Alkyne-azide click chemistry mediated carbanucleosides synthesis

被引:20
作者
Broggi, Julie [1 ]
Joubert, Nicolas [1 ]
Aucagne, Vincent [1 ]
Berteina-Raboin, Sabine [1 ]
Diez-Gonzalez, S. [2 ]
Nolan, Steve [2 ]
Topalis, Dimitri [3 ]
Deville-Bonne, Dominique [3 ]
Balzarini, Jan [4 ]
Neyts, Johan [4 ]
Andrei, Graciela [4 ]
Snoeck, Robert [4 ]
Agrofoglio, Luigi A. [1 ]
机构
[1] Univ Orleans, Inst Chim Organ & Analyt, UMR 6005, Orleans, France
[2] Inst Chem Res Catalonia ICIQ, Tarragona, Spain
[3] Univ Paris 06, Lab Enzymol & Mol Fonct, FRE CNRS 2852, Paris, France
[4] Katholieke Univ Leuven, Rega Inst Med Res, Dept Microbiol & Immunol, B-3000 Louvain, Belgium
关键词
click chemistry; Huisgen cycloaddition; carbanucleosides; alkyne-azide;
D O I
10.1080/15257770701534139
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
Hitherto unknown 1,4-disubstituted-[1,2,3]-triazolo-4',4'-dihydroxymethyl-3'-deoxycarbanucleosides were synthesized based on a "click approach." Various alkynes were introduced on a key azido intermediate by the "click" 1,3-dipolar Huisgen cycloaddition. Their antiviral activities and cellular toxicities were evaluated on vaccinia virus. None of the synthesized compounds exhibited a significant antiviral activity.
引用
收藏
页码:1391 / 1394
页数:4
相关论文
共 8 条
[1]
An overview of diazine nucleoside analogues [J].
Agrofoglio, LA .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (03) :333-362
[2]
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
[3]
Treating HCV with ribavirin analogues and ribavirin-like molecules [J].
Gish, RG .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2006, 57 (01) :8-13
[4]
Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates [J].
Himo, F ;
Lovell, T ;
Hilgraf, R ;
Rostovtsev, VV ;
Noodleman, L ;
Sharpless, KB ;
Fokin, VV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :210-216
[5]
Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD
[6]
Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[7]
2-4
[8]
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides [J].
Tornoe, CW ;
Christensen, C ;
Meldal, M .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3057-3064