Hexadecanoic acid (4-chloro-phenyl)-amide | 100172-16-5

• 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: Hexadecanoic acid (4-chloro-phenyl)-amide
• 英文别名: N-(4-chlorophenyl)hexadecanamide
• CAS: 100172-16-5
• 化学式: C₂₂H₃₆ClNO
• 分子量: 365.987
• InChiKey: OVRHPHDYSKENNR-UHFFFAOYSA-N

物化性质

• 沸点：
  501.3±33.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对氯苯胺 、 棕榈酰氯 以 二氯甲烷 为溶剂， 以50%的产率得到Hexadecanoic acid (4-chloro-phenyl)-amide
  参考文献：
  名称：

  Modifications of the Ethanolamine Head in N-Palmitoylethanolamine:  Synthesis and Evaluation of New Agents Interfering with the Metabolism of Anandamide

  摘要：

  The endogenous fatty acid amide anandamide (AEA) has, as a result of its actions on cannabinoid and vanilloid receptors, a number of important pharmacological properties including effects on nociception, memory processes, spasticity, and cell proliferation. Inhibition of the metabolism of AEA, catalyzed by fatty acid amide hydrolase (FAAH), potentiates the actions of AEA in vivo and therefore may be a useful target for drug development. In the present study, we have investigated whether substitution of the headgroup of the endogenous alternative FAAH substrate palmitoylethanolamide (PEA) can result in the identification of novel compounds preventing AEA metabolism. Thirty-seven derivatives of PEA were synthesized, with the C16 long chain of palmitic acid kept intact, and comprising 20 alkylated, 12 aromatic, and 4 halogenated amides. The ability of the PEA derivatives to inhibit FAAH-catalyzed hydrolysis of [H-3]AEA was investigated using rat brain homogenates as a source of FAAH. Inhibition curves were analyzed to determine the potency of the inhibitable fraction (pI(50) values) and the maximal attained inhibition for the compound, given that solubility in an aqueous environment is a major issue for these compounds. In the alkylamide family, palmitoylethyl-amide and palmitoylallylamide were inhibitors of AEA metabolism with PI50 values of 5.45 and 5.47, respectively. Halogenated derivatives (Cl and Br) exhibit PI50 values of similar to5.5 but rather low percentages of maximal inhibition. The -OH group of the ethyl head chain of N-palmitoylethanolamine was not necessary for interaction with FAAH. Amides containing aromatic moieties were less potent inhibitors of AEA metabolism. Compounds containing amide and ester bonds, 13 and 37, showed PI50 values of 4.99 and 5.08, respectively. None of the compounds showed obvious affinity for CB1 or CB2 receptors expressed on Chinese hamster ovary (CHO) cells. It is concluded that although none of the compounds were dramatically more potent than PEA itself at reducing the metabolism of AEA, the lack of effect of the compounds at CB1 and CB2 receptors makes them useful templates for development of possible therapeutic FAAH inhibitors.

  DOI：

  10.1021/jm0209679