(Z)-3-(2-hydroxybenzylidene)indolin-2-one | 40526-71-4

• 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: (Z)-3-(2-hydroxybenzylidene)indolin-2-one
• 英文别名: 3-(2-hydroxy-benzylidene)-1,3-dihydro-indol-2-one；3-salicylidene-indolin-2-one；3-Salicyliden-indolin-2-on；3-(2-Hydroxybenzylidene)indoline-2-one；(3Z)-3-[(2-hydroxyphenyl)methylidene]-1H-indol-2-one
• CAS: 40526-71-4
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: QJJAFCLEWYTXRC-XFXZXTDPSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  492.7±45.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

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 52.0h， 生成 (Z)-3-(2-hydroxybenzylidene)indolin-2-one
  参考文献：
  名称：

  Synthesis and anti-tyrosine kinase activity of 3-(substituted-benzylidene)-1, 3-dihydro-indolin derivatives: investigation of their role against p60c-Src receptor tyrosine kinase with the application of receptor docking studies

  摘要：

  A series of 3-(substituted-benzylidene)-1, 3-dihydro-indolin-2-thione derivatives were synthesized as modified congeners of 3-(substituted-benzylidene)-1, 3-dihydro-indolin-2-one series. All the synthesized compounds were examined for their in vitro anti-tyrosine kinase activity against p60c-Src. The activity results revealed that compounds (Z)-3-(4'-Dimethylamino-benzylidene)-1, 3-dihydro-indolin-2-thione (12) (E)-3-(2', 6'-Dichloro-benzylidene)-1, 3-dihydro-indolin-2-thione (13) and (E)-3-(3'-Hydroxy-4'-methoxy-benzylidene)-1, 3-dihydro-indolin-2-thione (19) exhibited anti-tyrosine kinase activity with IC50 value of 21.91, 21.20 and 30.92 microM, respectively. These results are comparable to PP1 [1-tert-Butyl-3-p-tolyl-1H-pyrazolo[3, 4-d]pyrimidine-4-yl-amine] (IC50=0.17 microM), which is reported as a potent and selective p60c-Src tyrosine kinase inhibitor. Some thio congeners are found to be more potent than oxo derivatives; however, no significant correlation was observed between the activity profiles of these two series. Docking program was used to investigate the docking mode of each compound at the active site. Among all of the compounds, only (Z)-3-(2'-Chloro-benzylidene)-1, 3-dihydro-indolin-2-one (8) and (E)-3-(3'-Nitro-benzylidene)-1, 3-dihydro-indolin-2-thione (16) were docked at the active site where the PP1 was embedded.

  DOI：

  10.1016/j.farmac.2005.01.015

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。
• Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
  作者：Md. Nurnobi Rashed、Abeda Sultana Touchy、Chandan Chaudhari、Jaewan Jeon、S.M.A. Hakim Siddiki、Takashi Toyao、Ken-ichi Shimizu

  DOI：10.1016/s1872-2067(19)63515-1

  日期：2020.6

  reusable catalyst for the C3-selective alkenylation of oxindole with aldehydes under solvent-free conditions. This catalytic method is generally applicable to different aromatic and aliphatic aldehydes, giving 3-alkyledene-oxindoles in high yields (87%–99%) and high stereoselectivities (79%–93% to E-isomers). This is the first example of the catalytic synthesis of 3-alkenyl-oxindoles from oxindole and

  摘要 我们在本文中报道，市售的 CeO2 是一种活性且可重复使用的催化剂，可用于在无溶剂条件下将 oxindole 与醛进行 C3 选择性烯基化。这种催化方法通常适用于不同的芳香族和脂肪族醛，以高产率（87%–99%）和高立体选择性（79%–93% 的 E-异构体）得到 3-亚烷基-羟吲哚。这是从羟吲哚和各种脂肪醛催化合成 3-烯基-羟吲哚的第一个例子。通过原位 IR 研究了 CeO2 上的路易斯酸位点与苯甲醛之间的路易斯酸碱相互作用。使用不同尺寸的 CeO2 催化剂的构效关系研究表明，无缺陷的 CeO2 表面是该反应的活性位点。
• 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。
• Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
  作者：Wang Delong、Wang Lanying、Wu Yongling、Song Shuang、Feng Juntao、Zhang Xing

  DOI：10.1016/j.ejmech.2017.02.050

  日期：2017.4

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.
• Wahl; Bagard, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909, vol. 149, p. 133
  作者：Wahl、Bagard

  DOI：——

  日期：——