Design, synthesis, and biological evaluation of new 2′-deoxy-2′-fluoro-4′-triazole cytidine nucleosides as potent antiviral agents

被引：46
|
作者：
Wu, Jie [1 ]
Yu, Wenquan [1 ]
Fu, Leixia [1 ]
He, Wu [1 ]
Wang, Yao [1 ]
Chai, Baoshan [1 ]
Song, Chuanjun [1 ]
Chang, Junbiao [1 ]
机构：
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 63卷
基金：
中国博士后科学基金; 美国国家科学基金会;
关键词：
2 '-Deoxy-2 '-fluoro-4 '-triazole nucleosides; Anti-HIV activity; Nucleoside reverse transcriptase inhibitor (NRTI); Anti-HBV activity; HEPATITIS-B-VIRUS; CLICK CHEMISTRY; CHEMICAL-SYNTHESIS; HIV-1; PROTEASE; C-NUCLEOSIDES; IN-VITRO; ANALOGS; TYPE-1; FUNCTIONALIZATION; OLIGONUCLEOTIDES;
D O I：
10.1016/j.ejmech.2013.02.042
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of 4'-[1,2,3]triazole-2'-deoxy-2'-fluoro-beta-D-arabinofuranosylcytosines (9-17) were prepared by Cu(I)-mediated [3 + 2] cycloaddition reactions (CuAAC) of 1-(4'-azido-2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)cytosine (1) with appropriate alkynes in good yields. Their structures were fully established by H-1 NMR, C-13 NMR, HRMS, and elemental analysis. Most of these nucleoside analogs exhibited potent anti-HIV-1 activity with no cytotoxicity observed at the highest tested concentration up to 25 mu M. Among them, compounds 9, 10 and 13 exhibited extremely potent antiviral activity, thus had a great potential for further development as novel nucleoside reverse transcriptase inhibitors (NRTIs) for the treatment of HIV-1 infection. Besides, the anti-HBV activity of compounds 10, 11 and 17 had been investigated. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：739 / 745
页数：7
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