(Z)-3-(4-fluorobenzylidene)indolin-2-one | 90828-17-4

• 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-(4-fluorobenzylidene)indolin-2-one
• 英文别名: 3-(4-Fluorobenzylidene)indolin-2-one；(3Z)-3-[(4-fluorophenyl)methylidene]-1H-indol-2-one
• CAS: 90828-17-4
• 化学式: C₁₅H₁₀FNO
• 分子量: 239.249
• InChiKey: QIERHADIMMFZNE-LCYFTJDESA-N

物化性质

• 沸点：
  435.3±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-3-(4-fluorobenzylidene)indolin-2-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.31h， 以66%的产率得到(Z)-3-(4-fluorobenzylidene)indolin-2-one
  参考文献：
  名称：

  E–Z isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor

  摘要：

  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。

  DOI：

  10.1039/d0ra05288d

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。
• Oxindole Derivatives: Synthesis and Antiglycation Activity
  作者：Khalid Khan、Momin Khan、Nida Ambreen、Muhammad Taha、Fazal Rahim、Saima Rasheed、Sumayya Saied、Humaira Shafi、Shahnaz Perveen、Muhammad Choudhary

  DOI：10.2174/1573406411309050007

  日期：2013.6.1

  Oxindole derivatives 3-25 have been synthesized from commercially available oxindole by refluxing with different aromatic aldehydes in good yields. Their in vitro antiglycation potential has been evaluated. They showed a varying degree of antiglycation activity with IC50 values ranging between 150.4 - 856.7 µM. 3-[(3-Chlorophenyl)methylidene]- 1,3-dihydro-2H-indol-2-one (IC50 = 150.4 ± 2.5 µM) is the most active compound among the series, better than the standard rutin with an IC50 value 294.5 ± 1.50 µM. The structures of the compounds were elucidated by 1H-NMR and mass spectroscopy and elemental analysis. A limited structure-activity relationship has been developed.

  氧杂吲哚衍生物3-25是通过与不同的芳香醛在回流条件下反应，从市售的氧杂吲哚合成的，产率较高。它们的体外抗糖化潜力已被评估，显示出不同程度的抗糖化活性，其IC50值范围在150.4 - 856.7 µM之间。3-[(3-氯苯基)亚甲基]-1,3-二氢-2H-吲哚-2-酮（IC50 = 150.4 ± 2.5 µM）是该系列中活性最强的化合物，优于标准的芦丁，其IC50值为294.5 ± 1.50 µM。通过1H-NMR、质谱和元素分析对这些化合物的结构进行了阐明，并建立了有限的结构-活性关系。
• (Z)- and (E)-Arylidene-1,3-dihydroindol-2-ones: configuration, conformation, and infrared carbonyl stretching frequencies
  作者：Andreina Corsico Coda、Anna Gamba Invernizzi、Pier Paolo Righetti、Gianfranco Tacconi、Giuseppina Gatti

  DOI：10.1039/p29840000615

  日期：——

  The configuration and conformation of both (Z)- and (E)-arylidene-1,3-dihydroindol-2-ones were investigated. In the solid state the Z-isomer is planar whereas the E-isomer has the aryl group significantly twisted, as shown by two X-ray structures. A linear correlation was found between (co) and the σp+ of the substituents and this allows the conformation in solution and the degree of conjugation of

  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。
• METHOD OF USING AN INDOLINONE MOLECULE AND DERIVATIVES FOR INHIBITING LIVER FIBROSIS AND HEPATITIS
  申请人：Acclaim BioMed USA LLC

  公开号：US20150045395A1

  公开（公告）日：2015-02-12

  This invention relates to methods of reversing and inhibiting liver fibrosis and hepatitis using a small indolinone molecule Hesperadin and related compounds. Methods of identifying such agents and using them to inhibit the expression of collagens and ECM proteins including MMPs and TIMPs in purified hepatic stellate cells are provided. In vivo data of Hesperadin in inhibiting induced collagen production are presented. This method of specifically targeting drugs to hepatic stellate cells in vivo, provides a novel therapy for liver diseases.

  本发明涉及使用小分子indolinone Hesperadin及其相关化合物来逆转和抑制肝纤维化和肝炎的方法。提供了识别这些药物并将它们用于抑制纯化肝星状细胞中胶原和ECM蛋白质表达（包括MMPs和TIMPs）的方法。介绍了Hesperadin在抑制诱导的胶原产生方面的体内数据。这种特异性靶向药物作用于肝星状细胞的方法，为治疗肝病提供了一种新的疗法。
• Combined Scaffold Evaluation and Systems‐Level Transcriptome‐Based Analysis for Accelerated Lead Optimization Reveals Ribosomal Targeting Spirooxindole Cyclopropanes
  作者：Kevin X. Rodriguez、Erin N. Howe、Emily P. Bacher、Miranda Burnette、Jennifer L. Meloche、Jayda Meisel、Patricia Schnepp、Xuejuan Tan、Mayland Chang、Jeremiah Zartman、Siyuan Zhang、Brandon L. Ashfeld

  DOI：10.1002/cmdc.201900266

  日期：2019.9.18

  paramount. In this study, we combined scaffold-directed synthesis with a hybrid experimental and transcriptome analysis to identify bis-spirooxindole cyclopropanes that inhibit cancer cell proliferation through disruption of ribosomal function. These findings demonstrate the value of an integrated, biologically inspired synthesis and assay strategy for the accelerated identification of first-in-class

  随着进化的耐药性影响治疗疾病的努力，对表现出新的分子作用机制的小分子的需求至关重要。在这项研究中，我们将支架导向的合成与混合实验和转录组分析相结合，以鉴定可通过破坏核糖体功能抑制癌细胞增殖的双螺氧并吲哚环丙烷。这些发现证明了一种综合的，生物学启发的合成和分析策略对于加速识别一流癌症治疗候选物的价值。