Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues
Chen, Gang1,2; Hao, Xiao-Jiang2,3,4; Sun, Qian-Yun3,4; Ding, Jian5
2010-10-01
发表期刊CHEMICAL PAPERS
卷号64期号:5页码:673-677
摘要A new synthesis method of 3-(nitromethylene)indolin-2-one analogues is described, using the Henry reaction of isatin and N-substituted isatins with nitromethane followed by dehydration of the nitroaldol adduct with mesyl chloride. The use of diethylamine (rather than DBU) as the base catalyst in a solvent-free Henry reaction gave the nitroaldol adduct in sufficient purity as to allow its direct dehydration to nitroalkene. Overall yields for this two-step synthesis are satisfactory (typically 50-77 % after chromatographic purification). 3-(Nitromethylene)indolin-2-one analogues are valued protective agents against H2O2-induced apoptosis using PC12 cells, and for their cytotoxicity against the A549 and P388 lung cancer cell lines. One compound, (E)-1-benzyl-3-(nitromethylene)indolin-2-one (VIII), exhibited potent activity in the latter assay.
关键词3-(Nitromethylene)Indolin-2-one Diethylamine Antitumor Neuroprotection Catalyst
学科领域Chemistry, Multidisciplinary
DOI10.2478/s11696-010-0047-1
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:000280919800019
引用统计
被引频次:8[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/14555
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Xian Shiyou Univ, Coll Chem & Chem Engn, Xian 710065, Shaanxi, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Yunnan, Peoples R China
3.Key Lab Chem Nat Prod Guizhou Prov, Guiyang 550002, Peoples R China
4.Chinese Acad Sci, Guiyang 550002, Peoples R China
5.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
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Chen, Gang,Hao, Xiao-Jiang,Sun, Qian-Yun,et al. Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues[J]. CHEMICAL PAPERS,2010,64(5):673-677.
APA Chen, Gang,Hao, Xiao-Jiang,Sun, Qian-Yun,&Ding, Jian.(2010).Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues.CHEMICAL PAPERS,64(5),673-677.
MLA Chen, Gang,et al."Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues".CHEMICAL PAPERS 64.5(2010):673-677.
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