(E)-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one
• 英文别名: (E)-3-(3-hydroxy-4-methoxy-benzylidene)-1,3-dihydro-indol-2-one；(3E)-3-[(3-hydroxy-4-methoxyphenyl)methylidene]-1H-indol-2-one
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: BQINENDEUIXMAZ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 在 哌啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (E)-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-(Substituted-benzylidene)-1,3-dihydro-indolin Derivatives as Human Protein Kinase CK2 and p60c-Src Tyrosine Kinase Inhibitors

  摘要：

  人类蛋白激酶 CK2 是一种无处不在的丝氨酸/苏氨酸激酶，通常存在于由两个催化亚基（α 和/或 α′）和两个调节亚基 β 组成的四聚体复合物中。尽管越来越多的证据表明，CK2 除了参与一系列复杂的细胞功能外，还参与细胞活力、细胞增殖和肿瘤转化。本研究测试了一系列 3-（取代-亚苄基）-1,3-二氢-吲哚啉-2-硫酮衍生物和相应的吲哚啉-2-酮同系物在体外对人类重组蛋白激酶 CK2 的抑制作用。将这些化合物的功效与它们对 p60c-Src 酪氨酸激酶的抑制结果进行了比较。结果发现，在抑制 CK2 和 p60c-Src 酪氨酸激酶方面，3-（取代-亚苄基）-1,3-二氢-吲哚啉-2-硫酮衍生物比吲哚啉-2-酮同系物更有效。

  DOI：

  10.1248/bpb.30.715

文献信息

• 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.