Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives

	Regio- and stereoselective C-10 beta-H functionalization of sinomenine: an access to more potent immunomodulating derivatives
	Lou, YT; Ma, LY; Wang, M; Yin, DS; Zhou, TT; Chen, AZ; Ma, Z; Bian, C; Wang, SZ; Yang, ZY
刊名	TETRAHEDRON
	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
内容类型	期刊论文
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.