Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydrofurochroman Scaffolds for Drug Discovery

doi:10.1002/ejoc.201600315

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	Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydrofurochroman Scaffolds for Drug Discovery
	Qiu, Lin 1; Wang, Dongwei 1; Lei, Yubing 1; Gao, Lixin 2; Liu, Shunying 1; Li, Jia2 ; Hu, Wenhao 1
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2016-05
期号	15 页码:2671-2680
关键词	Multicomponent reactions Cascade reactions Cyclization Drug discovery Polycycles Oxygen heterocycles
ISSN号	1434-193X
DOI	10.1002/ejoc.201600315
文献子类	Article
英文摘要	A one-pot synthesis of new oxindole-fused polycyclic scaffolds is reported. The process involves a three-component [3+2] cycloaddition followed by cyclization through an intramolecular Michael addition. The reaction gives easy access to oxindole-fused spirotetrahydrofurochromans in moderate to good yields with high regio- and diastereoselectivity. These compounds could be useful for for drug discovery. Further modification was achieved by reduction of the nitro group, and intramolecular amide formation to give the corresponding lactams. The resulting heterocyclic products show good inhibitory activity against the enzyme PTP1B in vitro.
资助项目	National Natural Science Foundation of China (NSFC)[21125209] ; National Natural Science Foundation of China (NSFC)[21332003] ; Ministry of Science and Technology (MOST) of China[2011CB808600] ; Science and Technology Commission of Shanghai Municipality (STCSM)[12JC1403800] ; Science and Technology Commission of Shanghai Municipality (STCSM)[15ZR1411000] ; Wuhan University of Technology (WUT)[2015-KF-11]
WOS关键词	ONE-POT SYNTHESIS ; CARBONYL YLIDES ; MULTICOMPONENT REACTIONS ; STEREOSELECTIVE-SYNTHESIS ; CYCLOADDITION REACTIONS ; DOMINO REACTION ; 1,3-DIPOLAR CYCLOADDITIONS ; EFFICIENT CONSTRUCTION ; DIPOLAR CYCLOADDITION ; 4-COMPONENT SYNTHESIS
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000377251800011
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276050]
专题	国家新药筛选中心中科院受体结构与功能重点实验室新药研究国家重点实验室药物安全性评价中心
通讯作者	Liu, Shunying; Hu, Wenhao
作者单位	1.E China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst MateriaMed, Natl Ctr Drug Screening, State Key Lab Drug Res, Shanghai, Peoples R China
推荐引用方式 GB/T 7714	Qiu, Lin,Wang, Dongwei,Lei, Yubing,et al. Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydrofurochroman Scaffolds for Drug Discovery[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2016(15):2671-2680.
APA	Qiu, Lin.,Wang, Dongwei.,Lei, Yubing.,Gao, Lixin.,Liu, Shunying.,...&Hu, Wenhao.(2016).Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydrofurochroman Scaffolds for Drug Discovery.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(15),2671-2680.
MLA	Qiu, Lin,et al."Diastereoselective Three-Component Cascade Reaction to Construct Oxindole-Fused Spirotetrahydrofurochroman Scaffolds for Drug Discovery".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .15(2016):2671-2680.