A 'click chemistry' approach to the efficient synthesis of modified nucleosides and oligonucleotides for PET imaging

被引:23
作者
James, Damien [1 ]
Escudier, Jean-Marc [2 ]
Amigues, Eric [1 ]
Schulz, Juergen [3 ]
Vitry, Christiane [1 ]
Bordenave, Thomas [1 ]
Szlosek-Pinaud, Magali [1 ]
Fouquet, Eric [1 ]
机构
[1] Univ Bordeaux, CNRS, UMR 5255, Inst Mol Sci, F-33405 Talence, France
[2] Univ Toulouse 3, CNRS, UMR 5068, LSPCMIB, F-31062 Toulouse, France
[3] Univ Bordeaux, CNRS, UMR 5231, LIMF, F-33076 Bordeaux, France
关键词
REAGENTS; C-11;
D O I
10.1016/j.tetlet.2009.12.120
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Different thymidine derivatives bearing either an iodoaryl moiety at the 5' position or a dialkylsilyl group at the 3' position have been efficiently synthesized as precursors for carbon-11 or fluorine-18 labeling, respectively. Furthermore, iodoarylated thymidine derivatives have been incorporated into oligonucleotides giving an original way to label them with carbon-11. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1230 / 1232
页数:3
相关论文
共 27 条
[1]  
Allard M, 2008, CURR MED CHEM, V15, P235
[2]  
Banuls V, 2001, EUR J ORG CHEM, V2001, P4693, DOI 10.1002/1099-0690(200112)2001:24<4693::AID-EJOC4693>3.0.CO
[3]  
2-J
[4]   Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines [J].
Banuls, V ;
Escudier, JM .
TETRAHEDRON, 1999, 55 (18) :5831-5838
[5]   Tetra- and monoorganotin reagents in palladium-mediated cross-coupling reactions for the labeling with carbon-11 of PET tracers [J].
Bourdier, Thomas ;
Huiban, Michael ;
Huet, Aline ;
Sobrio, Franck ;
Fouquet, Eric ;
Perrio, Cecile ;
Barre, Louisa .
SYNTHESIS-STUTTGART, 2008, 6 (06) :978-984
[6]   Silver(I) oxide mediated highly selective monotosylation of symmetrical diols.: Application to the synthesis of polysubstituted cyclic ethers [J].
Bouzide, A ;
Sauvé, G .
ORGANIC LETTERS, 2002, 4 (14) :2329-2332
[7]   ON THE COMMUNICATION OF CHIRALITY FROM FURANOSE AND PYRANOSE RINGS TO MONOSACCHARIDE SIDE-CHAINS - ANOMALOUS RESULTS IN THE GLUCOSE SERIES [J].
DANISHEFSKY, SJ ;
DENINNO, MP ;
PHILLIPS, GB ;
ZELLE, RE ;
LARTEY, PA .
TETRAHEDRON, 1986, 42 (11) :2809-2819
[8]   Working against time: Rapid radiotracer synthesis and imaging the human brain [J].
Fowler, JS ;
Wolf, AP .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (04) :181-188
[9]  
FOWLER JS, 1986, POSITRON EMISSION TO, pCH9
[10]   Stille cross-coupling of activated alkyltin reagents under "Ligandless" conditions [J].
Herve, A ;
Rodriguez, AL ;
Fouquet, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1953-1956