C5-Modified nucleosides exhibiting anticancer activity

被引:62
作者
Lee, Yoon-Suk [1 ]
Park, Sun Min [1 ]
Kim, Hwan Mook [2 ]
Park, Song-Kyu [2 ]
Lee, Kiho [2 ]
Lee, Chang Woo [2 ]
Kim, Byeang Hyean [1 ]
机构
[1] Pohang Univ Sci & Technol, Dept Chem, BK Sch Mol Sci, Pohang 790784, South Korea
[2] Bioevaluat Ctr, KRIBB, Taejon 305806, South Korea
关键词
Anticancer; Nucleoside; Triazole; Isoxazole; Cycloaddition; CANCER; IDENTIFICATION; CYTOTOXICITY; CLOFARABINE; ISOXAZOLE; ANALOGS; DESIGN; CELLS;
D O I
10.1016/j.bmcl.2009.06.072
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4688 / 4691
页数:4
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