1-methyl-3-[(E)-2-(4-nitro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one | 56680-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-methyl-3-[(E)-2-(4-nitro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one
• 英文别名: (3E)-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethylidene]indol-2-one
• CAS: 56680-36-5
• 化学式: C₁₇H₁₂N₂O₄
• 分子量: 308.293
• InChiKey: UYUTWQKUYIOXGG-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3-[(E)-2-(4-nitro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以40%的产率得到1-Methyl-3-[2-(4-nitro-phenyl)-2-oxo-eth-(Z)-ylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  一种容易的路易斯酸介导的从（E）-到（Z）-羟吲哚-3-亚基酮的异构化反应。

  摘要：

  在室温下，CH 2 Cl 2中的AlCl 3可以很容易地将（E）-2-氧代吲哚-3-亚基酮异构化为（Z）异构体。（Z）-构型中作为二齿配体的不饱和二羰基骨架的行为可能是异构化的关键步骤。讨论了可以制备几种尚不知道的产物的反应极限。

  DOI：

  10.1016/s0040-4020(01)85706-9
• 作为产物：
  描述：

  1-甲基靛红 在 盐酸 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 1-methyl-3-[(E)-2-(4-nitro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

  摘要：

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.056

文献信息

• Phosphine-Catalyzed Asymmetric [4+2] Annulation of Vinyl Ketones with Oxindole-Derived α,β-Unsaturated Imines: Enantioselective Syntheses of 2′,3′-Dihydro-1′<i>H</i>-spiro[indoline-3,4′-pyridin]-2-ones
  作者：Xiao-Nan Zhang、Gen-Qiang Chen、Xiang Dong、Yin Wei、Min Shi

  DOI：10.1002/adsc.201300828

  日期：2013.11.25

  AbstractA novel asymmetric [4+2] annulation of vinyl ketones with oxindole‐derived α,β‐unsaturated imines has been developed in the presence of a multifunctional thiourea‐phosphine catalyst derived from a natural amino acid, providing the first phosphine‐catalyzed enantioselective synthesis of 2′,3′‐dihydro‐1′H‐spiro[indoline‐3,4′‐pyridin]‐2‐ones in good yields with excellent stereoselectivities under mild conditions.magnified image
• Heterodiene syntheses—XIV
  作者：G. Tacconi、P. Iadarola、F. Marinone、P.P. Righetti、G. Desimoni

  DOI：10.1016/0040-4020(75)85054-x

  日期：1975.1
• Giuseppe Faita, Mariella Mella, PierPaolo Righetti*, Gianfranco Tacconi, Tetrahedron, 50 (1994) N 37, S 10955-10962
  作者：Giuseppe Faita, Mariella Mella, PierPaolo Righetti*, Gianfranco Tacconi

  DOI：——

  日期：——