3-(3-methoxyphenyl)-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-(3-methoxyphenyl)-7-hydroxycoumarin
• 英文别名: 7-hydroxy-3-(3’-methoxyphenyl) coumarin；7-hydroxy-3-(3-methoxyphenyl)-2H-chromen-2-one；7-hydroxy-3-(3-methoxyphenyl)coumarin；7-Hydroxy-3-(3-methoxy-phenyl)-cumarin；7-hydroxy-3-(3-methoxyphenyl)chromen-2-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: OUWCJEVIJWQBGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-methoxyphenyl)-7-hydroxycoumarin 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以83%的产率得到E-2,4-dihydroxy-3’-methoxystilbene
  参考文献：
  名称：

  α，β-不饱和芳族内酯的脱羧作用：由3-芳基香豆素或异金龙酮合成E-邻-羟基对苯二酚

  摘要：

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。

  DOI：

  10.1039/c7gc02994b
• 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-(3-methoxyphenyl)-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

• 一种3-芳基香豆素类衍生物及其制备方法和用途
  申请人：中山大学

  公开号：CN113121485B

  公开（公告）日：2023-01-03

  本发明公开了一种3‑芳基香豆素类衍生物及其制备方法和用途，是以取代苯乙酸和取代2‑羟基苯甲醛为原料，在三乙胺和乙酸酐存在下，发生串联的缩合‑内酯化反应，反应完毕后，再各自独立地经三种后处理方法得到3‑芳基香豆素类衍生物。本发明提供的3‑芳基香豆素类衍生物对SIRT3蛋白具有良好的亲和力，并能上调SIRT3蛋白的去乙酰化酶活性，逆转ISO(异丙肾上腺素)刺激诱导的心肌肥厚，可用于制备抗心血管疾病或抗糖尿病药物。
• New flavonoid-containing derivatives of lupinine
  作者：S. P. Bondarenko、M. S. Frasinyuk、A. I. Galaev、V. I. Vinogradova

  DOI：10.1007/s10600-012-0212-6

  日期：2012.5

  An oxazine ring was annelated to benzopyran-4-one and benzopyran-2-one cores by reacting 7-hydroxyisoflavones and 7-hydroxycoumarins with lupinylamine and formalin. The new derivatives 9,10-dihydro4H,8 H-chromeno[8,7-e][1,3]oxazin-4-one and 9,10-dihydro-2 H,8 H-chromeno[8,7-e][1,3]oxazin-2-one containing a lupinine moiety in the 9-position were prepared.

  7-hydroxyisoflavones and 7-hydroxycoumarins with lupinylamine and formalin reactated an oxazine ring to benzopyran-4-one and benzopyran-2-one cores.制备出了 9,10-二氢-4H,8 H-色烯并[8,7-e][1,3]恶嗪-4-酮和 9,10-二氢-2 H,8 H-色烯并[8,7-e][1,3]恶嗪-2-酮的新衍生物，其 9 位含有羽扇豆碱分子。
• Reduction of Phenols. New Synthesis of Oxyhexahydro-3-ketophenanthrenes by Cyclodehydration of 4-(β-Arylethyl)-1,3-cyclohexandiones
  作者：Gordon N. Walker

  DOI：10.1021/ja01536a037

  日期：1958.2
• Kirkiacharian; Lormier; Resche-Rigon, Annales Pharmaceutiques Francaises, 2003, vol. 61, # 1, p. 51 - 56
  作者：Kirkiacharian、Lormier、Resche-Rigon、Bouchoux、Cérède

  DOI：——

  日期：——
• Decarboxylation of α,β-unsaturated aromatic lactones: synthesis of<i>E-ortho</i>-hydroxystilbenes from 3-arylcoumarins or isoaurones
  作者：Xihua Huang、Jie Liu、Jianfei Sheng、Xianheng Song、Zhibo Du、Mingkang Li、Xuejing Zhang、Yong Zou

  DOI：10.1039/c7gc02994b

  日期：——

  A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。