8-ethoxy-3-(4'-methoxyphenyl)coumarin | 1312587-24-8

• 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: 8-ethoxy-3-(4'-methoxyphenyl)coumarin
• 英文别名: 8-Ethoxy-3-(4''-methoxyphenyl)coumarin；8-ethoxy-3-(4-methoxyphenyl)chromen-2-one
• CAS: 1312587-24-8
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: MZYDUIAIVPQMQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-ethoxy-3-(4'-methoxyphenyl)coumarin 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 以61%的产率得到8-hydroxy-3-(4-hydroxyphenyl)-coumarin
  参考文献：
  名称：

  New halogenated phenylcoumarins as tyrosinase inhibitors

  摘要：

  With the aim to find out structural features for the tyrosinase inhibitory activity, in the present communication we report the synthesis and pharmacological evaluation of a new series of phenylcoumarin derivatives with different number of hydroxyl or ether groups and bromo substituent in the scaffold. The synthesized compounds 5-12 were evaluated as mushroom tyrosinase inhibitors showing, two of them, lower IC50 than the umbelliferone. Compound 12 (IC50 = 215 mu M) is the best tyrosinase inhibitor of this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.012
• 作为产物：
  描述：

  对甲氧基苯乙酸 、 3-乙氧基水杨醛 在 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 8-ethoxy-3-(4'-methoxyphenyl)coumarin
  参考文献：
  名称：

  2芳基苯并呋喃与3芳香豆素的MAO抑制活性：合成，体外研究和对接计算

  摘要：

  单胺氧化酶（MAO）是治疗神经系统疾病的重要药物靶标。以前有几种3-芳基香豆素衍生物被描述为有趣的选择性MAO-B抑制剂。保留了反式二苯乙烯结构，合成了一系列的2-芳基苯并呋喃衍生物和相应的3-芳基香豆素衍生物，并将其评估为MAO-A和MAO-B的抑制剂。通常，发现两种类型的衍生物都是选择性的MAO-B抑制剂，IC 50值在纳摩尔至微摩尔范围内。5-硝基-2-（4-甲氧基苯基）苯并呋喃（8）是苯并呋喃系列中活性最高的化合物，具有MAO-B选择性和可逆抑制作用（IC 50 = 140 n M）。具有与化合物8相同的取代模式的3-（4'-甲氧基苯基）-6-硝基香豆素（15）被发现是香豆素系列中活性最高的MAO-B抑制剂（IC 50 = 3 n M） 。但是，3-苯基香豆素14的活性在相同范围内（IC 50 = 6 n M），可逆，并且选择性也比化合物15高出几倍。将最具活性的化合物对接到MAO

  DOI：

  10.1002/cmdc.201300048

文献信息

• MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, in vitro Study, and Docking Calculations
  作者：Giulio Ferino、Enzo Cadoni、Maria João Matos、Elias Quezada、Eugenio Uriarte、Lourdes Santana、Santiago Vilar、Nicholas P. Tatonetti、Matilde Yáñez、Dolores Viña、Carmen Picciau、Silvia Serra、Giovanna Delogu

  DOI：10.1002/cmdc.201300048

  日期：2013.6

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3‐arylcoumarin derivatives were previously described as interesting selective MAO‐B inhibitors. Preserving the trans‐stilbene structure, a series of 2‐arylbenzofuran and corresponding 3‐arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO‐A and MAO‐B. In general

  单胺氧化酶（MAO）是治疗神经系统疾病的重要药物靶标。以前有几种3-芳基香豆素衍生物被描述为有趣的选择性MAO-B抑制剂。保留了反式二苯乙烯结构，合成了一系列的2-芳基苯并呋喃衍生物和相应的3-芳基香豆素衍生物，并将其评估为MAO-A和MAO-B的抑制剂。通常，发现两种类型的衍生物都是选择性的MAO-B抑制剂，IC 50值在纳摩尔至微摩尔范围内。5-硝基-2-（4-甲氧基苯基）苯并呋喃（8）是苯并呋喃系列中活性最高的化合物，具有MAO-B选择性和可逆抑制作用（IC 50 = 140 n M）。具有与化合物8相同的取代模式的3-（4'-甲氧基苯基）-6-硝基香豆素（15）被发现是香豆素系列中活性最高的MAO-B抑制剂（IC 50 = 3 n M） 。但是，3-苯基香豆素14的活性在相同范围内（IC 50 = 6 n M），可逆，并且选择性也比化合物15高出几倍。将最具活性的化合物对接到MAO
• 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.
• New halogenated phenylcoumarins as tyrosinase inhibitors
  作者：Maria João Matos、Lourdes Santana、Eugenio Uriarte、Giovanna Delogu、Marcella Corda、Maria Benedetta Fadda、Benedetta Era、Antonella Fais

  DOI：10.1016/j.bmcl.2011.04.012

  日期：2011.6

  With the aim to find out structural features for the tyrosinase inhibitory activity, in the present communication we report the synthesis and pharmacological evaluation of a new series of phenylcoumarin derivatives with different number of hydroxyl or ether groups and bromo substituent in the scaffold. The synthesized compounds 5-12 were evaluated as mushroom tyrosinase inhibitors showing, two of them, lower IC50 than the umbelliferone. Compound 12 (IC50 = 215 mu M) is the best tyrosinase inhibitor of this series. (C) 2011 Elsevier Ltd. All rights reserved.