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

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 10期

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

页码：1222 / 1228

页数：7

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