A FACILE SYNTHESIS OF 4'-THIO-2'-DEOXYPYRIMIDINE NUCLEOSIDES AND PRELIMINARY STUDIES ON THEIR PROPERTIES

被引：30

作者：

HUANG, BG ^{[1
]}

HUI, YZ ^{[1
]}

机构：

[1] CHINESE ACAD SCI,SHANGHAI INST ORGAN CHEM,SHANGHAI 200032,PEOPLES R CHINA

来源：

NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 02期

关键词：

D O I：

10.1080/07328319308021200

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：

Several 4'-thio-2'-deoxypyrimidine nucleosides were synthesized from 2-deoxy-D-ribose via 7 steps. The 4-thio-nucleosides were obtained by reaction of the corresponding trimethylsilylated pyrimidine bases with 4-thiosugar(6), which has been synthesized in one step by treatment of 3,5-di-O-benzyl-2-deoxy-D-ribose dibenzyldithioacetal(4) with the Ph3P-I2-Im system. The chemical stability of 4'-thio-2'-deoxythymidine is also described. 5-Fluoro-2'-deoxyuridine (5-FDUR), 5-iodo-2'-deoxyuridine(5-IDUR) and their 4'-thio-analogs 8b, 8c were evaluated for antitumor activity. 5-Fluoro-4'-thio-2'-deoxyuridine(8b) was more inhibitory than 5-FDUR, especially at a concentration of 1mug/ml.

引用

页码：139 / 147

页数：9

共 8 条

[1] THE SYNTHESIS AND ANTIVIRAL PROPERTIES OF E-5-(2-BROMOVINYL)-4'-THIO-2'-DEOXYURIDINE [J].

DYSON, MR ;

COE, PL ;

WALKER, RT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (10) :741-742

[2] ALTERNATIVE SYNTHESIS OF ANOMERIC METHYL 2-DEOXY-4-THIO-D-ERYTHRO-PENTOFURANOSIDES [J].

FU, YL ;

BOBEK, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) :3831-3834

[3]

FU YL, 1978, NUCLEIC ACID CHEM, P317

[4] SOME ASPECTS OF REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE REACTIONS IN CARBOHYDRATE-CHEMISTRY [J].

GAREGG, PJ .

PURE AND APPLIED CHEMISTRY, 1984, 56 (07) :845-858

[5] SYNTHESIS AND PROPERTIES OF NUCLEOTIDES CONTAINING 4-THIO-D-RIBOFURANOSE [J].

HOFFMAN, DJ ;

WHISTLER, RL .

BIOCHEMISTRY, 1970, 9 (11) :2367-&

[6] 4-O-BENZYL-2,3-O-ISOPROPYLIDENE-L-THREOSE - A USEFUL BUILDING BLOCK FOR STEREOSELECTIVE SYNTHESIS OF MONOSACCHARIDES [J].

MUKAIYAMA, T ;

SUZUKI, K ;

YAMADA, T ;

TABUSA, F .

TETRAHEDRON, 1990, 46 (01) :265-276

[7]

OGAWA T, 1981, CARBOHYDR RES C, V6, P93

[8] PREPARATION AND ANTITUMOR ACTIVITY OF 4'-THIO ANALOGS OF 2,2'-ANHYDRO-1-BETA-D-ARABINOFURANOSYLCYTOSINE [J].

OTOTANI, N ;

WHISTLER, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (05) :535-537

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