2-O-arachidonoylglyceryl ether | 57302-98-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-arachidonoylglyceryl ether
• 英文别名: 2-arachidonyl glycerol ether；1-O-arachidonylglycerol；1-arachidonylglycerol；noladin ether；3-eicosa-5c,8c,11c,14c-tetraenyloxy-propane-1,2-diol；1-O-Arachidonyl-glycerin；HU-310；3-[((8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenyl)oxy]-propane-1,2-diol；3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoxy]propane-1,2-diol
• CAS: 57302-98-4
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: MHROLVDNBHVTMB-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-eicosa-5c,8c,11c,14c-tetraenyloxymethyl-2,2-dimethyl-[1,3]dioxolane 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2-O-arachidonoylglyceryl ether
  参考文献：
  名称：

  抑制肾素活性的溶血磷脂酰乙醇胺类似物的合成。

  摘要：

  通过各自的脂肪醇的磷酸化和膦酰化反应，合成了一系列含有饱和的和亚甲基间断的顺式-烯烃脂肪链的溶血磷脂酰乙醇胺类似物。发现花生四烯酸基和亚麻基磷酰基乙醇胺（12、13），花生四烯酸基（2-邻苯二甲酰亚胺基乙基）膦酸酯（17）和花生四烯酸基（2-氨基乙基）膦酸酯（18）是体外肾素-肾素底物反应的有效抑制剂。较小的不饱和度的溶血磷脂酰乙醇胺类似物14-16是弱活性的或无活性的。在一项初步研究中，向高血压大鼠肌内注射25 mg / kg / day的花生四烯酸（2-氨基乙基）膦酸酯（18）可使血压在3天内显着降低（50 mm）；连续服用18天（15毫克/千克/天）再服用4天后，发现血浆肾素活性为16 ng / 0.1 ml / 15 hr，而最初给药前为69 ng / 0.1 ml / 15 hr。发现花生四烯酸（3），花生四烯醇（8）和几种相应的不是磷酸酯或膦酸酯的四烯酸酯，酰胺，甲磺酸酯和甘油

  DOI：

  10.1021/jm00246a003

文献信息

• Inhibitors of fatty acid amide hydrolase
  申请人：Boger L Dale

  公开号：US20060111359A1

  公开（公告）日：2006-05-25

  Improved competitive inhibitors of FAAH employ an α-keto heterocyclic pharmacophore and a binding subunit having a ?-unsaturation. The α-keto heterocyclic pharmacophore and a binding subunit are attached to one another, preferably by a hydrocarbon chain. The improvement lies in the use of a heterocyclic pharmacophore selected from oxazoles, oxadiazoles, thiazoles, and thiadiazoles that have alkyl or aryl substituents at their 4 and/or 5 positions. The improved competitive inhibitors of FAAH display enhanced activity over conventional competitive inhibitors of FAAH.

  改进的FAAH竞争性抑制剂采用α-酮杂环药基和具有?-不饱和度的结合亚单位。α-酮杂环药基和结合亚单位相互连接，最好通过一个碳氢链。改进之处在于使用从噁唑、噁二唑、噻唑和噻二唑中选择的具有烷基或芳基取代基的杂环药基，其在其4和/或5位置。改进的FAAH竞争性抑制剂显示出比传统FAAH竞争性抑制剂更强的活性。
• INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Boger Dale L.

  公开号：US20090270421A1

  公开（公告）日：2009-10-29

  Potent inhibitors of fatty acid amide hydrolase (FAAH) are constructed having K i 's below 200 pM and activities 10 2 -10 3 times more potent than the corresponding trifluoromethyl ketones. The potent inhibitors combine several features, viz.: 1.) an α-keto heterocylic head group; 2.) a hydrocarbon linkage unit employing an optimal C12-C8 chain length; and 3.) a phenyl or other π-unsaturation corresponding to the arachidonyl Δ 8,9 /Δ 11,12 and/or oleyl Δ 9,10 positions. A preferred α-keto heterocylic head group is α-keto N4 oxazolopyridine, with incorporation of a second weakly basic nitrogen. Fatty acid amide hydrolase is an enzyme responsible for the degradation of oleamide (an endogenous sleep-inducing lipid) and anandamide (an endogenous ligand for cannabinoid receptors).

