N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamide
• 英文别名: (5Z,8Z,11Z,14Z)-N-[(1S,2R)-2,3-dihydroxy-1-phenylpropyl]icosa-5,8,11,14-tetraenamide
• 化学式: C₂₉H₄₃NO₃
• 分子量: 453.665
• InChiKey: IGSDEXMOHOLNIQ-BQYFFGMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamide
  参考文献：
  名称：

  Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamides and evaluation of their anti-inflammatory activity

  摘要：

  Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamides and evaluate their analgesic and anti-inflammatory potential.Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Delta(13,14)-PGJ(2) (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1. 0.3, 1.0.3.0 and 10 mu M concentrations of the compounds.Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis).Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2012.06.040