Indirect coupling of the 2(1,H)-pyrazinone scaffold with various (oligo)-saccharides via "click chemistry":: en route towards glycopeptidomimetics

被引:29
作者
Ermolat'ev, D [1 ]
Dehaen, W [1 ]
Van der Eycken, E [1 ]
机构
[1] Univ Louvain, Dept Chem, Synth Organ Lab, B-3001 Louvain, Belgium
来源
QSAR & COMBINATORIAL SCIENCE | 2004年 / 23卷 / 10期
关键词
glycosyl azides; 1,2,3-triazoles; 2(1H)-pyrazinone; click chemistry; 1,3-dipolar cycloaddition;
D O I
10.1002/qsar.200420049
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The indirect coupling via a 1,2,3-triazole ring system, of the 2(1H)-pyrazinone scaffold with various saccharides is described. A microwave-enhanced Cu(I)-catalyzed Huisgen [2 + 3] dipolar cycloaddition reaction is applied. This opens the way for the generation of an interesting new class of glycopeptidomimetics.
引用
收藏
页码:915 / 918
页数:4
相关论文
共 18 条
[1]   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
[2]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[3]   Synthesis of a conformationally restricted dipeptide analogue and its evaluation as a β-turn mimic [J].
De Borggraeve, WM ;
Rombouts, FJR ;
Van der Eycken, EV ;
Toppet, SM ;
Hoornaert, GJ .
TETRAHEDRON LETTERS, 2001, 42 (33) :5693-5695
[4]   Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1,3-dipolar cycloaddition reactions [J].
Dondoni, A ;
Giovannini, PP ;
Massi, A .
ORGANIC LETTERS, 2004, 6 (17) :2929-2932
[5]  
Dondoni A, 2001, SYNTHESIS-STUTTGART, P2129
[6]   PREFERRED CONFORMATION OF C-GLYCOSIDES .10. SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF CARBON TRISACCHARIDES [J].
HANEDA, T ;
GOEKJIAN, PG ;
KIM, SH ;
KISHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :490-498
[7]   Microwave-enhanced transition metal-catalyzed decoration of 2(1H)-pyrazinone scaffolds [J].
Kaval, Nadya ;
Bisztray, Katalin ;
Dehaen, Wim ;
Kappe, C. Oliver ;
Van der Eycken, Erik .
MOLECULAR DIVERSITY, 2003, 7 (2-4) :125-133
[8]   Expedient synthesis of triazole-linked glycosyl amino acids and peptides [J].
Kuijpers, BHM ;
Groothuys, S ;
Keereweer, AR ;
Quaedflieg, PJLM ;
Blaauw, RH ;
van Delft, FL ;
Rutjes, FPJT .
ORGANIC LETTERS, 2004, 6 (18) :3123-3126
[9]  
LARGE DG, 1997, GLYCOPEPTIDES RELATE
[10]  
NAJIM AA, 2002, TETRAHEDRON LETT, V43, P4021