N-(2-氯乙基)棕榈酰胺 | 524705-63-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-(2-氯乙基)棕榈酰胺
• 英文名称: N-(2-chloroethyl)-hexadecanamide
• 英文别名: N-(2-Chloroethyl)Palmitamide；N-(2-chloroethyl)hexadecanamide
• CAS: 524705-63-3
• 化学式: C₁₈H₃₆ClNO
• 分子量: 317.943
• InChiKey: YUWQWGFCGCKQFY-UHFFFAOYSA-N

物化性质

• 沸点：
  448.9±28.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-氯乙基)棕榈酰胺 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-pentadecyl-2-oxazoline
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES
  [FR] COMPOSITIONS ET PROCÉDÉS POUR LA MODULATION D'AMIDASES SPÉCIFIQUES POUR DES N-ACYLÉTHANOLAMINES EN VUE D'UNE UTILISATION DANS LA THÉRAPIE CONTRE LES MALADIES INFLAMMATOIRES

  摘要：

  公开号：

  WO2013121449A8
• 作为产物：
  描述：

  十六酰胺乙醇 在 氯化亚砜 作用下， 反应 15.5h， 生成 N-(2-氯乙基)棕榈酰胺
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES
  [FR] COMPOSITIONS ET PROCÉDÉS POUR LA MODULATION D'AMIDASES SPÉCIFIQUES POUR DES N-ACYLÉTHANOLAMINES EN VUE D'UNE UTILISATION DANS LA THÉRAPIE CONTRE LES MALADIES INFLAMMATOIRES

  摘要：

  公开号：

  WO2013121449A8

文献信息

• Soft Antimicrobial Agents:  Synthesis and Activity of Labile Environmentally Friendly Long Chain Quaternary Ammonium Compounds
  作者：Thorsteinn Thorsteinsson、Már Másson、Karl G. Kristinsson、Martha A. Hjálmarsdóttir、Hilmar Hilmarsson、Thorsteinn Loftsson

  DOI：10.1021/jm030829z

  日期：2003.9.1

  A series of soft quaternary ammonium antimicrobial agents, which are analogues to currently used quaternary ammonium preservatives such as cetyl pyridinium chloride and benzalkonium chloride, were synthesized. These soft analogues consist of long alkyl chain connected to a polar headgroup via chemically labile spacer group. They are characterized by facile nonenzymatic and enzymatic degradation to form their original nontoxic building blocks. However, their chemical stability has to be adequate in order for them to have antimicrobial effects. Stability studies and antibacterial and antiviral activity measurements revealed relationship between activity, lipophilicity, and stability. Their minimum inhibitory concentration (MIC) was as low as 1 mug/mL, and their viral reduction was in some cases greater than 6.7 log. The structure -activity studies demonstrate that the bioactive compounds (i.e., MIC for Gram-positive bacteria of < 10 umug/mL) have an alkyl chain length between 12 and 18 carbon atoms, with a polar headgroup preferably of a small quaternary ammonium group, and their acquired inactivation half-life must be greater than 3 h at 60 degreesC.
• Modifications of the Ethanolamine Head in <i>N</i>-Palmitoylethanolamine:  Synthesis and Evaluation of New Agents Interfering with the Metabolism of Anandamide
  作者：Séverine Vandevoorde、Kent-Olov Jonsson、Christopher J. Fowler、Didier M. Lambert

  DOI：10.1021/jm0209679

  日期：2003.4.1

  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.
• Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
  作者：Hung The Dang、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Jae Sue Choi、Hyung Sik Kim、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2010.12.046

  日期：2011.2

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.