(E)-3-(3-methoxybenzylidene)-1-methylindolin-2-one | 1148119-19-0

• 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)-3-(3-methoxybenzylidene)-1-methylindolin-2-one
• 英文别名: (3E)-3-[(3-methoxyphenyl)methylidene]-1-methylindol-2-one
• CAS: 1148119-19-0
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: IYKZGLSAZSJNJJ-RVDMUPIBSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  402.4±44.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基吲哚酮 、 3-甲氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以66%的产率得到(E)-3-(3-methoxybenzylidene)-1-methylindolin-2-one
  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

• Room-Temperature Palladium-Catalyzed Intramolecular Oxidative Aminocarbonylation of Vinylic C(sp²)-H Bonds with Amines and CO
  作者：Xu-Heng Yang、Kai Li、Ren-Jie Song、Jin-Heng Li

  DOI：10.1002/ejoc.201301284

  日期：2014.1

  A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation strategy by employing an oxidative functionalization of a vinyl C(sp2)–H bond.

  提出了一种获得 3-亚甲基吲哚-2-酮的新的、温和的途径，该途径通过在室温下钯催化的烯烃与胺和 CO 的分子内氧化氨基羰基化进行。该方法代表了一种新的氨基羰基化策略，通过采用氧化功能化乙烯基 C(sp2)-H 键。
• 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.