(Z)-6-hydroxy-2-(2-methoxybenzylidene)benzofuran-3(2H)-one | 1234351-86-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-6-hydroxy-2-(2-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 6-hydroxy-2-(2'-methoxybenzylidene)benzofuran-3(2H)-one；(Z)-2-(2-methoxybenzylidene)benzofuran-3 (2H)-one；2'-methoxy-6-hydroxyaurone；(2Z)-6-hydroxy-2-(2-methoxybenzylidene)-1-benzofuran-3(2H)-one；(2Z)-6-hydroxy-2-[(2-methoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 1234351-86-0
• 化学式: C₁₆H₁₂O₄
• mdl: MFCD04144687
• 分子量: 268.269
• InChiKey: AUTVGGJLTZQXAE-NVNXTCNLSA-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (Z)-6-hydroxy-2-(2-methoxybenzylidene)benzofuran-3(2H)-one 、 1-(2-氯乙基)哌啶盐酸盐 在 potassium carbonate 、 乙醇 、 乙酰氯 作用下， 以 丙酮 为溶剂， 生成 (Z)-2-(2-methoxybenzylidene)-6-(2-(piperidin-1-yl)ethoxy)benzofuran-3(2H)-one hydrochloride
  参考文献：
  名称：

  Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors

  摘要：

  Alzheimer's disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure of sulfuretin. Of those synthesized, compound 10d showed ca. 1700-fold and 6-fold higher AChE inhibitory activity than sulfuretin and galantamine, respectively. This compound also ameliorated scopolamine-induced memory deficit in mice when administered orally at the dose of 1 and 2 mg/kg. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.11.004
• 作为产物：
  描述：

  2-溴-2,4-二羟基苯乙酮 在 sodium acetate 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (Z)-6-hydroxy-2-(2-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Discovery of aurones bearing two amine functionalities as SHIP2 inhibitors with insulin-sensitizing effect in rat myotubes

  摘要：

  带有两个胺官能团的醛酮 12a 是一种微摩尔 SHIP2 抑制剂，具有增强大鼠肌管葡萄糖摄取的特性。12a 在 Caco-2 细胞单层中表现出良好的渗透性，这表明它具有作为口服胰岛素增敏剂的潜力。

  DOI：

  10.1039/d3md00360d

文献信息

• Facile Synthesis of Dispiroheterocycles through One-Pot [3+2] Cycloaddition, and Their Antiviral Activity
  作者：Min Zhang、Wenbo Yang、Kailu Li、Ke Sun、Jianfen Ding、Liuqing Yang、Chunyin Zhu

  DOI：10.1055/s-0037-1611900

  日期：2019.10

  Abstract A facile synthesis of novel dispiroheterocycles has been developed through one-pot [3+2] cycloaddition between isatins, amino acids, and aurones. Thirty different dispiroheterocycles were synthesized eusing this method which features mild conditions, convenient operation, and high efficacy. Evaluation of the bioactivity of these dispiroheterocyclic products revealed antiviral activity against tobacco

  抽象的 通过在靛红，氨基酸和金黄色原子之间进行一锅[3 + 2]环加成反应，已经开发出新颖的双螺杂环化合物的简便合成方法。利用该方法，合成了三十种不同的双螺杂环化合物，其条件温和，操作方便，疗效高。对这些双螺杂环化合物的生物活性进行评估，发现其对烟草花叶病毒（TMV）具有抗病毒活性。 通过在靛红，氨基酸和金黄色原子之间进行一锅[3 + 2]环加成反应，已经开发出新颖的双螺杂环化合物的简便合成方法。利用该方法，合成了三十种不同的双螺杂环化合物，其条件温和，操作方便，疗效高。对这些双螺杂环化合物的生物活性进行评估，发现其对烟草花叶病毒（TMV）具有抗病毒活性。
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells
  作者：Seo Young Shin、Min Cheol Shin、Ji-Sun Shin、Kyung-Tae Lee、Yong Sup Lee

  DOI：10.1016/j.bmcl.2011.05.117

  日期：2011.8

  Sulfuretin is one of major constituents of Rhus verniciflua that exerts anti-inflammatory activities. Some of aurones were synthesized as sulfuretin derivatives and evaluated for their abilities to inhibit NO and PGE(2) production in LPS-induced RAW 264.7 cells in order to reveal the relationship. Of the aurones synthesized in the present study, 2h and 2i, which possess C-6 hydroxyl group in A-ring and methoxy substituents in B-ring, more potently inhibited NO and PGE(2) production and were less cytotoxic than sulfuretin. (C) 2011 Elsevier Ltd. All rights reserved.
• KR2016/142676
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis, and repurposing of O-aminoalkyl-sulfuretin analogs towards discovery of potential lead compounds as antileishmanial agents
  作者：Ahmed H.E. Hassan、Trong-Nhat Phan、Suyeon Moon、Chae Hyeon Lee、Yeon Ju Kim、Soo Bin Cho、Selwan M. El-Sayed、Yeonwoo Choi、Joo Hwan No、Yong Sup Lee

  DOI：10.1016/j.ejmech.2023.115256

  日期：2023.5