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Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives
其他题名青藤碱C10位β-H区域及立体选择性官能团化: 一个获取更强效免疫调节衍生物的途径
Lou YT(楼杨通); Ma LY(马利燕); Wang M(王蒙); Yin DS(尹东升); Zhou TT(周婷婷); Chen AZ(陈爱中); Ma Z(马钊); Bian C(边超); Wang SZ(王少仲); Yang ZY(杨震宇); Sun B(孙兵); Yao ZJ(姚祝军)
2012
发表期刊Tetrahedron
ISSN0040-4020
卷号68期号:9页码:2172-2178
摘要Regio- and stereoselective C-10 beta-H functionalization of sinomenine, an economically available natural immunomodulating alkaloid, has been studied, developed and successfully applied to the synthesis of new immunosuppressive sinomenine derivatives in a protecting-free fashion. Regioselective oxidation of sinomenine with (diacetoxylodo)benzene (DIB) in water provided a single stable benzoquinone derivative 4, and subsequent 1,6-conjugated addition of 4 with alcohols, amines, and thiols afforded a new series of C-10 beta-H functionalized sinomenine derivatives stereoselectively. Some derivatives with a newly introduced 10 beta-bezenesulfanyl substituent exhibited much higher TNF-alpha inhibitory potency than their natural parent sinomenine. This work opens a convenient access to novel sinomenine derivatives with medicinal interests. (C) 2012 Elsevier Ltd. All rights reserved.
学科领域生命有机化学
部门归属中科院上海有机化学研究所; 中科院上海生命科学研究院; 南京大学
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收录类别SCI
语种英语
WOS记录号WOS:000301309000014
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被引频次:3[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28539
专题生命有机化学国家重点实验室
通讯作者Yang ZY(杨震宇); Sun B(孙兵); Yao ZJ(姚祝军)
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GB/T 7714
Lou YT,Ma LY,Wang M,et al. Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives[J]. Tetrahedron,2012,68(9):2172-2178.
APA 楼杨通.,马利燕.,王蒙.,尹东升.,周婷婷.,...&姚祝军.(2012).Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives.Tetrahedron,68(9),2172-2178.
MLA 楼杨通,et al."Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives".Tetrahedron 68.9(2012):2172-2178.
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