One-pot click synthesis of 1,2,3-triazole-embedded unsaturated uracil derivatives and hybrids of 1,5-and 2,5-disubstituted tetrazoles and pyrimidines

被引:15
作者
Kristafor, Svjetlana [1 ]
Bistrovic, Andrea [1 ]
Plavec, Janez [2 ,3 ,4 ]
Makuc, Damjan [2 ,3 ]
Martinovic, Tamara [5 ]
Pavelic, Sandra Kraljevic [5 ]
Raic-Malic, Silvana [1 ]
机构
[1] Univ Zagreb, Fac Chem Engn & Technol, Dept Organ Chem, HR-10000 Zagreb, Croatia
[2] Slovenian NMR Ctr, Natl Inst Chem, SI-1000 Ljubljana, Slovenia
[3] EN FIST Ctr Excellence, SI-1000 Ljubljana, Slovenia
[4] Univ Ljubljana, Fac Chem & Chem Technol, SI-1000 Ljubljana, Slovenia
[5] Univ Rijeka, Dept Biotechnol, HR-51000 Rijeka, Croatia
关键词
1,2,3-Triazoles; 1,5-and 2,5-disubstituted tetrazoles; Antitumor activity; Click chemistry; One-pot; BIOLOGICAL EVALUATION; 1,3-DIPOLAR CYCLOADDITION; CATALYZED SYNTHESIS; DESIGN; CHEMISTRY; ANALOGS; ACID; NUCLEOSIDE; AZIDES; NUCLEOTIDE;
D O I
10.1016/j.tetlet.2015.01.152
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel conformationally restricted pyrimidine derivatives with a 1,2,3-triazolyl scaffold bound via Z- and E-2-butenyl spacers were prepared by Cu(I)-catalyzed click chemistry via a one-pot, multi-step reaction under microwave irradiation, while 1,5- and 2,5-disubstituted tetrazoles were synthesized by convenient, environmentally friendly click synthesis and subsequently by N-alkylation of 5-substituted 1H-tetrazoles. Among all the tested compounds, the N-1,N-3-disubstituted olefinic uracil derivative showed the highest antiproliferative effects. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1222 / 1228
页数:7
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