  具有Ki值低于200 pM的脂肪酸酰胺水解酶（FAAH）的强效抑制剂被构建出来，其活性比相应的三氟甲基酮高102-103倍。这些强效抑制剂结合了几个特征，即：1）α-酮杂环头基团；2）使用最佳C12-C8链长的烃链连接单元；和3）与花生四烯酸Δ8,9/Δ11,12和/或油酸Δ9,10位置相对应的苯基或其他π-不饱和度。首选的α-酮杂环头基团是α-酮N4噁唑吡啶，并结合第二个弱碱性氮。脂肪酸酰胺水解酶是一种酶，负责降解油酰胺（一种内源性诱导睡眠的脂质）和阿那达胺（一种内源性的大麻素受体配体）。
• Hair and/or scalp treatment compositions
  申请人：Unilever PLC

  公开号：EP1785130A2

  公开（公告）日：2007-05-16

  Hair and/or scalp treatment compositions comprise an antidandruff agent, an effective amount of a cannabinoid receptor (CBR) activating agent and a cosmetically acceptable diluent or carrier. Alternatively, the compositions may be shampoo compositions comprising from 3 to 50 wt% surfactant, a CB receptor activating agent and a cosmetically acceptable diluent or carrier, provided that the CB receptor activating agent is not palmitoylethanolamide. The compositions are useful in the treatment and/or prevention of the symptoms of dandruff and can reduce scalp itch, a symptom which is typically associated with dandruff.

  头发和/或头皮治疗组合物由去屑剂、有效量的大麻素受体（CBR）激活剂和化妆品可接受的稀释剂或载体组成。或者，这些组合物可以是洗发水组合物，包含 3 至 50 wt%的表面活性剂、CB 受体激活剂和化妆品上可接受的稀释剂或载体，前提是 CB 受体激活剂不是棕榈酰乙醇酰胺。这些组合物可用于治疗和/或预防头皮屑症状，并可减轻头皮瘙痒（头皮屑的典型症状）。
• Blood based biomarkers for diagnosing atherosclerotic coronary artery disease
  申请人：Global Genomics Group, LLC

  公开号：US10254272B2

  公开（公告）日：2019-04-09

  The invention, in some aspects, relates to methods for evaluating a human subject for having atherosclerotic coronary artery disease (ASCAD) or as having a coronary atherosclerotic plaque. In some aspects, the invention relates to methods and kits useful for diagnosing, classifying, profiling and treating atherosclerotic CAD and or a coronary atherosclerotic plaque.

  在某些方面，本发明涉及评估人体是否患有冠状动脉粥样硬化性疾病（ASCAD）或冠状动脉粥样硬化斑块的方法。在某些方面，本发明涉及用于诊断、分类、剖析和治疗动脉粥样硬化性冠状动脉疾病和或冠状动脉粥样硬化斑块的方法和试剂盒。
• Orally administrable formulation
  申请人：Greenspoon Allen

  公开号：US10456357B2

  公开（公告）日：2019-10-29

  An orally administrable chewing gum formulation is provided comprising a pharmaceutically acceptable gum base and particles of a pharmaceutical agent ranging in size from about 50 to about 2000 μm, wherein the formulation comprises about 0.5-30% by wt of the pharmaceutical agent particles. A liquid formulation comprising particles of a pharmaceutical agent is also provided.

  本发明提供了一种可口服的口香糖配方，包括药学上可接受的口香糖基质和粒径在约 50 至约 2000 μm 之间的药剂颗粒，其中该配方包含约 0.5-30% （重量百分比）的药剂颗粒。还提供了一种包含药剂颗粒的液体制剂。