3-(3′-aminophenyl)-6-methylcoumarin

• 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′-aminophenyl)-6-methylcoumarin
• 英文别名: 3-(3-Aminophenyl)-6-methylchromen-2-one；3-(3-aminophenyl)-6-methylchromen-2-one
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: LGZDIVLUIURHFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-methyl-3-(3′-nitrophenyl)coumarin 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%的产率得到3-(3′-aminophenyl)-6-methylcoumarin
  参考文献：
  名称：

  Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives

  摘要：

  In this study we synthesized and evaluated a new series of amino and nitro 3-arylcoumarins as hMAO-A and hMAO-B inhibitors. Compounds 2, 3, 5 and 6 presented a better activity and selectivity profile against the hMAO-B isoform (IC50 values between 2 and 6 nM) than selegiline. In general, the amino derivatives (4-6) proved to be more selective against MAO-B than the nitro derivatives (1-3). Additionally, a theoretical study of some physicochemical properties, PAMPA and reversibility assays for the most potent derivative, and molecular docking simulations were carried out to further explain the pharmacological results, and to identify the hypothetical binding mode for the compounds inside the hMAO-B. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.001

文献信息

• Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
  作者：Maria João Matos、Fernanda Rodríguez-Enríquez、Santiago Vilar、Lourdes Santana、Eugenio Uriarte、George Hripcsak、Martín Estrada、María Isabel Rodríguez-Franco、Dolores Viña

  DOI：10.1016/j.bmcl.2014.12.001

  日期：2015.2

  In this study we synthesized and evaluated a new series of amino and nitro 3-arylcoumarins as hMAO-A and hMAO-B inhibitors. Compounds 2, 3, 5 and 6 presented a better activity and selectivity profile against the hMAO-B isoform (IC50 values between 2 and 6 nM) than selegiline. In general, the amino derivatives (4-6) proved to be more selective against MAO-B than the nitro derivatives (1-3). Additionally, a theoretical study of some physicochemical properties, PAMPA and reversibility assays for the most potent derivative, and molecular docking simulations were carried out to further explain the pharmacological results, and to identify the hypothetical binding mode for the compounds inside the hMAO-B. (C) 2014 Elsevier Ltd. All rights reserved.