(E)-4-((2-oxoindolin-3-ylidene)methyl)benzonitrile | 90828-15-2

• 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: (E)-4-((2-oxoindolin-3-ylidene)methyl)benzonitrile
• 英文别名: 4-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]benzonitrile
• CAS: 90828-15-2
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: PALSWWUKBADMJZ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-((2-oxoindolin-3-ylidene)methyl)benzonitrile 反应 0.08h， 以30%的产率得到4-[2-Oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-benzonitrile
  参考文献：
  名称：

  （Z）-和（E）-亚芳基-1,3-二氢吲哚-2-酮：构型，构型和红外羰基拉伸频率

  摘要：

  研究了（Z）-和（E）-亚芳基-1,3-二氢吲哚-2-酮的构型和构象。在固态下，Z-异构体是平面的，而E-异构体的芳基明显扭曲，如两个X射线结构所示。发现（c o）与取代基的σp +之间存在线性关系，这可以推断溶液中的构象以及Ar–C C–C O系统的共轭程度。

  DOI：

  10.1039/p29840000615
• 作为产物：
  描述：

  2-吲哚酮 、 4-氰基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以78%的产率得到(E)-4-((2-oxoindolin-3-ylidene)methyl)benzonitrile
  参考文献：
  名称：

  Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.12.052

文献信息

• <i>E</i>–<i>Z</i> isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor
  作者：Chada Raji Reddy、Veeramalla Ganesh、Ajay K. Singh

  DOI：10.1039/d0ra05288d

  日期：——

  (E)-3-Benzylidene-indolin-2-ones were efficiently converted to their corresponding (Z) -isomers at low temperature in the presence of light.

  在光的存在下，(E)-3-苄基吲哚-2-酮可以在低温下高效地转化为其相应的(Z)异构体。