(E)-3-(2,5-dimethoxybenzylidene)indolin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(2,5-dimethoxybenzylidene)indolin-2-one
• 英文别名: (E)-3-(2,5-dimethoxy-benzylidene)-1,3-dihydro-indol-2-one；(3E)-3-[(2,5-dimethoxyphenyl)methylidene]-1H-indol-2-one
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: DKGBVFRNIOJEKA-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,5-dimethoxybenzylidene)indolin-2-one 、 苯甲酰腈 在 potassium carbonate 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以63%的产率得到(Z)-2-(2,5-dimethoxyphenyl)-2-(2-oxoindolin-3-ylidene)acetonitrile
  参考文献：
  名称：

  Synthesis of 2-(2-oxoindolin-3-ylidene)-2-arylacetonitriles through transition metal-free C(sp2) CN bond construction

  摘要：

  DOI：

  10.1016/j.tet.2018.01.050
• 作为产物：
  描述：

  2-吲哚酮 、 2,5-二甲氧基苯甲醛 在 N-甲基-D-葡胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以91%的产率得到(E)-3-(2,5-dimethoxybenzylidene)indolin-2-one
  参考文献：
  名称：

  可生物降解的氨基糖“葡甲胺”催化高效合成重要的药用亚苄基-吲哚-2-酮衍生物

  摘要：

  已开发了以葡甲胺为绿色催化剂并以乙醇：水为反应介质在78°C高效合成生物学上重要的亚苄基-吲哚-2-酮衍生物的方法。研究了反应条件如溶剂，温度和催化剂用量的影响。本方法具有许多优点，例如操作简单，完成反应所需的时间更少，产物的收率高以及反应曲线干净。

  DOI：

  10.2174/1570178615666181030095728

文献信息

• [EN] NOVEL THERAPEUTIC USE OF INDOLINONE DERIVATIVES<br/>[FR] NOUVELLE UTILISATION THERAPEUTIQUE DE DERIVES D'INDOLINONE
  申请人：LEO PHARMA AS

  公开号：WO2005058309A1

  公开（公告）日：2005-06-30

  Certain oxindole compounds have been found to be effective in experimentally induced autoimmune encephalitis and are therefore suggested for the preparation of a medicament for the prevention, treatment or amelioration of multiple sclerosis, or to delay the onset of or reduce the relapse rate in multiple sclerosis.

  某些氧吲哚化合物已被发现在实验诱导的自身免疫性脑炎中具有有效性，因此建议用于制备用于预防、治疗或改善多发性硬化症的药物，或延缓多发性硬化症的发作或减少复发率。
• CeCl₃·7H₂O catalyzed C(sp²)−CN bond construction on water: Synthesis of (<i>Z</i>)-2-(2-Oxoindolin-3-ylidene)-2-arylacetonitriles
  作者：Yan Du、Zheng Li

  DOI：10.1080/00397911.2018.1540050

  日期：2019.1.2

  Abstract An environmentally friendly method for the construction of C(sp2)-CN bond on water has been described, and (Z)-2-(2-oxoindolin-3-ylidene)-2-arylacetonitriles were synthesized by using CeCl3· 7H2O as a catalyst. The reaction offers access to alkenyl nitriles in good-to-excellent yield. The investigations will be beneficial to reduce the use of toxic organic solvents and explore the efficient

  摘要 描述了一种在水中构建 C(sp2)-CN 键的环保方法，以 CeCl3·7H2O 为原料合成了 (Z)-2-(2-oxoindolin-3-ylidene)-2-芳基乙腈。一种催化剂。该反应提供了以良好到极好的收率获得烯基腈的途径。这些研究将有利于减少有毒有机溶剂的使用，探索有效的水催化过程。图形概要
• Novel therapeutic use
  申请人：Bouerat Duvold Maud Elysa Laetitia

  公开号：US20070167488A1

  公开（公告）日：2007-07-19

  Certain oxindole compounds have been found to be effective in experimentally induced autoimmune encephalitis and are therefore suggested for the preparation of a medicament for the prevention, treatment or amelioration of multiple sclerosis, or to delay the onset of or reduce the relapse rate in multiple sclerosis.

  某些恶唑酮化合物已被发现在实验性自身免疫脑炎中具有疗效，因此建议用于制备用于预防、治疗或改善多发性硬化症的药物，或者延迟多发性硬化症的发作或减少复发率。
• Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity
  作者：Wei Zhang、Mei-Lin Go

  DOI：10.1016/j.bmc.2008.12.052

  日期：2009.3

  Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventive potential. To investigate this possibility, we have synthesized and evaluated a series of functionalized 3-benzylidene-indolin-2-ones for induction of NQO1 in murine Hepa1c1c7 cells as well as antiproliferative activity against two human cancer cell lines (MCF-7, HCT116). The benzylideneindolinones were found to be good inducers of NQO1 activity, with 85% of test compounds able to increase basal NQO1 activity by more than twofold at concentrations of <= 10 mu M. By contrast, fewer compounds (11%) tested at the same concentration were able to reduce cell viability by more than 50%. Structure activity relationships showed that the nitrogen linked Michael acceptor moiety was an essential requirement for both activities. This common feature notwithstanding, substitution of the 3-benzylidene-indolin-2-one core structure affected NQO1 induction and antiproliferative activities in dissimilar ways, underscoring different structural requirements for these two activities. Nonetheless, promising compounds ( 10, 42, 45-48) were identified that combine selective induction of NQO1 with potent antiproliferative activity. A potential advantage of such agents would be the ability to provide added protection to normal cells by the up-regulation of NQO1 and other phase II enzymes while simultaneously targeting neoplastic cells. (C) 2008 Elsevier Ltd. All rights reserved.
• Indolin-2-ones with High in Vivo Efficacy in a Model for Multiple Sclerosis
  作者：Laëtitia Bouérat、Jef Fensholdt、Xifu Liang、Sophie Havez、Simon F. Nielsen、Jens R. Hansen、Simon Bolvig、Christina Andersson

  DOI：10.1021/jm0504151

  日期：2005.8.1

  The known KDR inhibitor SU5416 and several analogues of the indolin-2-one family were surprisingly found to be highly efficacious in the EAE model, an established model for multiple sclerosis. The high in vivo effect could be correlated to in vitro inhibition of the pro-inflammatory cytokine IL-2. Activity following po administration was obtained with several analogues and via the use of prodrugs.