Efficient synthesis of N-4 alkyl derivatives of 2′,3′-dideoxycytidine (ddC).

被引：5

作者：

Dechaux, E ^{[1
]}

Pontikis, R ^{[1
]}

Monneret, C ^{[1
]}

机构：

[1] Inst Curie, Sect Rech, UMR 176 CNRS IC, F-75231 Paris 05, France

来源：

NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 01期

关键词：

D O I：

10.1080/07328319908045588

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：

The C-4 triisopropylphenylsulfonyl (TPS) group of the 2',3'-dideoxyuridine derivative 2 is readily displaced in sine by nitrogen nucleophiles forming N-4 substituted ddC in acceptable yields.

引用

页码：1 / 4

页数：4

共 13 条

[1] Mechanisms of nucleoside analog antiviral activity and resistance during human immunodeficiency virus reverse transcription [J].

Arts, EJ ;

Wainberg, MA .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1996, 40 (03) :527-540

[2] SYNTHESIS OF NOVEL POLYCYCLIC NUCLEOSIDE ANALOGS, INCORPORATION INTO OLIGODEOXYNUCLEOTIDES, AND INTERACTION WITH COMPLEMENTARY SEQUENCES [J].

BISCHOFBERGER, N ;

MATTEUCCI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :3041-3046

[3] TOWARD IMPROVED ANTI-HIV CHEMOTHERAPY - THERAPEUTIC STRATEGIES FOR INTERVENTION WITH HIV-INFECTIONS [J].

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2491-2517

[4] Development of resistance of human immunodeficiency virus (HIV) to anti-HIV agents: how to prevent the problem? [J].

DeClercq, E .

INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 1997, 9 (01) :21-36

[5] SYNTHESIS OF 4-SUBSTITUTED PYRIMIDINE 2',3'-DIDEOXYNUCLEOSIDES [J].

DENAPOLI, L ;

MESSERE, A ;

MONTESARCHIO, D ;

PICCIALLI, G ;

SANTACROCE, C .

NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (08) :1719-1728

[6] PREPARATION OF 1-(2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE (D4T)1 AND 2',3'-DIDEOXYADENOSINE (DDA) - GENERAL-METHODS FOR THE SYNTHESIS OF 2',3'-OLEFINIC AND 2',3'-DIDEOXY NUCLEOSIDE ANALOGS ACTIVE AGAINST HIV [J].

MANSURI, MM ;

STARRETT, JE ;

WOS, JA ;

TORTOLANI, DR ;

BRODFUEHRER, PR ;

HOWELL, HG ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4780-4785

[7] ONE-STEP HALOGENATION AT 2'-POSITION OF URIDINE, AND RELATED REACTIONS OF CYTIDINE AND N4-ACETYLCYTIDINE [J].

MARUMOTO, R ;

HONJO, M .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (01) :128-134

[8] Convenient intermediates for the preparation of C-4 modified derivatives of pyrimidine nucleosides [J].

Miah, A ;

Reese, CB ;

Song, QL .

NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (1-2) :53-65

[9] Synthesis of 5-methyl-2'-O-deoxycytidine analogs to determine monoclonal antibody specificity in the recognition of the 6-(p-bromobenzoylamino)caproyl radical. [J].

RodriguezTanty, C ;

HigginsonClarke, D ;

Hernandez, M ;

Perez, R ;

VelezCastro, H ;

Riveron, AM ;

Macias, A .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1997, 16 (04) :455-467

[10] Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane. [J].

Saladino, R ;

Mincione, E ;

Crestini, C ;

Mezzetti, M .

TETRAHEDRON, 1996, 52 (19) :6759-6780

← 1 2 →