2-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one
• 英文别名: 2-(4-bromophenyl)-7-hydroxychromen-4-one
• 化学式: C₁₅H₉BrO₃
• 分子量: 317.139
• InChiKey: YPLFRIQYJICETL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (Z)-N'-((2-(4-bromophenyl)-7-hydroxy-4-oxo-4H-chromen-8-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

  摘要：

  A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC₅₀ = 1.343 µM) and L12 (IC₅₀ = 1.207 µM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.

  DOI：

  10.1016/j.bioorg.2020.104370
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 碘 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.67h， 生成 2-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Discovery of flavone-derivatives as the new skeleton of transient receptor potential vanilloid 3 channel antagonists

  摘要：

  DOI：

  10.1016/j.bmcl.2023.129577

文献信息

• Synthesis of oxygen heterocycles
  作者：A.K. Ganguly、P.K. Mahata、D. Biswas

  DOI：10.1016/j.tetlet.2005.12.062

  日期：2006.2

  A generalised scheme for the synthesis of flavones, flavonones and chromones involving 3-acyl-γ-pyrone intermediates has been developed. Convenient synthesis of other oxygen heterocycles using similar procedure have been outlined.

  已经开发出一种合成3-酮-γ-吡喃酮中间体的黄酮，黄酮和色酮的通用方案。已经概述了使用类似方法方便地合成其他氧杂环的方法。
• Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids
  作者：Venkata Swamy Tangeti、D. Vasundhara、K.V.V.V. Satyanarayana、Kaja Srinivas Pavan Kumar

  DOI：10.14233/ajchem.2017.20550

  日期：——

  A new series of dihydro-1H-furo[2,3-c]pyrazole-flavone hybrids were synthesized from one-pot four-component reaction of b-keto ester (1), hydrazine (2), 7-hydroxy 8-formyl flavones (3), pyridiniumylide (4) in presence of NEt3 as catalyst under ethanol reflux conditions and their antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, furo[2,3-c]pyrazole-flavone with C4-methoxy substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, (4S,5S)-ethyl 4-(7-hydroxy-5-methoxy-4-oxo-2-(2,4,6-trimethoxyphenyl)-4H-chromen-8-yl)-3-methyl-4,5-dihydro-1H-furo[2,3-c]pyrazole-5-carboxylate (8r) showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the dihydro-1H-furo[2,3-c]pyrazole-flavones are specifically target the cancer cell lines.

  一系列二氢-1H-呋喃[2,3-c]吡唑-黄酮杂合物通过一锅四组分反应合成，反应物包括β-酮酯（1）、肼（2）、7-羟基-8-醛黄酮（3）和吡啶亚胺（4），在三乙胺（NEt3）催化下于乙醇回流条件下进行。随后评估了这些化合物对人类癌细胞系的抗增殖活性，包括喉癌（Hep2）、肺腺癌（A549）和宫颈癌（HeLa）。在这些化合物中，C4-取代的甲氧基二氢-1H-呋喃[2,3-c]吡唑-黄酮被选为进一步结构-活性关系（SAR）研究的对象。在这些衍生物中，(4S,5S)-乙基4-(7-羟基-5-甲氧基-4-氧基-2-(2,4,6-三甲氧基苯基)-4H-香豆烯-8-基)-3-甲基-4,5-二氢-1H-呋喃[2,3-c]吡唑-5-羧酸酯（8r）对所有三种癌细胞系表现出最强的细胞毒活性。毒性研究表明，二氢-1H-呋喃[2,3-c]吡唑-黄酮特别靶向癌细胞系。
• Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor
  作者：Mahdiyeh H. S. Javadi、Aida Iraji、Maliheh Safavi、Hamed Montazeri、Parastoo Tarighi、Samane Eftekhari、Latifeh Navidpour、Seyedeh Sara Mirfazli

  DOI：10.1007/s00044-021-02767-w

  日期：2021.9

  optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound

  近年来，专注于具有选择性活性的新型强效抗癌药物是癌症治疗的最大挑战之一。乳腺癌是最常见的癌症，也是女性癌症死亡的主要原因。硫酸酯酶在将硫酸化类固醇转化为非硫酸化类固醇激素方面发挥着重要作用，这会增加许多激素依赖性癌症（如乳腺癌）的生长和发展。在这方面，进行了基于结构的优化以设计新的黄酮磺酸盐药效团作为新的类固醇硫酸酯酶抑制剂。在目前的工作中，合成 4-oxo-2-phenyl-4 H的常规方法报道了-chromen-7-yl 甲磺酸酯衍生物。它们的细胞毒性通过 MTT 测定对乳腺癌细胞系 (MCF-7) 进行评估。在雌二醇是癌细胞存活的关键生长因子的情况下，与多西紫杉醇相比，评估了最具细胞毒性的化合物3c的凋亡诱导活性，IC 50值为 0.615 µM。双染色Annexin V-FITC/PI分析结果表明该化合物3c在MCF-7细胞中的细胞毒活性通过细胞凋亡发生。进行了分子对接研究以阐明最有希望的化合物（3c）的抑制模式)
• Patonay, Tamas; Molnar, Denes; Muranyi, Zoltan, Bulletin de la Societe Chimique de France, 1995, vol. 132, # 2, p. 233 - 242
  作者：Patonay, Tamas、Molnar, Denes、Muranyi, Zoltan

  DOI：——

  日期：——
• Design, synthesis and evaluation of novel 7-aminoalkyl-substituted flavonoid derivatives with improved cholinesterase inhibitory activities
  作者：Wen Luo、Ying Chen、Ting Wang、Chen Hong、Li-Ping Chang、Cong-Cong Chang、Ya-Cheng Yang、Song-Qiang Xie、Chao-Jie Wang

  DOI：10.1016/j.bmc.2015.12.031

  日期：2016.2

  A novel series of 7-aminoalkyl-substituted flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential cholinesterase inhibitors. The results showed that most of the synthesized compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities at the micromolar range. Compound 2-(naphthalen-1-yl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4-Hchromen-4-one (5q) showed the best inhibitory activity (IC50, 0.64 mu M for AChE and 0.42 mu M for BChE) which were better than our previously reported compounds and the commercially available cholinergic agent Rivastigmine. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5q with AChE and BChE. Furthermore, molecular modeling study showed that 5q targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, these compounds (5a-5r) did not affect PC12 and HepG2 cell viability at the concentration of 10 mu M. Consequently, these flavonoid derivatives should be further investigated as multipotent agents for the treatment of Alzheimer's disease. (c) 2015 Elsevier Ltd. All rights reserved.