC, A .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (01) :14-20
[2]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[3]  
Alvarez R, 1998, ANTIVIR CHEM CHEMOTH, V9, P333
[4]   HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 (HIV-1) STRAINS SELECTED FOR RESISTANCE AGAINST THE HIV-1-SPECIFIC [2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOLE-2'',2''-DIOXIDE)]-BETA-D-PENTOFURANOSYL (TSAO) NUCLEOSIDE ANALOGS RETAIN SENSITIVITY TO HIV-1-SPECIFIC NONNUCLEOSIDE INHIBITORS [J].
BALZARINI, J ;
KARLSSON, A ;
VANDAMME, AM ;
PEREZPEREZ, MJ ;
ZHANG, H ;
VRANG, L ;
OBERG, B ;
BACKBRO, K ;
UNGE, T ;
SANFELIX, A ;
VELAZQUEZ, S ;
CAMARASA, MJ ;
DECLERCQ, E .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6952-6956
[5]  
BALZARINI J, 1988, MOL PHARMACOL, V33, P243
[6]  
Boger D. L., 1987, HETERO DIELS ALDER M
[7]  
CAMARASA MJ, 1997, J SPEC PUBL R SOC CH, V198, P259
[8]   SUBSTITUTED 1-THIA-3-AZA-1,3-BUTADIENE - DIELS-ALDER REACTION WITH METHYLACRYLATE - DETERMINATION OF ACTIVATION PARAMETERS [J].
CHEHNA, M ;
PRADERE, JP ;
QUINIOU, H ;
LEBOTLAN, D ;
TOUPET, L .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 42 (1-2) :15-19
[9]   PHOTOCHEMISTRY OF DI(DEOXYRIBONUCLEOSIDE) METHYLPHOSPHONATES CONTAINING N-3-METHYL-4-THIOTHYMINE [J].
CLIVIO, P ;
FOURREY, JL ;
SZABO, T ;
STAWINSKI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7273-7283
[10]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+