(2Z)-2-(2-chlorobenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one | 1234351-74-6

• 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: (2Z)-2-(2-chlorobenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one
• 英文别名: (2Z)-6-hydroxy-2-(2-chlorobenzylidene)-1-benzofuran-3(2H)-one；(Z)-2-(2-chlorobenzylidene)-6-hydroxybenzofuran-3(2H)-one；(Z)-6-hydroxy-2-(2-chlorobenzylidene)benzofuran-3(2H)-one；2-(2'-chlorobenzylidene)-6-hydroxybenzofuran-3(2H)-one；(2Z)-2-[(2-chlorophenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
• CAS: 1234351-74-6
• 化学式: C₁₅H₉ClO₃
• mdl: MFCD04065083
• 分子量: 272.688
• InChiKey: JRUSQMJYCWZQOD-AUWJEWJLSA-N

物化性质

• 沸点：
  498.9±45.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(2-chlorobenzylidene)-6-hydroxy-1-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‑(2‑chlorobenzylidene)‑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 、 2-氯苯甲醛 在 哌嗪 作用下， 以 乙醇 为溶剂， 生成 (2Z)-2-(2-chlorobenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  亚苄基苯并呋喃酮衍生物的合成作为检测细胞中淀粉样原纤维的探针

  摘要：

  聚集蛋白是多种神经退行性疾病的常见原因，如阿尔茨海默病（AD）、帕金森病等。事实证明，像淀粉样蛋白这样的蛋白质聚集...

  DOI：

  10.1080/07391102.2023.2184635

文献信息

• Carboxylated aurone derivatives as potent inhibitors of xanthine oxidase
  作者：Oksana V. Muzychka、Oleksandr L. Kobzar、Antonina V. Popova、Mykhaylo S. Frasinyuk、Andriy I. Vovk

  DOI：10.1016/j.bmc.2017.04.048

  日期：2017.7

  study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4′-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar

  黄嘌呤氧化酶是治疗高尿酸血症和痛风的潜在靶标。在这项研究中，合成了许多A环和B环羧化的金酮衍生物，并评估了它们在体外抑制黄嘌呤氧化酶的能力。根据获得的结果，观察到两个不同范围的抑制活性。发现在B环的4'-位具有羧酸基团的金黄色素是该酶的有效抑制剂，其IC 50值在低微摩尔范围内。这些化合物的作用比在6-位具有羧基甲氧基的A-环修饰的金酮的作用高约50倍。使用分子对接计算解释了黄嘌呤氧化酶活性位点中羧化金氧烷的结合方式。
• 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。
• 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.
• Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease
  作者：Tara Man Kadayat、Suhrid Banskota、Pallavi Gurung、Ganesh Bist、Til Bahadur Thapa Magar、Aarajana Shrestha、Jung-Ae Kim、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2017.06.018

  日期：2017.9

  To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1-Hinden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-alpha-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-alpha-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-kappa B transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-alpha gene, with compound 55 showing better efficacy. This inhibition of TNF-alpha expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-alpha expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, molecular docking and biological studies of some novel pyrrolidine-triazole-aurone hybrids against digestive enzymes
  作者：Sanjeev Kumar、Ekta Lathwal、Bhavna Saroha、Gourav Kumar、Arpana Bhardwaj、Poonam Bishnoi、Manishita Rani、Neera Raghav、Ramesh Kumar、Suresh Kumar

  DOI：10.1007/s11164-023-05221-1

  日期：2024.3

  effects on these enzymes as both trypsin and amylase were activated, but a significant inhibition was achieved for the lipase enzyme. Upon examining the binding energies of the synthesized compounds with the enzymes, it was observed that the experimental findings partially aligned with the docking results. These in vitro and in silico results of these hybrid aurones against digestive enzymes, signify their

  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。