7,8-dihydroxy-3-(4'-hydroxyphenyl)coumarin | 97192-90-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7,8-dihydroxy-3-(4'-hydroxyphenyl)coumarin
• 英文别名: 7,8-Dihydroxy-3-(4-hydroxyphenyl)chromen-2-one；7,8-dihydroxy-3-(4-hydroxyphenyl)chromen-2-one
• CAS: 97192-90-0
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: SHWFFEHIZXPZOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7,8-diacetoxy-3-(4-acetoxyphenyl)coumarin 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以91%的产率得到7,8-dihydroxy-3-(4'-hydroxyphenyl)coumarin
  参考文献：
  名称：

  Structure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists

  摘要：

  Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by our group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A(3) receptor antagonists were found. 3-(4-Bromophenyl)-8-hydroxycoumarin (compound 4) displayed the highest potency and selectivity as A(3) receptor antagonist (K-i = 258 nM). An analysis of its X-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theoretical modeling calculations corroborate and explain the experimental data, suggesting this novel scaffold can be involved in the generation of candidates as multitarget drugs.

  DOI：

  10.1021/acs.jmedchem.9b01572

文献信息

• Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
  作者：Jie Yang、Pingping Zhang、Yuheng Hu、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2019.1574297

  日期：2019.1.1

  the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited

  抽象的 阿尔茨海默氏病是一种神经退行性疾病，其发病机理极为复杂。越来越多的证据表明，几种酶与阿尔茨海默氏病之间存在密切的关系。合成了各种取代的3-芳基香豆素衍生物，并研究了它们的体外活性，包括胆碱酯酶抑制活性，单胺氧化酶抑制活性和抗氧化活性。大多数化合物表现出高活性。因此3-芳基香豆素类化合物具有治疗阿尔茨海默氏病的潜力。
• Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
  作者：Yuheng Hu、Bing Wang、Jie Yang、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2018.1518958

  日期：2019.1.1

  Abstract A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs)

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。
• [EN] CANCER METASTASIS INHIBITOR<br/>[FR] INHIBITEUR DE MÉTASTASES CANCÉREUSES<br/>[JA] 癌転移抑制剤
  申请人：KYOTO PHARMACEUTICAL UNIV

  公开号：WO2020130120A1

  公开（公告）日：2020-06-25

  本発明は、新規な癌転移抑制剤に関する。本発明によれば、式（Ｉ）： [式中の各記号の定義は、明細書に記載の通りである。] で表される化合物、又はその医薬上許容される塩を有効成分として含有することを特徴とする癌転移抑制剤を提供することができる。
• Structure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists
  作者：Maria João Matos、Santiago Vilar、Saleta Vazquez-Rodriguez、Sonja Kachler、Karl-Norbert Klotz、Michela Buccioni、Giovanna Delogu、Lourdes Santana、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.9b01572

  日期：2020.3.12

  Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by our group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A(3) receptor antagonists were found. 3-(4-Bromophenyl)-8-hydroxycoumarin (compound 4) displayed the highest potency and selectivity as A(3) receptor antagonist (K-i = 258 nM). An analysis of its X-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theoretical modeling calculations corroborate and explain the experimental data, suggesting this novel scaffold can be involved in the generation of candidates as multitarget drugs.