3-(o-methoxyphenyl)-6-methylcoumarin | 1190439-39-4

• 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-(o-methoxyphenyl)-6-methylcoumarin
• 英文别名: 3-(2'-methoxy)phenyl-6-methylcoumarin；3-(2-Methoxyphenyl)-6-methylchromen-2-one
• CAS: 1190439-39-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: VOFSENJXRIQEMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(o-methoxyphenyl)-6-methylcoumarin 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 以56%的产率得到3-(2-hydroxyphenyl)-6-methylcoumarin
  参考文献：
  名称：

  Synthesis and Study of a Series of 3-Arylcoumarins as Potent and Selective Monoamine Oxidase B Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm200716y
• 作为产物：
  描述：

  5-甲基水杨醛 、 2-甲氧基苯乙酸 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， 以59%的产率得到3-(o-methoxyphenyl)-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-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）。
• 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.
• 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.
• Comparative study of the 3-phenylcoumarin scaffold: Synthesis, X-ray structural analysis and semiempirical calculations of a selected series of compounds
  作者：Maria J. Matos、Santiago Vilar、Nicholas P. Tatonetti、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/j.molstruc.2013.07.037

  日期：2013.10

  comparative study between compounds 1, 2 and 3, based on the structural results, was carried out. In addition, the X-ray structures were compared to those obtained combining conformational analysis with semiempirical methodologies (AM1 and PM3). The results provided by the semiempirical calculations in gas phase are in strong agreement with the X-ray method for the three molecules under study, meaning

  摘要 通过 Perkin 反应合成了化合物 1（6-甲基-3-苯基香豆素）、2（3-（邻甲氧基苯基）-6-甲基香豆素）和 3（3-（间甲氧基苯基）-6-甲基香豆素）。 2-羟基-5-甲基苯甲醛和相应的苯乙酸。1H 和 13C NMR 和 X 射线衍射测定了衍生物的分子结构。基于结构结果，对化合物 1、2 和 3 进行了比较研究。此外，将 X 射线结构与结合构象分析和半经验方法（AM1 和 PM3）获得的结构进行了比较。气相半经验计算提供的结果与所研究的三个分子的 X 射线方法非常一致，