3-(4'-hydroxy)phenyl-6-methylcoumarin | 1190439-40-7

• 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-(4'-hydroxy)phenyl-6-methylcoumarin
• 英文别名: 3-(4-hydroxyphenyl)-6-methylcoumarin；3-(4-hydroxyphenyl)-6-methyl-2H-chromen-2-one；3-(4-hydroxyphenyl)-6-methylchromen-2-one
• CAS: 1190439-40-7
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: JSHUCMRTLUIFTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4'-hydroxy)phenyl-6-methylcoumarin 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 6-methyl-3-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and evaluation of 6-substituted 3-arylcoumarin derivatives as multifunctional acetylcholinesterase/monoamine oxidase B dual inhibitors for the treatment of Alzheimer’s disease

  摘要：

  化合物5o和5p均为治疗阿尔茨海默病的多功能hAChE/hMAO-B双重抑制剂。

  DOI：

  10.1039/c5ra22296f
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-6-methyl-2H-chromen-2-one 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 5.0h， 以63%的产率得到3-(4'-hydroxy)phenyl-6-methylcoumarin
  参考文献：
  名称：

  作为有效和选择性MAO-B抑制剂的6-甲基-3-苯基香豆素的合成和评价

  摘要：

  合成了一系列6-甲基-3-苯基香豆素3-6，并作为单胺氧化酶A和B（MAO-A和MAO-B）抑制剂进行了评估。报道了三种可能的单甲氧基3-苯基衍生物与对羟基类似物的比较研究。这些新的白藜芦醇-香豆素杂化物的合成是通过5-甲基水杨醛和相应的苯乙酸之间的珀金反应进行的。该p取代的化合物-甲氧基3水解成6通过用氢碘酸传统反应。制备的化合物对MAO-B同工酶具有很高的选择性，其中一些IC 50值在低纳摩尔范围内。化合物4，其中甲氧基位于间位，是该系列中最活跃的，对MAO-B的IC 50为0.80 nM，并且比R -（-）-去异戊二烯基（参考化合物）。

  DOI：

  10.1016/j.bmcl.2009.07.039

文献信息

• Synthesis and evaluation of 6-methylcoumarin derivatives as potent and selective monoamine oxidase B inhibitors
  作者：Jin-Shuai Lan、Long-Fei Pan、Sai-Sai Xie、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1039/c4md00437j

  日期：——

  Compound5nwas a potent and selective inhibitor of hMAO-B.

  化合物5n是一种有效且选择性抑制剂，可抑制hMAO-B。
• 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.
• Synthesis and evaluation of 6-substituted 3-arylcoumarin derivatives as multifunctional acetylcholinesterase/monoamine oxidase B dual inhibitors for the treatment of Alzheimer’s disease
  作者：Zhi-Min Wang、Xue-Mei Li、Gui-Min Xue、Wei Xu、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1039/c5ra22296f

  日期：——

  Compounds5oand5pwere both multifunctional hAChE/hMAO-B dual inhibitors for the treatment of AD.

  化合物5o和5p均为治疗阿尔茨海默病的多功能hAChE/hMAO-B双重抑制剂。
• Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors
  作者：Maria Joao Matos、Dolores Viña、Carmen Picciau、Francisco Orallo、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/j.bmcl.2009.07.039

  日期：2009.9

  A series of 6-methyl-3-phenylcoumarins 3-6 were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. A comparative study between the three possible mono methoxy 3-phenyl derivatives and the p-hydroxy analogue is reported. The synthesis of these new resveratrol-coumarin hybrids was carried out by a Perkin reaction between the 5-methylsalicylaldehyde and the corresponding

  合成了一系列6-甲基-3-苯基香豆素3-6，并作为单胺氧化酶A和B（MAO-A和MAO-B）抑制剂进行了评估。报道了三种可能的单甲氧基3-苯基衍生物与对羟基类似物的比较研究。这些新的白藜芦醇-香豆素杂化物的合成是通过5-甲基水杨醛和相应的苯乙酸之间的珀金反应进行的。该p取代的化合物-甲氧基3水解成6通过用氢碘酸传统反应。制备的化合物对MAO-B同工酶具有很高的选择性，其中一些IC 50值在低纳摩尔范围内。化合物4，其中甲氧基位于间位，是该系列中最活跃的，对MAO-B的IC 50为0.80 nM，并且比R -（-）-去异戊二烯基（参考化合物）。