Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides

被引：96

作者：

Rahim, SG ^{[1
]}

Trivedi, N ^{[1
]}

BogunovicBatchelor, MV ^{[1
]}

Hardy, GW ^{[1
]}

Mills, G ^{[1
]}

Selway, JWT ^{[1
]}

Snowden, W ^{[1
]}

Littler, E ^{[1
]}

Coe, PL ^{[1
]}

Basnak, I ^{[1
]}

Whale, RF ^{[1
]}

Walker, RT ^{[1
]}

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1996年 / 39卷 / 03期

关键词：

D O I：

10.1021/jm950029r

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

引用

页码：789 / 795

页数：7

共 42 条

[1] SYNTHESIS OF SOME 5-HALOGENOVINYL DERIVATIVES OF URACIL AND THEIR CONVERSION INTO 2'-DEOXYRIBONUCLEOSIDES [J].

BARR, PJ ;

JONES, AS ;

VERHELST, G ;

WALKER, RT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1665-1670

[2] THE SYNTHESIS OF SOME 5-SUBSTITUTED AND 5,6-DISUBSTITUTED 2'-DEOXYURIDINES [J].

BASNAK, I ;

BALKAN, A ;

COE, PL ;

WALKER, RT .

NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (1-3) :177-196

[3] NUCLEIC-ACIDS COMPONENTS AND THEIR ANALOGS .199. SYNTHESIS OF URACILS SUBSTITUTED IN THE POSITION-5 OR POSITION-5,6 WITH ALKYL OR CYCLOALKYL GROUPS AND THEIR UV SPECTRA [J].

BASNAK, I ;

FARKAS, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1979, 44 (08) :2426-2437

[4] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 4'-THIO ANALOGS OF ANTIBIOTIC TOYOCAMYCIN [J].

BOBEK, M ;

BLOCH, A ;

WHISTLER, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (02) :168-&

[5] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-(2,2-DIFLUOROVINYL)-2'-DEOXYURIDINE [J].

BOBEK, M ;

KAVAI, I ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1494-1497

[6] PREPARATION AND ACTIVITY OF 4'-THIO DERIVATIVES OF SOME 6-SUBSTITUTED PURINE NUCLEOSIDES [J].

BOBEK, M ;

WHISTLER, RL ;

BLOCK, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (03) :411-&

[7] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-FLUORO-4'-THIOURIDINE AND SOME RELATED NUCLEOSIDES [J].

BOBEK, M ;

BLOCH, A ;

PARTHASARATHY, R ;

WHISTLER, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (08) :784-787

[8] PYRIMIDINES .11. SYNTHESIS OF 5-HYDROXYPYRIMIDINE AND RELATED COMPOUNDS [J].

CHESTERFIELD, JH ;

MCOMIE, JFW ;

TUTE, MS .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (NOV) :4590-4596

[9] SYNTHESIS AND ANTIVIRAL PROPERTIES OF SOME 2'-DEOXY-5-(FLUOROALKENYL)URIDINES [J].

COE, PL ;

HARNDEN, MR ;

JONES, AS ;

NOBLE, SA ;

WALKER, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (11) :1329-1334

[10] GROWTH-INHIBITION BY ACYCLOGUANOSINE OF HERPESVIRUSES ISOLATED FROM HUMAN INFECTIONS [J].

CRUMPACKER, CS ;

SCHNIPPER, LE ;

ZAIA, JA ;

LEVIN, MJ .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :642-645

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