THE SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME 4'-THIO-2'-DEOXY NUCLEOSIDE ANALOGS

被引：160
作者：
DYSON, MR [1 ]
COE, PL [1 ]
WALKER, RT [1 ]
机构：
[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 1991年 / 34卷 / 09期
关键词：
D O I：
10.1021/jm00113a016
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Starting from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (4), the following 2'-deoxy nucleoside analogues have been synthesized: 4'-thiothymidine (8), 3'-azido-4'-thio-deoxythymidine (10), and (E)-5-(2-bromovinyl)-4'-thio-2'-deoxyuridine (22). The first compound is toxic, the second is not toxic nor has detectable biological activity, and the third is not toxic and has significant activity against some herpesviruses.
引用
收藏
页码：2782 / 2786
页数：5
相关论文
共 17 条
  • [1] THE SYNTHESIS AND ANTIVIRAL PROPERTIES OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE-RELATED COMPOUNDS
    ASHWELL, M
    JONES, AS
    KUMAR, A
    SAYERS, JR
    WALKER, RT
    SAKUMA, T
    DECLERCQ, E
    [J]. TETRAHEDRON, 1987, 43 (20) : 4601 - 4608
  • [2] SYNTHESIS OF SOME 5-HALOGENOVINYL DERIVATIVES OF URACIL AND THEIR CONVERSION INTO 2'-DEOXYRIBONUCLEOSIDES
    BARR, PJ
    JONES, AS
    VERHELST, G
    WALKER, RT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06): : 1665 - 1670
  • [3] BUCHANAN JG, 1980, J CHEM SOC P1, P2667
  • [4] SYNTHESIS AND ANTIVIRAL PROPERTIES OF 5-VINYLPYRIMIDINE NUCLEOSIDE ANALOGS
    DECLERCQ, E
    WALKER, RT
    [J]. PHARMACOLOGY & THERAPEUTICS, 1984, 26 (01) : 1 - 44
  • [5] DECLERCQ E, 1979, P NATL ACAD SCI USA, V76, P2947, DOI 10.1073/pnas.76.6.2947
  • [6] PHOSPHOROLYSIS OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE (BVDU) AND OTHER 5-SUBSTITUTED-2'-DEOXYURIDINES BY PURIFIED HUMAN THYMIDINE PHOSPHORYLASE AND INTACT BLOOD-PLATELETS
    DESGRANGES, C
    RAZAKA, G
    RABAUD, M
    BRICAUD, H
    BALZARINI, J
    DECLERCQ, E
    [J]. BIOCHEMICAL PHARMACOLOGY, 1983, 32 (23) : 3583 - 3590
  • [7] DYSON MR, IN PRESS CARBOHYDR R
  • [8] ALTERNATIVE SYNTHESIS OF ANOMERIC METHYL 2-DEOXY-4-THIO-D-ERYTHRO-PENTOFURANOSIDES
    FU, YL
    BOBEK, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) : 3831 - 3834
  • [9] FU YL, 1978, NUCLEIC ACID CHEM, P317
  • [10] NUCLEOTIDE SYNTHESIS .4. PHOSPHORYLATED 3'-AMINO-3'-DEOXYTHYMIDINE AND 5'-AMINO-5'-DEOXYTHYMIDINE AND DERIVATIVES
    GLINSKI, RP
    KHAN, MS
    KALAMAS, RL
    SPORN, MB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (25) : 4299 - 4305
12