5-(5-BROMOTHIEN-2-YL)-2'-DEOXYURIDINE AND 5-(5-CHLOROTHIEN-2-YL)-2'-DEOXYURIDINE ARE EQUIPOTENT TO (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN THE INHIBITION OF HERPES-SIMPLEX VIRUS TYPE-I REPLICATION

被引：87
|
作者：
WIGERINCK, P [1 ]
PANNECOUQUE, C [1 ]
SNOECK, R [1 ]
CLAES, P [1 ]
DECLERCQ, E [1 ]
HERDEWIJN, P [1 ]
机构：
[1] CATHOLIC UNIV LEUVEN,REGA INST MED RES,MINDERBROEDERSSTR 10,B-3000 LOUVAIN,BELGIUM
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 1991年 / 34卷 / 08期
关键词：
D O I：
10.1021/jm00112a011
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.
引用
收藏
页码：2383 / 2389
页数：7
相关论文
共 50 条
  • [11] GENOTOXIC PROPERTIES OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE (BVDU)
    OSHIRO, Y
    PIPER, CE
    SOELTER, SG
    BALWIERZ, PS
    GARRIOTT, ML
    FUNDAMENTAL AND APPLIED TOXICOLOGY, 1992, 18 (04): : 491 - 498
  • [12] DIFFERENTIATION OF HERPES-SIMPLEX VIRUS TYPE-1 AND TYPE-2 BY SENSITIVITY TO (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    MAYO, DR
    JOURNAL OF CLINICAL MICROBIOLOGY, 1982, 15 (04) : 733 - 736
  • [13] ON THE MECHANISM OF SELECTIVE-INHIBITION OF HERPESVIRUS REPLICATION BY (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    ALLAUDEEN, HS
    KOZARICH, JW
    BERTINO, JR
    DECLERCQ, E
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (05): : 2698 - 2702
  • [14] ORAL (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE IN SEVERE HERPES-ZOSTER
    DECLERCO, E
    DEGREEF, H
    WILDIERS, J
    DEJONGE, G
    DROCHMANS, A
    DESCAMPS, J
    DESOMER, P
    BRITISH MEDICAL JOURNAL, 1980, 281 (6249): : 1178 - 1178
  • [15] HERPES-SIMPLEX VIRUS TYPE-1 THAT EXHIBITS HERPES-SIMPLEX VIRUS TYPE-2 SENSITIVITY TO (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    DOCHERTY, JJ
    DOBSON, AT
    TRIMBLE, JJ
    JENNINGS, BA
    INTERVIROLOGY, 1991, 32 (05) : 308 - 315
  • [16] EFFECT OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE ON SYNTHESIS OF HERPES-SIMPLEX VIRUS TYPE-1-SPECIFIC POLYPEPTIDES
    SIEGEL, SA
    OTTO, MJ
    DECLERCQ, E
    PRUSOFF, WH
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1984, 25 (05) : 566 - 570
  • [17] REGENERATION OF THE ANTIVIRAL DRUG (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE INVIVO
    DESGRANGES, C
    RAZAKA, G
    DROUILLET, F
    BRICAUD, H
    HERDEWIJN, P
    DECLERCQ, E
    NUCLEIC ACIDS RESEARCH, 1984, 12 (04) : 2081 - 2090
  • [18] INFLUENCE OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE ON CORNEAL EPITHELIUM HEALING
    MAUDGAL, PC
    DEKIMPE, N
    DECLERCQ, E
    DESCAMPS, J
    MISSOTTEN, L
    GEYSEN, A
    GRAEFES ARCHIVE FOR CLINICAL AND EXPERIMENTAL OPHTHALMOLOGY, 1982, 218 (05) : 275 - 281
  • [19] (+/-)-CARBOCYCLIC (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE - A POTENT ANTIHERPES AGENT
    COOKSON, RC
    DUDFIELD, PJ
    NEWTON, RF
    RAVENSCROFT, P
    SCOPES, DIC
    CAMERON, JM
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1985, 20 (04) : 375 - 377
  • [20] SYNTHESIS OF 3'-MODIFIED ANALOGS OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE
    DYATKINA, NB
    KRAYEVSKY, AA
    GERMAN, G
    JANTALIPINSKI, M
    LANGEN, P
    YARTSEVA, IV
    BIOORGANICHESKAYA KHIMIYA, 1986, 12 (03): : 408 - 415
12345