THE SYNTHESIS OF NUCLEOSIDE 5'-O-(1,1-DITHIOTRIPHOSPHATES)

被引：30

作者：

OKRUSZEK, A ^{[1
]}

OLESIAK, M ^{[1
]}

BALZARINI, J ^{[1
]}

机构：

[1] CATHOLIC UNIV LEUVEN,REGA INST MED RES,B-3000 LOUVAIN,BELGIUM

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1994年 / 37卷 / 22期

关键词：

D O I：

10.1021/jm00048a021

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Appropriately protected nucleoside 5'-O-(2-thio-1,3,2-dithiaphospholanes) react with inorganic pyrophosphate in the presence of a strong base catalyst (DBU) to give nucleoside 5'-O-(1,1-dithiotriphosphates) 1a-g. The latter compounds, including an AZT analogue, show modest antivirial activity against HIV-1 and HTV-8 replication in CEM cells. The AZT and deoxyadenosine derivatives were found to be inhibitors of HIV reverse transcriptase.

引用

页码：3850 / 3854

页数：5

共 29 条

[11] PHOSPHOROTHIOATES IN MOLECULAR-BIOLOGY [J].

ECKSTEIN, F ;

GISH, G .

TRENDS IN BIOCHEMICAL SCIENCES, 1989, 14 (03) :97-100

[12] NUCLEOSIDE PHOSPHOROTHIOATES [J].

ECKSTEIN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (18) :4292-&

[13] NUCLEOSIDE PHOSPHOROTHIOATES [J].

ECKSTEIN, F .

ANNUAL REVIEW OF BIOCHEMISTRY, 1985, 54 :367-402

[14] SIDE-CHAIN DERIVATIVES OF BIOLOGICALLY-ACTIVE NUCLEOSIDES .1. SIDE-CHAIN ANALOGS OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT) [J].

HIEBL, J ;

ZBIRAL, E ;

BALZARINI, J ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) :3016-3023

[15]

JONES RA, 1984, OLIGONUCLEOTIDE SYNT, P23

[16]

KABACHNIK MI, 1956, IAN SSSR KH, P790

[17] STEREOSPECIFIC SYNTHESIS OF GUANOSINE 5'-0-(1,2-DITHIOTRIPHOSPHATES) [J].

LUDWIG, J ;

ECKSTEIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5860-5865

[18] SYNTHESIS OF NUCLEOSIDE 5'-O-(1,3-DITHIOTRIPHOSPHATES) AND 5'-O-(1,1-DITHIOTRIPHOSPHATES) [J].

LUDWIG, J ;

ECKSTEIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1777-1783

[19] RAPID AND EFFICIENT SYNTHESIS OF NUCLEOSIDE 5'-O-(1-THIOTRIPHOSPHATES), 5'-TRIPHOSPHATES AND 2',3'-CYCLOPHOSPHOROTHIOATES USING 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE [J].

LUDWIG, J ;

ECKSTEIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :631-635

[20] GENERAL AND EFFICIENT ROUTE TO PHOSPHORODITHIOATE ANALOGS OF NATURALLY-OCCURRING LIPIDS [J].

MARTIN, SF ;

WAGMAN, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5897-5899

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