(E)-3-(2-methoxybenzylidene)indolin-2-one | 50882-26-3

• 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-(2-methoxybenzylidene)indolin-2-one
• 英文别名: (3E)-3-[(2-methoxyphenyl)methylidene]-1H-indol-2-one
• CAS: 50882-26-3
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: NEQZEVOPIKSAJP-JLHYYAGUSA-N

物化性质

• 熔点：
  221-222 °C
• 沸点：
  469.4±45.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-methoxybenzylidene)indolin-2-one 以 氘代乙腈 为溶剂， 生成 3-(2-methoxybenzylidene)indolin-2-one
  参考文献：
  名称：

  高效羟吲哚基分子光电开关

  摘要：

  3-亚苄基-二氢吲哚-2-酮对于制药工业非常重要。这些化合物的生物学特性已被广泛报道，但几乎没有对其光化学活性进行研究。在这里，我们提出了 3-亚苄基-二氢吲哚-2-酮作为一类有前途的光开关，具有高产率、强大的光化学开关和高达 50% 的量子产率。

  DOI：

  10.1002/chem.202301634
• 作为产物：
  描述：

  2-吲哚酮 、 邻甲氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以71%的产率得到(E)-3-(2-methoxybenzylidene)indolin-2-one
  参考文献：
  名称：

  高效羟吲哚基分子光电开关

  摘要：

  3-亚苄基-二氢吲哚-2-酮对于制药工业非常重要。这些化合物的生物学特性已被广泛报道，但几乎没有对其光化学活性进行研究。在这里，我们提出了 3-亚苄基-二氢吲哚-2-酮作为一类有前途的光开关，具有高产率、强大的光化学开关和高达 50% 的量子产率。

  DOI：

  10.1002/chem.202301634

文献信息

• Synthesis of ( <i>E</i> )‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp ³ –H Bonds of Oxindoles and Benzylamines
  作者：Kovuru Gopalaiah、Ankit Tiwari

  DOI：10.1002/ejoc.202001300

  日期：2020.12.13

  An iron‐catalyzed direct access to (E)‐3‐alkylideneindolin‐2‐ones through oxidative condensation of oxindoles with benzylamines is described. The procedure utilizes molecular oxygen as a clean and terminal oxidant.

  描述了铁催化的氧吲哚与苄基胺的氧化缩合直接生成（E）-3-亚烷基亚吲哚啉-2-酮的方法。该程序利用分子氧作为清洁的终端氧化剂。
• 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。
• GIF-2209, an Oxindole Derivative, Accelerates Melanogenesis and Melanosome Secretion via the Modification of Lysosomes in B16F10 Mouse Melanoma Cells
  作者：Miyu Watanabe、Kyoka Kawaguchi、Yusuke Nakamura、Kyoji Furuta、Hiroshi Takemori

  DOI：10.3390/molecules27010177

  日期：——

  Melanogenesis and melanosome secretion are regulated by several mechanisms. In this study, we found that the oxindole derivative GIF-2209 accelerated melanogenesis associated with the discrimination in the expression and intracellular distributions of two melanogenic enzymes, tyrosinase (TYR) and tyrosinase-related protein-1 (TYRP-1). GIF-2209 upregulated the expression of TYR via a microphthalmia transcription factor (MITF)-independent mechanism, leading to high expression of protein. In contrast, GIF-2209 did not alter the mRNA levels of TYRP-1 and suppressed its protein levels. GIF-2209 induced the dissociation of TYR from TYRP-1 but did not alter the association between TYR and CD63, a melanosome and lysosome marker. The protein levels of CD63 were also upregulated by GIF-2209. GIF-2209 induced lysosome expansion and redistribution in all areas of the cytosol, accompanied by autophagy acceleration (upregulation of LC3BII protein levels and downregulation of p62 protein levels). In addition, GIF-2209 stimulated the secretion of melanosomes containing high levels of TYR, TYRP-1, and CD63 proteins. The GIF-2209 mediated melanosome secretion was sensitive to the lysosome inhibitor chloroquine. These results suggest that GIF-2209 may activate lysosomal functions with TYR gene expression, while it accelerates melanosome secretion, which finally leads to the depletion of intracellular melanogenic enzyme, especially TYRP-1 protein.

