3-(4-fluorophenyl)-7-hydroxycoumarin

• 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: 3-(4-fluorophenyl)-7-hydroxycoumarin
• 英文别名: 3-(4-fluorophenyl)-7-hydroxy-2H-chromen-2-one；7-hydroxy-3-(4-fluorophenyl)coumarin；3-(4-fluorophenyl)-7-hydroxychromen-2-one
• 化学式: C₁₅H₉FO₃
• mdl: MFCD06001478
• 分子量: 256.233
• InChiKey: XXDAXGKPCUCYLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-7-hydroxycoumarin 在 potassium tert-butylate 、 四丁基溴化铵 、 potassium iodide 作用下， 以 二苯醚 、 乙腈 为溶剂， 反应 9.0h， 生成 3-(4'-fluorophenyl)-2"H-7,8-pyrancoumarin
  参考文献：
  名称：

  3-芳基-7,8-吡喃香豆素衍生物及其制备方法和应用

  摘要：

  本发明公开了一种3‑芳基‑7,8‑吡喃香豆素衍生物，该衍生物具有通式Ⅰ所示的结构，本发明公开了一种3‑芳基‑7,8‑吡喃香豆素衍生物的制备方法，包括：将苯乙酸取代物、醋酸酐、三乙胺、2，4‑二甲羟基苯甲醛混合反应，经提纯得到3‑苯基香豆素衍生物；将3‑苯基香豆素衍生物、乙腈、叔丁醇钾、碘化钾、四丁基溴化铵、炔化物混合反应，经提纯得到炔丙基醚类化合物；将炔丙基醚类化合物和二苯醚混合反应，经提纯得到目标化合物I，该制备方法具有收率高、底物适用性广的有益效果。本发明公开了3‑芳基‑7,8‑吡喃香豆素衍生物在制备抗肿瘤药物中的应用。

  公开号：

  CN115073485A
• 作为产物：
  描述：

  4-((tert-butyldimethylsilyl)oxy)-2-hydroxybenzaldehyde 在 N-甲基吗啉 、 三聚氯氰 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-(4-fluorophenyl)-7-hydroxycoumarin
  参考文献：
  名称：

  7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor

  摘要：

  Macrophage migration inhibitory factor (MIF) is a cytokine with key roles in inflammation and cancer, which qualifies it as a potential drug target. Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization. MIF enzymatic activity has been used for identification of MIF binding molecules that also interfere with its biological activity. However, MIF tautomerase activity assays are troubled by irregularities, thus creating a need for alternative methods. In this study, we identified a 7-hydroxycoumarin fluorophore with high affinity for the MIF tautomerase active site (Ki = 18 ± 1 nM) that binds with concomitant quenching of its fluorescence. This property enabled development of a novel competition-based assay format to quantify MIF binding. We also demonstrated that the 7-hydroxycoumarin fluorophore interfered with the MIF-CD74 interaction and inhibited proliferation of A549 cells. Thus, we provide a high-affinity MIF binder as a novel tool to advance MIF-oriented research.

  DOI：

  10.1021/acs.jmedchem.0c01160

文献信息

• Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
  作者：Parul Chauhan、Makthala Ravi、Shikha Singh、Prashant Prajapati、Prem P. Yadav

  DOI：10.1039/c5ra20954d

  日期：——

  A transition-metal-free regioselective α-arylation of coumarins and 2-pyridones has been accomplished by the reaction of phenylhydrazines with coumarins or 2-pyridones.

  一种无过渡金属的选择性α-芳基化反应已经成功实现，通过苯基肼与香豆素或2-吡啶酮的反应。
• 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。
• Modified coumarins. 29. Synthesis of structural analogs of natural 6-arylfuro[3,2-g]chromen-7-ones
  作者：M. M. Garazd、Ya. L. Garazd、A. S. Ogorodniichuk、V. P. Khilya

  DOI：10.1007/s10600-009-9261-x

  日期：2009.3

  3-Substituted 6-arylfuro[3,2-g]chromen-7-ones, structural analogs of natural furocoumarins, were synthesized by linear annelation of a furan fragment to a 3-arylcoumarin system.

  3-取代的6-芳基呋喃[3,2-g]色烯-7-酮，作为天然呋喃香豆素的结构类似物，通过将呋喃片段线性连接到3-芳基香豆素体系中合成。
• Conjugation of the Alkaloid Anabasine to Coumarins
  作者：S. P. Bondarenko、G. P. Mrug、V. I. Vinogradova、V. P. Khilya、M. S. Frasinyuk

  DOI：10.1007/s10600-019-02765-w

  日期：2019.7

  The possibility of using the alkaloid anabasine in Mannich aminomethylation of coumarins was studied. Anabasine-coumarin conjugates in which the benzopyrone core was conjugated to anabasine through a methylene linker were synthesized.

  研究了在香豆素的曼尼希氨甲基化中使用生物碱鱼腥草碱的可能性。合成了 Anabasine-香豆素缀合物，其中苯并吡喃酮核通过亚甲基接头与 anabasine 缀合。