3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin | 127073-91-0

• 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′,4′-dimethoxyphenyl)-6-methylcoumarin
• 英文别名: 3-(3,4-dimethoxyphenyl)-6-methylchromen-2-one；3-(3,4-dimethoxyphenyl)-6-methylcoumarin
• CAS: 127073-91-0
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: YTRDYTYOUZRVHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C(Solv: ligroine (8032-32-4))
• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 10.67h， 生成 trans-3-(3,4-dimethoxyphenyl)-6-styrylcoumarin
  参考文献：
  名称：

  Synthesis and biological evaluation of resveratrol–coumarin hybrid compounds as potential antitumor agents

  摘要：

  Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3-phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 mu mol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.

  DOI：

  10.1007/s00044-012-0159-y
• 作为产物：
  描述：

  对甲酚 在 硼酸 、 乙酸酐 、 三乙胺 作用下， 以 甘油 为溶剂， 反应 6.17h， 生成 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin
  参考文献：
  名称：

  Synthesis and biological evaluation of resveratrol–coumarin hybrid compounds as potential antitumor agents

  摘要：

  Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3-phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 mu mol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.

  DOI：

  10.1007/s00044-012-0159-y

文献信息

• 3-Arylcoumarins as highly potent and selective monoamine oxidase B inhibitors: Which chemical features matter?
  作者：Marco Mellado、Jaime Mella、César González、Dolores Viña、Eugenio Uriarte、Maria J. Matos

  DOI：10.1016/j.bioorg.2020.103964

  日期：2020.8

  3-arylcoumarins (71–76) based on them. Monoamine oxidase B inhibition is essential to maintain the balance of dopamine, and one of its major functions is to combat dopamine degradation, a phenomenon linked to Parkinson’s disease. In this work, we study small-molecule inhibitors based on the 3-arylcoumarin scaffold and their monoamine oxidase B selective inhibition. We show that 3D-QSAR models, in particular CoMFA

  小分子与酶的相互作用密切调节单胺氧化酶B的抑制活性。因此，期望使用理论方法设计合理的方法以开发新的分子以调节与蛋白质的特异性相互作用。在这里，我们报告这种方法，并通过研究六种合成的3-芳基香豆素说明其成功实施的方法（71 – 76）基于它们。单胺氧化酶B抑制对于维持多巴胺的平衡至关重要，其主要功能之一是抵抗与帕金森氏病有关的多巴胺降解。在这项工作中，我们研究了基于3-芳基香豆素骨架的小分子抑制剂及其单胺氧化酶B的选择性抑制。我们表明3D-QSAR模型，特别是CoMFA和CoMSIA，以及分子对接方法，增加了发现新的有趣抑制剂的可能性，避免了非常昂贵和费时的合成和生物学评估。
• Hans, Naresh; Singhi, Manasi; Sharma, Vibha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 11, p. 1159 - 1162
  作者：Hans, Naresh、Singhi, Manasi、Sharma, Vibha、Grover

  DOI：——

  日期：——
• Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2<i>H</i>-2-chromenone (AP2238) Derivatives
  作者：Lorna Piazzi、Andrea Cavalli、Federica Belluti、Alessandra Bisi、Silvia Gobbi、Stefano Rizzo、Manuela Bartolini、Vincenza Andrisano、Maurizio Recanatini、Angela Rampa

  DOI：10.1021/jm070100g

  日期：2007.8.1

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.
• Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins
  作者：Maria João Matos、Fernanda Pérez-Cruz、Saleta Vazquez-Rodriguez、Eugenio Uriarte、Lourdes Santana、Fernanda Borges、Claudio Olea-Azar

  DOI：10.1016/j.bmc.2013.04.015

  日期：2013.7

  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.
• Synthesis and Study of a Series of 3-Arylcoumarins as Potent and Selective Monoamine Oxidase B Inhibitors
  作者：Maria J. Matos、Carmen Terán、Yunierkis Pérez-Castillo、Eugenio Uriarte、Lourdes Santana、Dolores Viña

  DOI：10.1021/jm200716y

  日期：2011.10.27

  New series of 6-substituted-3-arylcoumarins displaying several alkyl, hydroxyl, halogen, and alkoxy groups in the two benzene rings have been designed, synthesized, and evaluated in vitro as human monoamine cuddase A and B (hMAO-A and hMAO-B) inhibitors. Most of the studied compounds showed a high affinity and selectivity to the hMAO-B isoenzyme, with IC50 values on nanomolar and picomolar range. Ten of the 22 described compounds displayed higher MAO-B inhibitory activity and selectivity than selegiline. Coumarin 7 is the most active compound of this series, being 64 times more active than selegiline and also showing the highest hMAO-B specificity. In addition, docking experiments were carried out on hMAO-A and h-MAO-B structures. This study provided new information about the enzyme inhibitor interaction and the potential therapeutic application of this 3-arylcoumarin scaffold.