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

[1] 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE (PMEA) EFFECTIVELY INHIBITS RETROVIRUS REPLICATION INVITRO AND SIMIAN IMMUNODEFICIENCY VIRUS-INFECTION IN RHESUS-MONKEYS [J].

BALZARINI, J ;

NAESENS, L ;

SLACHMUYLDERS, J ;

NIPHUIS, H ;

ROSENBERG, I ;

HOLY, A ;

SCHELLEKENS, H ;

DECLERCQ, E .

AIDS, 1991, 5 (01) :21-28

[2]

BALZARINI J, 1992, J BIOL CHEM, V267, P11831

[3] HIV-1-SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS SHOW DIFFERENTIAL ACTIVITY AGAINST HIV-1 MUTANT STRAINS CONTAINING DIFFERENT AMINO-ACID SUBSTITUTIONS IN THE REVERSE-TRANSCRIPTASE [J].

BALZARINI, J ;

KARLSSON, A ;

PEREZPEREZ, MJ ;

VRANG, L ;

WALBERS, J ;

ZHANG, H ;

OBERG, B ;

VANDAMME, AM ;

CAMARASA, MJ ;

DECLERCQ, E .

VIROLOGY, 1993, 192 (01) :246-253

[4] ALPHA,BETA-METHYLENE AND BETA,GAMMA-METHYLENE 5'-PHOSPHONATE DERIVATIVES OF 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE-5'-TRIPHOSPHATE - CORRELATION BETWEEN AFFINITY FOR REVERSE-TRANSCRIPTASE, SUSCEPTIBILITY TO HYDROLYSIS BY PHOSPHODIESTERASES AND ANTI-RETROVIRUS ACTIVITY [J].

BALZARINI, J ;

HERDEWIJN, P ;

PAUWELS, R ;

BRODER, S ;

DECLERCQ, E .

BIOCHEMICAL PHARMACOLOGY, 1988, 37 (12) :2395-2403

[5] RIBONUCLEOSIDE CYCLIC 3',5'-PHOSPHORAMIDATES - SYNTHESIS, STEREOCHEMISTRY, AND CONVERSION INTO RIBONUCLEOSIDE CYCLIC 3',5'-PHOSPHOROTHIOATES AND -[O-18]PHOSPHATES [J].

BARANIAK, J ;

STEC, WJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1645-1656

[6]

BEATON G, 1991, OLIGONUCLEOTIDES ANA, P109

[7]

BOTELHO LHP, 1988, J BIOL CHEM, V263, P5301

[8]

Dahl O., 1991, SULFUR REP, V11, P167

[9] TRIS(TETRA-NORMAL-BUTYLAMMONIUM) HYDROGEN PYROPHOSPHATE - A NEW REAGENT FOR THE PREPARATION OF ALLYLIC PYROPHOSPHATE ESTERS [J].

DIXIT, VM ;

LASKOVICS, FM ;

NOALL, WI ;

POULTER, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1967-1969

[10] NUCLEOSIDE PHOSPHOROTHIOATES [J].

ECKSTEIN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) :4718-+

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