Synthesis and Biological Evaluation of 7-Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone

被引：9
|
作者：
Schuenemann, Katrin [1 ,2 ]
Furkert, Daniel P. [1 ]
Connelly, Stephen [3 ]
Fraser, John D. [2 ]
Sperry, Jonathan [1 ]
Brimble, Margaret A. [1 ]
机构：
[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand
[2] Univ Auckland, Dept Mol Med & Pathol, Auckland 1, New Zealand
[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 01期
关键词：
Viruses; Oxa-Pictet-Spengler reaction; Quinones; Biological activity; Inhibitors; 3C-PROTEASE INHIBITOR; ENANTIOSELECTIVE SYNTHESIS; PRECURSOR PROTEINS; FORMAL SYNTHESIS; DEOXY ANALOGS; POLIOVIRUS; GENOME; BROMONAPHTHOQUINONES; STEREOCHEMISTRY; EFFICIENT;
D O I：
10.1002/ejoc.201301515
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of (+/-)-7-deoxythysanone and three analogues has been developed. The key oxa-Pictet-Spengler reaction enabled the synthesis of the naphthopyran precursor, which could be readily converted to 7-deoxythysanone and three related analogues. The biological activity of these compounds was also evaluated against HRV 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7-oxa functionality.
引用
收藏
页码：122 / 128
页数：7
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