3-methoxypentadec-(10'(Z)-enyl)benzene | 1314555-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxypentadec-(10'(Z)-enyl)benzene
• 英文别名: 1-methoxy-3-[(Z)-pentadec-10-enyl]benzene
• CAS: 1314555-86-6
• 化学式: C₂₂H₃₆O
• 分子量: 316.527
• InChiKey: WIWRMTXKBRXVSX-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 3-(pentadecen-10'(Z)-yl)phenol 以 乙醚 为溶剂， 生成 3-methoxypentadec-(10'(Z)-enyl)benzene
  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

文献信息

• New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights
  作者：Muhammad Nadeem Akhtar、Kok Wai Lam、Faridah Abas、Maulidiani、Syahida Ahmad、Syed Adnan Ali Shah、Atta-ur-Rahman、M. Iqbal Choudhary、Nordin Hj Lajis

  DOI：10.1016/j.bmcl.2011.04.065

  日期：2011.7

  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.