N-(4-methoxyphenethyl)palmitamide | 1215069-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxyphenethyl)palmitamide
• 英文别名: N-[2-(4-methoxyphenyl)ethyl]hexadecanamide
• CAS: 1215069-18-3
• 化学式: C₂₅H₄₃NO₂
• 分子量: 389.622
• InChiKey: UHXGQQUBPAHVHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-甲氧苯基)乙胺 、 棕榈酰氯 在 sodium carbonate 作用下， 以 甲苯 为溶剂， 生成 N-(4-methoxyphenethyl)palmitamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase

  摘要：

  N-Acylethanolamines, including N-palmitoyl-ethanolamine (PEA), are hydrolyzed to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH). Recently, N-acylethanolamine-hydrolyzing acid amidase (NAAA) was identified as being able to specifically hydrolyze PEA. In order to find selective and effective inhibitors of this enzyme, we synthesized and screened several amides, retroamides, esters, retroesters and carbamates of palmitic acid (1-21) and esters with C15 and C17 alkyl chains (22-27). Cyclopentylhexadecanoate (13) exhibited the highest inhibitory activity on NAAA (IC50 = 10.0 mu M), without inhibiting FAAH up to 50 mu M. Compound 13 may become a useful template to design new NAAA inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.134

文献信息

• Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase
  作者：Carmela Saturnino、Stefania Petrosino、Alessia Ligresti、Chiara Palladino、Giovanni De Martino、Tiziana Bisogno、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2009.11.134

  日期：2010.2

  N-Acylethanolamines, including N-palmitoyl-ethanolamine (PEA), are hydrolyzed to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH). Recently, N-acylethanolamine-hydrolyzing acid amidase (NAAA) was identified as being able to specifically hydrolyze PEA. In order to find selective and effective inhibitors of this enzyme, we synthesized and screened several amides, retroamides, esters, retroesters and carbamates of palmitic acid (1-21) and esters with C15 and C17 alkyl chains (22-27). Cyclopentylhexadecanoate (13) exhibited the highest inhibitory activity on NAAA (IC50 = 10.0 mu M), without inhibiting FAAH up to 50 mu M. Compound 13 may become a useful template to design new NAAA inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.