(Z)-6-hydroxy-2-(3-methoxybenzylidene)benzofuran-3(2H)-one

• 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-(3-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: (2Z)-6-hydroxy-2-(3-methoxybenzylidene)-1-benzofuran-3(2H)-one；(2Z)-6-hydroxy-2-[(3-methoxyphenyl)methylidene]-1-benzofuran-3-one
• 化学式: C₁₆H₁₂O₄
• mdl: MFCD04146777
• 分子量: 268.269
• InChiKey: XWRCMPMRAXNWBC-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

反应信息

• 作为反应物：
  描述：

  (Z)-6-hydroxy-2-(3-methoxybenzylidene)benzofuran-3(2H)-one 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 12.0h， 生成 (Z)‑2‑(3‑methoxybenzylidene)‑6‑((1‑(2‑(pyrrolidin‑1‑yl)ethyl)‑1H‑1,2,3‑triazol‑4‑yl)methoxy)benzofuran‑3(2H)‑one
  参考文献：
  名称：

  一些新型吡咯烷-三唑-橙酮杂化物抗消化酶的设计、合成、分子对接和生物学研究

  摘要：

  在这项工作中，我们成功设计并合成了一些新型吡咯烷-三唑-橙酮杂化物的文库，即 ( Z )-2-亚苄基-6-((1-(2-(吡咯烷-1-基)乙基)-1 H -1,2,3-三唑-4-基)甲氧基)苯并呋喃-3(2H ) -酮衍生物5(ak)。所有合成的杂化橙酮的结构均根据光谱（FT-IR、1 H NMR、13 C NMR）和 HRMS 数据得到确认。在生物学研究中，分析了合成化合物对消化酶、淀粉酶、脂肪酶和胰蛋白酶的影响。这些化合物对这些酶表现出不同的影响，因为胰蛋白酶和淀粉酶都被激活，但对脂肪酶具有显着的抑制作用。在检查合成化合物与酶的结合能时，观察到实验结果与对接结果部分一致。这些杂种橙酮对抗消化酶的体外和计算机结果表明它们作为抗炎和抗肥胖剂的潜力。

  DOI：

  10.1007/s11164-023-05221-1
• 作为产物：
  描述：

  6-羟基-2H-苯并呋喃-3-酮 、 3-甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到(Z)-6-hydroxy-2-(3-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones

  摘要：

  研究了生物碱金雀花碱对6-羟基和6-羟基-7-甲基香豆酮进行氨基甲基化的反应。结果表明，6-羟基香豆酮的氨基甲基化发生在苯并呋喃环的7位上，如果7位已被占据，则发生在5位上。

  DOI：

  10.1007/s10600-017-2096-y

文献信息

• Benzofuranone derivatives and a method for producing them
  申请人：Snow Brand Milk Products Co., Ltd.

  公开号：US06143779A1

  公开（公告）日：2000-11-07

  The present invention provides new benzofuranone derivatives and a method for producing the derivatives useful for a therapeutic agent for preventing and/or treating hormone dependent diseases. The present invention is a new benzofuranone derivative represented by a particular general formula (I). ##STR1## In the production, a particular benzofuranone compound and a particular benzaldehyde are reacted.

  本发明提供了新的苯并呋喃酮衍生物以及用于生产这些衍生物的方法，该方法对于预防和/或治疗激素依赖性疾病的治疗剂非常有用。本发明是由特定通式（I）表示的新苯并呋喃酮衍生物。在生产过程中，特定的苯并呋喃酮化合物和特定的苯甲醛进行反应。
• Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones
  作者：A. V. Popova、S. P. Bondarenko、E. V. Podobii、M. S. Frasinyuk、V. I. Vinogradova

  DOI：10.1007/s10600-017-2096-y

  日期：2017.7

  Aminomethylation of 6-hydroxy- and 6-hydroxy-7-methylaurones by the alkaloid cytisine was studied. It was shown that the aminomethylation of the 6-hydroxyaurones occurred at the 7-position of the benzofuran ring and at the 5-position if the 7-position was occupied.

  研究了生物碱金雀花碱对6-羟基和6-羟基-7-甲基香豆酮进行氨基甲基化的反应。结果表明，6-羟基香豆酮的氨基甲基化发生在苯并呋喃环的7位上，如果7位已被占据，则发生在5位上。
• Structure-Based Virtual Screening and De Novo Design of PIM1 Inhibitors with Anticancer Activity from Natural Products
  作者：Hwangseo Park、Jinwon Jeon、Kewon Kim、Soyeon Choi、Sungwoo Hong

  DOI：10.3390/ph14030275

  日期：——

  potency by chemical modifications of the 2-benzylidenebenzofuran-3(2H)-one scaffold led to the discovery of several nanomolar inhibitors with antiproliferative activities against human breast cancer cell lines. Conclusions: these new PIM1 kinase inhibitors are anticipated to serve as a new starting point for the development of anticancer medicine.

  背景：由于细胞增殖的增强和细胞凋亡的抑制作用，莫洛尼氏鼠白血病（PIM）1激酶的前病毒插入位点已成为多种人类癌症的治疗靶标。方法：为了鉴定有效的PIM1激酶抑制剂，通过引入适当的脱水能项改善了蛋白质-配体结合自由能功能，对植物来源的天然产物进行了基于结构的虚拟筛选和从头设计。结果：作为后续酶抑制试验的结果，发现了四类PIM1激酶抑制剂，其生化潜能范围从低微摩尔水平到亚微摩尔水平。大量对接模拟的结果表明，抑制活性源于多个氢键的形成以及ATP结合位点的疏水相互作用。通过化学修饰2-亚苄基苯并呋喃3（2）来优化生化效能H）-一个支架导致发现了几种对人乳腺癌细胞系具有抗增殖活性的纳摩尔抑制剂。结论：这些新的PIM1激酶抑制剂有望成为抗癌药物开发的新起点。
• 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.