N-(4-hydroxyphenethyl)oleamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxyphenethyl)oleamide
• 英文别名: (Z)-N-[2-(4-hydroxyphenyl)ethyl]octadec-9-enamide
• 化学式: C₂₆H₄₃NO₂
• 分子量: 401.633
• InChiKey: MWHSBABGQKDUFQ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  油酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-(4-hydroxyphenethyl)oleamide
  参考文献：
  名称：

  Synthesis and Evaluation of Fatty Acid Amides on the <i>N</i>-Oleoylethanolamide-Like Activation of Peroxisome Proliferator Activated Receptor α

  摘要：

  合成了一系列脂肪酸酰胺，并评估了它们在正常大鼠肝细胞系clone 9中对过氧化物酶体增殖物激活剂受体α（PPAR-α）的激动活性。通过实时反转录聚合酶链反应（RT-PCR）测定了PPAR-α下游基因肉碱棕榈酰转移酶-1和线粒体3-羟基-3-甲基戊二酰辅酶A合酶的mRNA，作为PPAR-α激动活性的指标。我们合成了九种油酸酰胺。它们的PPAR-α激动活性按递减顺序为N-油酸组胺（OLHA）、N-油酸甘氨酸、油酰胺、N-油酸酪胺、N-油酸血清素和Olvanil。最高活性出现在OLHA。我们还合成并评估了九种N-酰基组胺（N-acyl-HAs）。其中，OLHA、C16:0-HA和C18:1Δ9-trans-HA显示出相似的活性。由于饱和脂肪酸不同链长的活性在C16:0-HA处达到峰值。PPAR-α拮抗剂GW6471抑制了OLHA和N-油酸乙醇酰胺（OEA对PPAR-α下游基因的诱导。这些数据表明N-酰基组胺可以被视为新的PPAR-α激动剂。

  DOI：

  10.1248/cpb.c14-00881

文献信息

• Design, synthesis and CoMFA studies of OEA derivatives as FAAH inhibitors
  作者：Daxiong Han、Biyan Wang、Hui Jin、Haiyan Wang、Meimei Chen

  DOI：10.1007/s00044-017-1995-6

  日期：2017.11

  inhibitory activities against fatty acid amide hydrolase. Among of them, 13 compounds inhibit fatty acid amide hydrolase by 50% at the concentration of 100 μM. Of these compounds, the most active one is compound 9, which inhibit fatty acid amide hydrolase activity 98.35% at the concentration of 100 µM. Comparative molecular field analysis analyzes were performed based on obtained biological activities data

  总共设计，合成和表征了26种新颖的油酰基乙醇酰胺衍生物。筛选所有合成的目标化合物对脂肪酸酰胺水解酶的抑制活性。其中13种化合物在100μM的浓度下可抑制50％的脂肪酸​​酰胺水解酶。在这些化合物中，活性最高的是化合物9，当浓度为100 µM时，其抑制脂肪酸酰胺水解酶活性的比例为98.35％。根据获得的生物活性数据进行比较分子场分析，得出具有可靠预测能力的统计可靠的比较分子场分析模型（r 2  = 0.978，q 2  = 0.613）。
• Termitomycamides A to E, Fatty Acid Amides Isolated from the Mushroom <i>Termitomyces titanicus</i>, Suppress Endoplasmic Reticulum Stress
  作者：Jae-Hoon Choi、Kohei Maeda、Kaoru Nagai、Etsuko Harada、Mitsuo Kawade、Hirofumi Hirai、Hirokazu Kawagishi

  DOI：10.1021/ol102186p

  日期：2010.11.5

  Five fatty acid amides, termitomycamides A to E (1 to 5), were isolated from the giant edible mushroom Termitomyces titanicus. The structures of 1-5 were determined by the interpretation of spectral data and/or synthesis. Compounds 2 and 5 showed protective activity against endoplasmic reticulum stress-dependent cell death.
• Inhibitors of anthrax lethal factor
  作者：Brandon D. Gaddis、Larisa V. Avramova、Jean Chmielewski

  DOI：10.1016/j.bmcl.2007.05.089

  日期：2007.8

  An inhibitor of anthrax lethal toxin mediated cell death (1) was identified by a medium throughput cell-based screen. This compound was determined to specifically inhibit anthrax lethal factor (LF), and subsequent SAR studies produced an even more potent inhibitor (4). Mechanistic studies identified these agents as uncompetitive inhibitors of LF with K-i values of 3.0 and 1.7 mu M, respectively, with good cell potency and low cytotoxicity. (c) 2007 Elsevier Ltd. All rights reserved.
• Discovery of Novel Oleamide Analogues as Brain-Penetrant Positive Allosteric Serotonin 5-HT_2C Receptor and Dual 5-HT_2C/5-HT_2A Receptor Modulators
  作者：Jianping Chen、Erik J. Garcia、Christina R. Merritt、Joshua C. Zamora、Andrew A. Bolinger、Konrad Pazdrak、Susan J. Stafford、Randy C. Mifflin、Eric A. Wold、Christopher T. Wild、Haiying Chen、Noelle C. Anastasio、Kathryn A. Cunningham、Jia Zhou

  DOI：10.1021/acs.jmedchem.3c00908

  日期：2023.7.27
• HUMAN GUT MICROBIOME-DERIVED BIOSYNTHETIC ENZYMES FOR PRODUCTION OF FATTY ACID AMIDES
  申请人：Massachusetts Institute of Technology

  公开号：US20200299738A1

  公开（公告）日：2020-09-24

  Disclosed herein, in some embodiments, are vectors encoding biosynthetic enzymes from gut microbiome-derived bacterium (e.g., Clostridia enzymes), engineered cells comprising the vectors, and methods of using biosynthetic enzymes from gut microbiome-derived bacterium (e.g., Clostridia enzymes) to produce fatty acid amides.