8-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one | 59276-88-9

• 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-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one
• 英文别名: 8-methoxy-3-(4’-methoxyphenyl)coumarin；8-methoxy-3-(4'-methoxyphenyl)coumarin；3-(4-methoxyphenyl)-8-methoxycoumarin；8-methoxy-3-(4-methoxyphenyl)coumarin；8-methoxy-3-(4-methoxy-phenyl)-chromen-2-one；8-Methoxy-3-(4-methoxyphenyl)-cumarin；8-methoxy-3-(4-methoxyphenyl)chromen-2-one
• CAS: 59276-88-9
• 化学式: C₁₇H₁₄O₄
• mdl: MFCD00774695
• 分子量: 282.296
• InChiKey: PUCPZDZHLAJZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 生成 8-hydroxy-3-(4-hydroxyphenyl)-coumarin
  参考文献：
  名称：

  Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins

  摘要：

  In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried. out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.015
• 作为产物：
  描述：

  2-hydroxy-4',8-dimethoxyisoflav-3-ene 在 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以85%的产率得到8-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  A synthesis of 2,4-dihydroxyisoflavans and 2-Hydroxyisoflav-3-enes: Versatile precursors to isoflavanoids

  摘要：

  通过将水杨醛与芳基甘氨酸盐进行处理，开发出了一种新的异黄酮合成方法。 水杨醛与芳基甘氨酸盐的新合成方法。反应条件 条件，使这种缩合反应可以生成 2,4-二羟基异黄烷或 2-羟基异黄烷-3-烯。2- 羟基异黄-3-烯 如 (8a)，然后可以转化成异黄烷鎓盐 (9b)、异黄烷鎓盐 (9b) 盐 (9b)、异黄烷 (11b)、 2-羟基异黄烷（11a）、异黄酮-2-烯（13）或异黄酮-3-烯（10d）。类似地 2-氨基异黄-3-烯衍生物（10f）可由（8d）得到。反应 异黄酮盐或 (8a) 与 3-巯基丙酸反应，可得到异黄酮-3-烯衍生物（15）。 作为触媒，可与合适的大分子共轭，生成 与合适的大分子共轭，从而产生抗体。

  DOI：

  10.1071/ch9842545

文献信息

• 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。
• A transition-metal-free fast track to flavones and 3-arylcoumarins
  作者：Mostafa Golshani、Mehdi Khoobi、Nafiseh Jalalimanesh、Farnaz Jafarpour、Alireza Ariafard

  DOI：10.1039/c7cc02107k

  日期：——

  The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

  使用K 2 S 2 O 8，实现了色农酮与芳基硼酸的高度区域选择性和无过渡金属的一锅芳基化反应。该程序由一系列反应组成，包括芳基化/脱羧级联，并在水性介质中进行得很好，从而提供了生物学上令人感兴趣的黄酮和3-芳基香豆素。该方法在温和条件下显示出极好的选择性和官能团耐受性。该反应还显示出制备苯乙烯基香豆素的完美功效。
• 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
• Palladium-Catalyzed Decarboxylative Cross-Coupling Reactions: A Route for Regioselective Functionalization of Coumarins
  作者：Farnaz Jafarpour、Samaneh Zarei、Mina Barzegar Amiri Olia、Nafiseh Jalalimanesh、Soraya Rahiminejadan

  DOI：10.1021/jo302778d

  日期：2013.4.5

  A straightforward, regioselective, and step-economical ligand-free palladium-catalyzed decarboxylative functionalization of coumarin-3-carboxylic acids is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows for construction of various biologically important π-electron extended coumarins.

  设计了一种直接的，区域选择性的，经济的，无配体的，香豆素-3-羧酸无钯催化的脱羧功能化方法。该方案与各种各样的供电子和撤电子取代基兼容，并允许构建各种生物学上重要的π电子扩展香豆素。
• 2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis
  作者：Wenchen Pu、Yun Yuan、Danfeng Lu、Xin Wang、Hanwei Liu、Chun Wang、Fei Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2016.10.013

  日期：2016.11

  2-phenylbenzo[b]furan glycosides could promote estrogen biosynthesis. To find high active 2-phenylbenzo[b]furans, fifty-four 2-phenylbenzo[b]furans were prepared via four strategies according to corresponding substrate scopes. Biological evaluation in HEK293A cells showed that some compounds exhibited promotive activity on estrogen biosynthesis. 2-(4-Chlorophenyl)-7-methoxybenzo[b]furan possessed the

  雌激素的生物合成对人类的许多生理过程至关重要。雌激素水平异常与多种疾病密切相关，包括乳腺癌和骨质疏松症。以前我们发现2-苯基苯并[b]呋喃糖苷可以促进雌激素的生物合成。为了找到高活性的2-苯基苯并[b]呋喃，根据相应的底物范围，通过四种策略制备了五十四种2-苯基苯并[b]呋喃。HEK293A细胞的生物学评估表明，某些化合物对雌激素的生物合成具有促进作用。2-（4-氯苯基）-7-甲氧基苯并[b]呋喃具有最高的活性，EC50值为14.68μM。此外，这些化合物不会影响HEK292A细胞中的芳香化酶表达，