3‐hydroxy‐N‐pentadecylpropanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3‐hydroxy‐N‐pentadecylpropanamide
• 英文别名: 3-Hydroxy-N-pentadecyl-propionamide；3-hydroxy-N-pentadecylpropanamide
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: SSLJHCZVZIBYMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-十五醇 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三甲基铝 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3‐hydroxy‐N‐pentadecylpropanamide
  参考文献：
  名称：

  Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of N-Palmitoylethanolamine- Selective Acid Amidase

  摘要：

  Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of "N-palmitoylethanolamine hydrolase" described so far. These compounds are devoid of affinity for CB, and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 muM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.

  DOI：

  10.1021/jm0340795

文献信息

• Synthesis, Molecular Modeling and Biological Evaluation of Metabolically Stable Analogues of the Endogenous Fatty Acid Amide Palmitoylethanolamide
  作者：Alessia D’Aloia、Federica Arrigoni、Renata Tisi、Alessandro Palmioli、Michela Ceriani、Valentina Artusa、Cristina Airoldi、Giuseppe Zampella、Barbara Costa、Laura Cipolla

  DOI：10.3390/ijms21239074

  日期：——

  efficacy and tolerability. However, the exogenously administered PEA is rapidly inactivated; in this process, fatty acid amide hydrolase (FAAH) plays a key role both in hepatic metabolism and in intracellular degradation. So, the aim of the present study was the design and synthesis of PEA analogues that are more resistant to FAAH-mediated hydrolysis. A small library of PEA analogues was designed and

  棕榈酰乙醇酰胺（PEA）属于N-酰基乙醇胺，是一种内源性脂质，可能在广泛的治疗领域中使用。含有PEA的产品具有止痛和抗炎特性，证明其功效和耐受性，被许可用于人体中的营养保健品，食品补充剂或医疗食品。但是，外源给药的PEA会迅速失活。在此过程中，脂肪酸酰胺水解酶（FAAH）在肝代谢和细胞内降解中均起着关键作用。因此，本研究的目的是设计和合成对FAAH介导的水解反应更具抗性的PEA类似物。设计了一个小的PEA类似物库，并通过分子对接和密度泛函理论计算进行了测试，以找到更稳定的类似物。通过计算研究，从合成可及性和对FAAH介导的水解的代谢稳定性方面来说，RePEA是最佳候选者。合成所选化合物并进行离体测定，以监测FAAH介导的水解并确认其抗炎特性。对包含在完整膜蛋白中的FAAH的膜样品进行的1 H-NMR光谱表明，与PEA相反，RePEA不被FAAH处理。此外，RePEA保留了PEA抑制鼠N9小
• Esters, Retroesters, and a Retroamide of Palmitic Acid: Pool for the First Selective Inhibitors of <i>N</i>-Palmitoylethanolamine- Selective Acid Amidase
  作者：Séverine Vandevoorde、Kazuhito Tsuboi、Natsuo Ueda、Kent-Olov Jonsson、Christopher J. Fowler、Didier M. Lambert

  DOI：10.1021/jm0340795

  日期：2003.10.1

  Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of "N-palmitoylethanolamine hydrolase" described so far. These compounds are devoid of affinity for CB, and CB2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 muM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.