4'-Brom-4-methoxy-2'-hydroxy-chalkon | 1226-10-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4'-Brom-4-methoxy-2'-hydroxy-chalkon
• 英文别名: 1-(4-Bromo-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1226-10-4
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: AEBIZIFMJZEYHR-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  490.5±45.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4'-Brom-4-methoxy-2'-hydroxy-chalkon 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 7-Brom-4'-methoxy-flavonol
  参考文献：
  名称：

  Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

  摘要：

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma

  DOI：

  10.1080/07391102.2020.1805364
• 作为产物：
  描述：

  4-溴-2-羟基苯乙酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.5h， 生成 4'-Brom-4-methoxy-2'-hydroxy-chalkon
  参考文献：
  名称：

  Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

  摘要：

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma

  DOI：

  10.1080/07391102.2020.1805364

文献信息

• Discovery of 3-bromoflavone derivative D5 as a novel TLR4-MD2 antagonist for treatment of acute lung injury and sepsis
  作者：Xu Cheng、Yijie Wang、Hao Wang、Jing Xu、Lin Wang、Shouguo Zhang、Shuchen Liu、Tao Peng

  DOI：10.1016/j.molstruc.2024.139375

  日期：2024.12

  Toll-like receptor 4 (TLR4) generates severe inflammatory syndromes such as acute lung injury (ALI) and sepsis, thus targeting TLR4 is attractive as a potential pharmacological therapy for these diseases. The aim of this study is to develop a novel structural TLR4 inhibitor for the treatment of ALI and sepsis. Herein, we designed and synthesized a new series of 3-bromoflavone derivatives by screening

  Toll 样受体 4 (TLR4) 介导的免疫反应的异常激活会产生严重的炎症综合征，例如急性肺损伤 (ALI) 和脓毒症，因此针对 TLR4 作为这些疾病的潜在药物治疗方法具有吸引力。本研究的目的是开发一种新型结构 TLR4 抑制剂，用于治疗 ALI 和脓毒症。在此，我们通过筛选和分子对接设计并合成了一系列新的3-溴黄酮衍生物。通过 ELISA 在巨噬细胞中评估了它们的抗炎作用，并且化合物被确定为最有潜力的抗炎候选物。化合物可抑制脂多糖 (LPS) 诱导的 RAW264.7 细胞中白介素 6 (IL-6) 和肿瘤坏死因子 -α (TNF-α) 的表达，IC 值分别为 0.215 和 4.211 µM。免疫沉淀、SPR 和免疫印迹表明，靶向 TLR4-MD2 复合物并竞争性抑制 LPS 与 TLR4-MD2 的结合，从而抑制 NF-κB 和 MAPK 信号通路。体内给药显着改善LPS诱导的A
• 30. Synthesis of 7-halogenoflavone and related compounds
  作者：F. C. Chen、C. T. Chang

  DOI：10.1039/jr9580000146

  日期：——
• Tuning of environment-sensitive 3-hydroxychromone fluorophores based on strong donor substituents in positions 2 or 7
  作者：Luciana Giordano、Volodymyr V. Shvadchak、Nicolás Arrupe、Lisandro J. Falomir Lockhart、Verónica M. Sánchez、Thomas M. Jovin

  DOI：10.1016/j.dyepig.2023.111479

  日期：2023.10