3-(3-nitro-benzylidene)-1,3-dihydro-indol-2-one | 40811-73-2

• 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: 3-(3-nitro-benzylidene)-1,3-dihydro-indol-2-one
• 英文别名: 3-(3-nitro-benzylidene)-indolin-2-one；3-(3-Nitro-benzyliden)-indolin-2-on；(3Z)-3-[(3-Nitrophenyl)methylidene]-2,3-dihydro-1H-indol-2-one；(3Z)-3-[(3-nitrophenyl)methylidene]-1H-indol-2-one
• CAS: 40811-73-2
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: BZWZITZVOQYHCA-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 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：
  74.9
• 氢给体数：
  1
• 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 52.0h， 生成 3-(3-nitro-benzylidene)-1,3-dihydro-indol-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。
• 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。
• Wahl; Bagard, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1909, vol. 149, p. 133
  作者：Wahl、Bagard

  DOI：——

  日期：——
• Neber; Roecker, Chemische Berichte, 1923, vol. 56, p. 1712
  作者：Neber、Roecker

  DOI：——

  日期：——
• NOVEL THERAPEUTIC USE OF INDOLINONE DERIVATIVES
  申请人：LEO PHARMA A/S

  公开号：EP1696906A1

  公开（公告）日：2006-09-06