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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.
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页码:1222 / 1228
页数:7
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