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; Ma, LY; Wang, M; Yin, DS; Zhou, TT; Chen, AZ; Ma, Z; Bian, C; Wang, SZ; Yang, ZY |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2012 |
| 卷号 | 68期号:9页码:2172-2178 |
| 关键词 | Sinomenine C-H functionalization Selectivity (Diacetoxylodo)benzene Immunomodulating activity |
| 通讯作者 | Yang, ZY (reprint author), Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China.,yangzhenyu@sioc.ac.cn ; bingsun@sibs.ac.cn ; yaoz@sioc.ac.cn |
| 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 | Chemistry |
| 类目[WOS] | Chemistry, Organic |
| 关键词[WOS] | RHEUMATOID-ARTHRITIS ; OXIDATION ; ACTIVATION ; MECHANISM ; QUINONES |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000301309000014 |
| 版本 | 出版稿 |
| 源URL | [http://202.127.25.143/handle/331003/646]  |
| 专题 | 上海生化细胞研究所_上海生科院生化细胞研究所 |
| 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 | Lou, YT.,Ma, LY.,Wang, M.,Yin, DS.,Zhou, TT.,...&Yao, ZJ.(2012).Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives.TETRAHEDRON,68(9),2172-2178. |
| MLA | Lou, YT,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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