| 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
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| 2010-10-01 | |
| 发表期刊 | CHEMICAL PAPERS
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| 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 |
| DOI | 10.2478/s11696-010-0047-1 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000280919800019 |
| 引用统计 | |
| 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 |
| 推荐引用方式 GB/T 7714 | 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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