3-[(4-ethoxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one | 1464083-09-7

• 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-[(4-ethoxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-[(E)-(4-ethoxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one；(E)-3-(4-ethoxybenzylidene)indolin-2-one；(3E)-3-[(4-ethoxyphenyl)methylidene]-1H-indol-2-one
• CAS: 1464083-09-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: HRMBLFNBKLEZKA-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吲哚酮 、 4-乙氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以59 %的产率得到3-[(4-ethoxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  3-Arylidene-2-oxindoles 作为有效的 NRH:Quinone 氧化还原酶 2 抑制剂。

  摘要：

  NRH:quinone oxidoreductase 2 (NQO2) 酶在神经退行性疾病、疟疾、青光眼、COVID-19 和癌症等各种疾病的发病机制中起着重要作用。已知 NQO2 表达在一些癌细胞系中增加。由于 3-arylidene-2-oxindoles 广泛用于新型抗癌药物的设计，例如激酶抑制剂，因此研究此类结构是否对 NQO2 具有额外活性很有趣。在此，我们报告了 3-亚芳基-2-羟吲哚作为新型 NRH:quinone 氧化还原酶抑制剂的合成和研究。结果表明，在亚芳基部分具有 6 元芳基的羟吲哚主要以 E 异构体形式获得，而对于一些 5 元芳基，Z 异构体占优势。最活跃的化合物抑制 NQO2，IC50 为 0.368 µM。oxindoles 中双键的存在对 NQO2 抑制活性至关重要。合成化合物的 NQO2 抑制活性与其对 A549 细胞系的细胞毒性作用之间没有相关性。

  DOI：

  10.3390/molecules28031174

文献信息

• 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。
• 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.
• ANTI-GLYCATION PROPERTIES OF OXINDOLE DERIVATIVES
  申请人：Choudhary Muhammad Iqbal

  公开号：US20150038543A1

  公开（公告）日：2015-02-05

  This invention provides a series of new oxindole derivatives 1-21, evaluated for their antiglycation potential by using in vitro BSA-MG glycation model. These derivatives showed a varying degree of antiglycation activity with IC 50 values ranging between 150-856 μM. Compound 14 (IC 50 =150.4±2.5 μM) was found to be the most potent among all derivatives, even better than the standard inhibitor i.e. rutin (IC 50 =294.5±1.50 followed by compounds 13 and 8 with IC 50 value of 194.40±2.5 and 211.41±4.1 μM, respectively.