Simple and efficient routes for the preparation of isoxazolidinyl nucleosides containing cytosine and 5-methyl-cytosine as new potential anti-HIV drugs

被引：37

作者：

Colacino, E ^{[1
]}

Converso, A ^{[1
]}

Liguori, A ^{[1
]}

Napoli, A ^{[1
]}

Siciliano, C ^{[1
]}

Sindona, G ^{[1
]}

机构：

[1] Univ Calabria, Dipartimento Chim, I-87030 Arcavacata Di Rende, CS, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 40期

关键词：

antivirals; modified nucleosides; isoxazolidinyl nucleosides; cycloadditions; isoxazolidines;

D O I：

10.1016/S0040-4020(01)00813-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rapid and convenient large-scale strategy for the synthesis of some new isoxazolidinyl nucleosides, as potential antiviral drugs, is reported. In particular, a multistep methodology based either on the 1,3-dipolar cycloaddition approach or on a slight modification of the convertible nucleoside concept was exploited in the preparation of 4'-aza-2',3'-dideoxynucleoside, analogues containing cytosine and 5-methyl-cytosine. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8551 / 8557

页数：7

共 30 条

[1] A chemical method for site-specific modification of RNA: The convertible nucleoside approach [J].

Allerson, CR ;

Chen, SL ;

Verdine, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) :7423-7433

[2]

Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis

[3] Stereoselective synthesis of 2′-amino-2′,3′-dideoxynucleosides by nitrone 1,3-dipolar cycloaddition:: A new efficient entry toward d4T and its 2-methyl analogue [J].

Chiacchio, U ;

Rescifina, A ;

Iannazzo, D ;

Romeo, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :28-36

[4] Homochiral α-D- and β-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition [J].

Chiacchio, U ;

Corsaro, A ;

Gumina, G ;

Rescifina, A ;

Iannazzo, D ;

Piperno, A ;

Romeo, G ;

Romeo, R .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9321-9327

[5]

CONVERSO A, 1998, SYNTHESIS MODIFIED 2, V2, P17

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

DECLERCQ, E .

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

[7] HIV INHIBITORS TARGETED AT THE REVERSE-TRANSCRIPTASE [J].

DECLERCQ, E .

AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (02) :119-137

[8] ANTIVIRAL ACTIVITY SPECTRUM AND TARGET OF ACTION OF DIFFERENT CLASSES OF NUCLEOSIDE ANALOGS [J].

DECLERCQ, E .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1994, 13 (6-7) :1271-1295

[9] 4-(1,2,4-TRIAZOL-1-YL) AND 4-(3-NITRO-1,2,4-TRIAZOL-1-YL)-1-(BETA-D-2,3,5-TRI-O-ACETYLARABINOFURANOSYL)PYRIMIDIN-2(1H)-ONES - VALUABLE INTERMEDIATES IN THE SYNTHESIS OF DERIVATIVES OF "1-(BETA-D-ARABINOFURANOSYL)CYTOSINE (ARA-C) [J].

DIVAKAR, KJ ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05) :1171-1176

[10] Synthesis of two 6-N-protected 9-N-vinyladenines as dipolarophiles in the synthesis of modified nucleosides [J].

Giglio, G ;

Napoli, A ;

Leggio, A ;

Liguori, A ;

Procopio, A ;

Siciliano, C ;

Sindona, G .

SYNTHETIC COMMUNICATIONS, 1996, 26 (22) :4211-4217

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