3-(3,5-dimethoxyphenyl)-7-hydroxycoumarin | 873869-44-4

• 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-(3,5-dimethoxyphenyl)-7-hydroxycoumarin
• 英文别名: 7-hydroxy-3-(3’,5’-dimethoxyphenyl)coumarin；3-(3,5-Dimethoxyphenyl)-7-hydroxy-2H-1-benzopyran-2-one；3-(3,5-dimethoxyphenyl)-7-hydroxychromen-2-one
• CAS: 873869-44-4
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: WXKGVVRNONGIIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,5-dimethoxyphenyl)-7-hydroxycoumarin 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以84%的产率得到3',5'-dimethoxy-2,4-dihydroxystilbene
  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：

  7-acetyloxy-3-(3',5'-dimethoxyphenyl)coumarin 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到3-(3,5-dimethoxyphenyl)-7-hydroxycoumarin
  参考文献：
  名称：

  Hydroxyl Substitutional Effect on Selective Synthesis of cis, trans Stilbenes and 3-Arylcoumarins Through Perkin Condensation

  摘要：

  The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarins has been described. The regio- and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence or absence of hydroxyl group as well as their positions in the phenyl ring. As a result, practical synthetic strategies were established for preparing various natural stilbenes including combretastatin A-4, pterostilbene, and resveratrol with satisfactory yields (49.2-63.7%).

  DOI：

  10.1080/00397911.2010.538889

文献信息

• 一种反式邻羟基二苯乙烯类化合物的制备方 法
  申请人：广州中大南沙科技创新产业园有限公司

  公开号：CN106699519B

  公开（公告）日：2019-09-17

  本发明公开了一种反式邻羟基二苯乙烯类化合物的制备方法，是在溶剂和碱的存在下，3‑芳基香豆素类化合物发生开环脱羧反应，再经后处理，得到反式邻羟基二苯乙烯类化合物。本发明的底物适用范围广，反式选择性高，溶剂环境友好，脱羧过程无需使用金属催化剂，工艺过程绿色环保。
• Resveratrol derivatives: Synthesis and their biological activities
  作者：Laura Grau、Richard Soucek、M. Dolors Pujol

  DOI：10.1016/j.ejmech.2022.114962

  日期：2023.1

  its antioxidant properties and protective action, opens the door for both it and its structural derivatives to be considered not only as chemopreventive but also as cancer chemotherapeutic agents. Due to the pharmacokinetic problems of resveratrol that demonstrate its poor bioavailability, the study of new derivatives is of interest. Thus, in this work (E)-stilbenes derived directly from resveratrol

  白藜芦醇是一种以其抗氧化特性和保护作用而闻名的天然化合物，它为其及其结构衍生物打开了大门，使其不仅被视为化学预防剂，而且被视为癌症化学治疗剂。由于白藜芦醇的药代动力学问题表明其生物利用度差，因此对新衍生物的研究引起了人们的兴趣。因此，在这项工作中，已经合成了直接衍生自白藜芦醇和其他含有苯并呋喃或吲哚核的环状类似物的 ( E )-二苯乙烯。已经评估了合成化合物在体外影响肿瘤生长的能力。化合物2 , 3 , 4和5已显示在人结肠癌 (HT-29) 和人胰腺癌细胞 (MIA PaCa-2) 中的细胞毒性高于 ( E )-白藜芦醇。吲哚衍生物13是白藜芦醇的一种环状类似物，在体外显示出对 HT-29 癌细胞的细胞毒活性比白藜芦醇高 8 倍。环状衍生物8、9和12在20 μM 时显示出对 HCT-116（KRas 突变体）细胞生长的高度抑制，而13在10 μM 时显示出中等的抗血管生成活性。
• Design, synthesis and antitumor activity of a series of novel coumarin–stilbenes hybrids, the 3-arylcoumarins
  作者：Chun Fen Xiao、Li Yang Tao、Hong Yi Sun、Wen Wei、Yu Chen、Li Wu Fu、Yong Zou

  DOI：10.1016/j.cclet.2010.04.034

  日期：2010.11

  A series of novel coumarin-stilbenes hybrids called 3-arylcoumarins were synthesized via Perkin reaction and evaluated as potential antitumor agents. The results showed that some compounds exhibited in vitro activity against KB, KV, MCF-7, MCF-7/ADR cell lines to some extent. Compound 3a showed remarkable effect against KB tumor cells with an IC50 value of 5.18 mu mol/L. (C) 2010 Yong Zou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin–resveratrol hybrids
  作者：Santiago Vilar、Elías Quezada、Lourdes Santana、Eugenio Uriarte、Matilde Yánez、Nuria Fraiz、Carlos Alcaide、Ernesto Cano、Francisco Orallo

  DOI：10.1016/j.bmcl.2005.10.013

  日期：2006.1

  We have synthesized the coumarin-resveratrol hybrid 4 and its dimethoxy derivative 3 by a very direct synthetic route involving a Pechmann procedure. Compound 4 has also been synthesized by an alternative route (Perkin), which also allowed the synthesis of compounds 9-13. In addition, we have evaluated the potential vasorelaxant activity of the new compounds in endothelium-containing rat aorta rings pre-contracted with noradrenaline, as well as the inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. The compounds reported here relaxed vascular smooth muscle and inhibited platelet aggregation with a profile similar to that of trans-resveratrol (t-RESV) and, in some cases, showed activity higher than that of the natural compound. This is the case for compound 13, which has a vasorelaxant activity that is twice as high as that of t-resveratrol and a platelet antiaggregant activity that is six times higher. These results suggest that these novel compounds may have potential as structural templates for the design and subsequent development of new vasodilatory and platelet antiaggregatory drugs. (c) 2005 Elsevier Ltd. All rights reserved.
• 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。