(+)-2-methoxy-6-(10'-hydroxypentadec-80(E)-enyl)benzoic acid methyl ester | 1314555-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-2-methoxy-6-(10'-hydroxypentadec-80(E)-enyl)benzoic acid methyl ester
• 英文别名: methyl 2-[(E,10S)-10-hydroxypentadec-8-enyl]-6-methoxybenzoate
• CAS: 1314555-85-5
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: QNZNAWPANNKJMY-DOIQENQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (+)-2-hydroxy-6-(10'-hydroxypentadec-80(E)-enyl)benzoic acid 以 氯仿 为溶剂， 生成 (+)-2-methoxy-6-(10'-hydroxypentadec-80(E)-enyl)benzoic acid methyl ester
  参考文献：
  名称：

  New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights

  摘要：

  Bioassay-guided extraction of the stem bark of Knema laurina showed the acetylcholinesterase (AChE) inhibitory activity of DCM and hexane fractions. Further repeated column chromatography of hexane and DCM fractions resulted in the isolation and purification of five alkenyl phenol and salicylic acid derivatives. New compounds, (+)-2-hydroxy-6-(10'-hydroxypentadec-8'(E)-enyl)benzoic acid (1) and 3-pentadec-10'(Z)-enylphenol (2), along with known 3-heptadec-10'(Z)-enylphenol (3), 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid (4), and 2-hydroxy-6-(10'(Z)-heptadecenyl)benzoic acid (5) were isolated from the stem bark of this plant. Compounds (1-5) were tested for their acetylcholinesterase inhibitory activity. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and chemical derivatizations. Compound 5 showed strong acetylcholinesterase inhibitory activity with IC50 of 0.573 +/- 0.0260 mu M. Docking studies of compound 5 indicated that the phenolic compound with an elongated side chain could possibly penetrate deep into the active site of the enzyme and arrange itself through p-p interaction, H-bonding, and hydrophobic contacts with some critical residues along the complex geometry of the active gorge. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.065