  黑色素生成和黑色体分泌受到几种机制的调节。在这项研究中，我们发现氧吲哚衍生物GIF-2209加速了与两种黑色生成酶酪氨酸酶（TYR）和酪氨酸酶相关蛋白-1（TYRP-1）的表达和细胞内分布有关的黑色素生成。GIF-2209通过一种与微小眼转录因子（MITF）无关的机制上调了TYR的表达，导致蛋白表达量增加。相反，GIF-2209没有改变TYRP-1的mRNA水平，并抑制了其蛋白水平。GIF-2209诱导了TYR与TYRP-1的解离，但没有改变TYR与CD63（黑色体和溶酶体标记物）之间的结合。CD63的蛋白水平也被GIF-2209上调。GIF-2209诱导了溶酶体在细胞质的所有区域的扩张和重新分布，并伴随着自噬的加速（LC3BII蛋白水平上调和p62蛋白水平下调）。此外，GIF-2209刺激了含有高水平TYR、TYRP-1和CD63蛋白的黑色体分泌。GIF-2209介导的黑色体分泌对溶酶体抑制剂氯喹敏感。这些结果表明，GIF-2209可能通过激活溶酶体功能与TYR基因表达相结合，同时加速黑色体分泌，最终导致细胞内黑色生成酶，特别是TYRP-1蛋白的耗竭。
• CeCl₃·7H₂O catalyzed C(sp²)−CN bond construction on water: Synthesis of (<i>Z</i>)-2-(2-Oxoindolin-3-ylidene)-2-arylacetonitriles
  作者：Yan Du、Zheng Li

  DOI：10.1080/00397911.2018.1540050

  日期：2019.1.2

  Abstract An environmentally friendly method for the construction of C(sp2)-CN bond on water has been described, and (Z)-2-(2-oxoindolin-3-ylidene)-2-arylacetonitriles were synthesized by using CeCl3· 7H2O as a catalyst. The reaction offers access to alkenyl nitriles in good-to-excellent yield. The investigations will be beneficial to reduce the use of toxic organic solvents and explore the efficient

  摘要 描述了一种在水中构建 C(sp2)-CN 键的环保方法，以 CeCl3·7H2O 为原料合成了 (Z)-2-(2-oxoindolin-3-ylidene)-2-芳基乙腈。一种催化剂。该反应提供了以良好到极好的收率获得烯基腈的途径。这些研究将有利于减少有毒有机溶剂的使用，探索有效的水催化过程。图形概要
• Synthesis of Spirocyclopropane Oxindoles via Michael-Initiated Cyclopropanation of Pyridinium Salts with 3-Ylidene Oxindoles
  作者：Hongjun Ren、Jun-Qi Zhang、Yujia Gao、Jinyu Song、Dandan Hu、Maozhong Miao

  DOI：10.1055/a-1327-6388

  日期：2021.4

  A Michael-initiated ring closure reaction of pyridinium salts with arylidene oxindoles has been developed. A wide range of aryl substituted spriocyclopropane oxindoles have been achieved in moderate to good yields (41–99%). This efficient strategy exhibits good functional group compatibility and may serve as an attractive method for the synthesis of diverse cyclopropanes.

  已经开发了吡啶盐与亚芳基羟吲哚的迈克尔引发的闭环反应。已经以中等至良好的产率 (41-99%) 获得了范围广泛的芳基取代的螺环丙烷羟吲哚。这种有效的策略表现出良好的官能团兼容性，可以作为合成各种环丙烷的有吸引力的方法。