Synthesis of (±)-1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides via 'click' cycloaddition

被引：25

作者：

Broggi, Julie ^{[1
,2
]}

Joubert, Nicolas ^{[1
]}

Diez-Gonzalez, Silvia ^{[2
]}

Berteina-Raboin, Sabine ^{[1
]}

Zevaco, Thomas ^{[3
]}

Nolan, Steven P. ^{[2
]}

Agrofoglio, Luigi A. ^{[1
]}

机构：

[1] Univ Orleans, UMR 6005, ICOA, F-45067 Orleans, France

[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[3] Bereich Chem Phys Verfahren, Inst Tech Chem, Forschungszentrum Karlsruhe GmbH, D-7601 Karlsruhe, Germany

来源：

TETRAHEDRON | 2009年 / 65卷 / 06期

关键词：

ANTIVIRAL ACTIVITY; 1,3-DIPOLAR CYCLOADDITION; ANTIBACTERIAL ACTIVITY; ANALOGS; NUCLEOSIDES; AZIDES; CHEMISTRY; REDUCTION; 1,2,3-TRIAZOLES; DERIVATIVES;

D O I：

10.1016/j.tet.2008.11.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1,2,3-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(+/-)-[1,2,3]-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations tip to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox Virus (Brighton strain) in vero cells. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1162 / 1170

页数：9

共 66 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[2]

Agrofoglio L, 1998, ACYCLIC CARBOCYCLIC

[3] Thiosugar nucleosides.: Effect of sulfur in the synthesis of substituted azido-5-thio-D-gluco- and allopryranosyl-N-nucleosides and new isothionucleoside derivatives thereof [J].

Al-Masoudi, NA ;

Al-Soud, YA ;

Schuppler, T .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2005, 24 (03) :237-250

[4] N- and C-acyclic thionuleoside analogues of 1,2,3-triazole [J].

Al-Masoudi, NA ;

Al-Soud, YA ;

Abdul-Zahra, A .

HETEROATOM CHEMISTRY, 2004, 15 (05) :380-387

[5] New glycosyl-(carboxamide)-1,2,3-triazole-N-nucleosides:: Synthesis and antitumor activity [J].

Al-Masoudi, NA ;

Al-Soud, YA .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2002, 21 (4-5) :361-375

[6] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[7]

[Anonymous], 1 3 DIPOLAR CYCLOADD

[8] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].

Appukkuttan, P ;

Dehaen, W ;

Fokin, VV ;

Van der Eycken, E .

ORGANIC LETTERS, 2004, 6 (23) :4223-4225

[9] Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections [J].

Baker, R ;

Bray, M ;

Huggins, JW .

ANTIVIRAL RESEARCH, 2003, 57 (1-2) :13-23

[10] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

← 1 2 3 4 5 6 7 →