Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives
文献类型：期刊论文
| 作者 | 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) |
| 刊名 | Tetrahedron
 |
| 出版日期 | 2012 |
| 卷号 | 68期号:9页码:2172-2178 |
| ISSN号 | 0040-4020 |
| 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 |
| 通讯作者 | 杨震宇 ; 孙兵 ; 姚祝军 |
| 英文摘要 | 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. |
| 学科主题 | 生命有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1016/j.tet.2012.01.009 |
| 语种 | 英语 |
| WOS记录号 | WOS:000301309000014 |
| 公开日期 | 2013-08-23 |
| 源URL | [http://202.127.28.38/handle/331003/28539]  |
| 专题 | 上海有机化学研究所_生命有机化学国家重点实验室 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：上海有机化学研究所
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