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：88

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

页码：2383 / 2389

页数：7

共 19 条

[1] ON THE MECHANISM OF SELECTIVE-INHIBITION OF HERPESVIRUS REPLICATION BY (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE [J].

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

[2] 5-QUINONE DERIVATIVES OF 2'-DEOXYURIDINE 5'-PHOSPHATE - INHIBITION AND INACTIVATION OF THYMIDYLATE SYNTHASE, ANTITUMOR CELL, AND ANTIVIRAL STUDIES [J].

ALRAZZAK, LA ;

SCHWEPLER, D ;

DECEDUE, CJ ;

BALZARINI, J ;

DECLERCQ, E ;

MERTES, MP .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :409-419

[3] STEREOSELECTIVE SYNTHESIS OF ANOMERS OF 5-SUBSTITUTED 2'-DEOXYURIDINES [J].

AOYAMA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2073-2077

[4] UNSYMMETRICAL HETEROBIARYL SYNTHESIS - A HIGHLY EFFICIENT PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HETEROARYL TRIALKYLSTANNANES WITH ARYL HALIDES [J].

BAILEY, TR .

TETRAHEDRON LETTERS, 1986, 27 (37) :4407-4410

[5]

BALZARINI J, 1990, MOL PHARMACOL, V37, P402

[6] A SYNTHESIS OF 2-(2-PYRIDINYL)IMIDAZOLES AND 4(5)-(2-PYRIDINYL)IMIDAZOLES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS [J].

BELL, AS ;

ROBERTS, DA ;

RUDDOCK, KS .

TETRAHEDRON LETTERS, 1988, 29 (39) :5013-5016

[7] SYNTHESIS OF 5-ARYLURIDINES AND 5-ARYL-2'-DEOXYURIDINES [J].

CRISP, GT ;

MACOLINO, V .

SYNTHETIC COMMUNICATIONS, 1990, 20 (03) :413-422

[8] SYNTHESIS AND ANTIVIRAL PROPERTIES OF 5-VINYLPYRIMIDINE NUCLEOSIDE ANALOGS [J].

DECLERCQ, E ;

WALKER, RT .

PHARMACOLOGY & THERAPEUTICS, 1984, 26 (01) :1-44

[9] COMPARATIVE EFFICACY OF ANTIHERPES DRUGS AGAINST DIFFERENT STRAINS OF HERPES-SIMPLEX VIRUS [J].

DECLERCQ, E ;

DESCAMPS, J ;

VERHELST, G ;

WALKER, RT ;

JONES, AS ;

TORRENCE, PF ;

SHUGAR, D .

JOURNAL OF INFECTIOUS DISEASES, 1980, 141 (05) :563-574

[10] ANTIVIRAL ACTIVITY OF 5-SUBSTITUTED PYRIMIDINE NUCLEOSIDE ANALOGS [J].

DECLERCQ, E .

PURE AND APPLIED CHEMISTRY, 1983, 55 (04) :623-636

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