N-oleylethanolamine | 162758-96-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-oleylethanolamine
• 英文别名: N-(2-Hydroxyethyl)-9-octadecenamide；N-(2-hydroxy-ethyl)-elaidamide；N-(2-Hydroxy-aethyl)-elaidamid；Elaidinsaeure-(2-hydroxy-aethylamid)；N-(2-Hydroxy-aethyl)-elaidinamid；elaidylethanolamide；(E)-N-(2-hydroxyethyl)octadec-9-enamide
• CAS: 162758-96-5
• 化学式: C₂₀H₃₉NO₂
• 分子量: 325.535
• InChiKey: BOWVQLFMWHZBEF-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  反油酸 、 C.I.酸性橙108 生成 N-oleylethanolamine
  参考文献：
  名称：

  Swern; Stutzman; Roe, Journal of the American Chemical Society, 1949, vol. 71, p. 3018

  摘要：

  DOI：

文献信息

• Synthesis and Anticonvulsant Activity of<i>N</i>-(2-Hydroxy-ethyl)amide Derivatives
  作者：Li-Ping Guan、Dong-Hai Zhao、Jing-Hui Xiu、Xin Sui、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1002/ardp.200800153

  日期：2009.1

  N‐(2‐hydroxyethyl)amide derivatives was synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, and their neurotoxicity was evaluated by the rotarod test (Tox). The maximal electroshock test showed that N‐(2‐hydroxyethyl)decanamide 1g, N‐(2‐hydroxyethyl)palmitamide 1l, and N‐(2‐hydroxyeth‐yl)stearamide 1n were found to show a better anticonvulsant activity and also had

  合成了一系列新型 N-(2-羟乙基)酰胺衍生物，并通过最大电休克 (MES) 试验筛选其抗惊厥活性，并通过旋转棒试验 (Tox) 评估其神经毒性。最大电休克试验表明，N-（2-羟乙基）癸酰胺 1g、N-（2-羟乙基）棕榈酰胺 1l 和 N-（2-羟乙基）硬脂酰胺 1n 显示出更好的抗惊厥活性，并且具有更低的抗惊厥活性。毒性比标记的抗癫痫药丙戊酸盐要低。在抗 MES 效力测试中，这些化合物的中位有效剂量 (ED50) 分别为 22.0、23.3、20.5 mg/kg，中位毒性剂量 (TD50) 分别为 599.8、>1000、>1000 mg/kg，导致保护指数 (PI) 分别为 27.5、>42.9、>48.8。这是比标记的抗癫痫药物丙戊酸盐（PI = 1.6）更好的保护指数。为了进一步研究几种不同模型中抗惊厥活性的影响，测试了化合物 1g、1l 和 1n 引起的惊厥，这些化学物质包括戊四
• Pharmacological Characterization of Hydrolysis-Resistant Analogs of Oleoylethanolamide with Potent Anorexiant Properties
  作者：Giuseppe Astarita、Barbara Di Giacomo、Silvana Gaetani、Fariba Oveisi、Timothy R. Compton、Silvia Rivara、Giorgio Tarzia、Marco Mor、Daniele Piomelli

  DOI：10.1124/jpet.106.105221

  日期：2006.8

  Oleoylethanolamide (OEA) is an endogenous lipid mediator that reduces food intake, promotes lipolysis, and decreases body weight gain in rodents by activating peroxisome proliferator-activated receptor-α (PPAR-α). The biological effects of OEA are terminated by two intracellular lipid hydrolase enzymes, fatty-acid amide hydrolase and N -acylethanolamine-hydrolyzing acid amidase. In the present study, we describe OEA analogs that resist enzymatic hydrolysis, activate PPAR-α with high potency in vitro, and persistently reduce feeding when administered in vivo either parenterally or orally. The most potent of these compounds, ( Z )-( R )-9-octadecenamide, N -(2-hydroxyethyl,1-methyl) (KDS-5104), stimulates transcriptional activity of PPAR-α with a half-maximal effective concentration (EC50) of 100 ± 21 nM ( n = 11). Parenteral administration of KDS-5104 in rats produces persistent dose-dependent prolongation of feeding latency and postmeal interval (half-maximal effective dose, ED50 = 2.4 ± 1.8 mg kg-1 i.p.; n = 18), as well as increased and protracted tissue exposure compared with OEA. Oral administration of the compound also results in a significant tissue exposure and reduction of food intake in free-feeding rats. These results suggest that the endogenous high-affinity PPAR-α agonist OEA may provide a scaffold for the discovery of novel orally active PPAR-α ligands.

  油酰乙醇酰胺（OEA）是一种内源性脂质介质，可通过激活过氧化物酶体增殖激活受体-α（PPAR-α）来降低啮齿动物的食物摄入量、促进脂肪分解并减少体重增加。OEA 的生物效应由两种细胞内脂质水解酶（脂肪酸酰胺水解酶和 N -酰基乙醇胺水解酸酰胺酶）终止。在本研究中，我们描述了能抵抗酶水解的 OEA 类似物，它们能在体外高效力地激活 PPAR-α，并在体内经肠道或口服给药后持续减少摄食。这些化合物中效力最强的是 ( Z )-( R )-9- 十八烯酰胺，N -（2-羟乙基，1-甲基）（KDS-5104），它能刺激 PPAR-α 的转录活性，其半最大有效浓度（EC50）为 100 ± 21 nM（n = 11）。与 OEA 相比，KDS-5104 给大鼠肠外给药会产生持续的剂量依赖性进食潜伏期和餐后间隔延长（半数最大有效剂量，ED50 = 2.4 ± 1.8 mg kg-1 i.p.；n = 18），以及组织暴露增加和延长。在自由采食的大鼠中，口服该化合物也会导致显著的组织暴露和食物摄入量减少。这些结果表明，内源性高亲和力 PPAR-α 激动剂 OEA 可为发现新型口服活性 PPAR-α 配体提供支架。
• Combination therapy for controlling appetites
  申请人：Piomelli Daniele

  公开号：US20050101542A1

  公开（公告）日：2005-05-12

  The invention provides methods and pharmaceutical compositions for administering a PPARα agonist (e.g., OEA-like agonist, OEA-like compound), an OEA-like appetite reducing compound, or a FAAH inhibitor and a CB1 cannabinoid receptor antagonist to a subject in order to reduce the consumption or ingestion of food, ethanol or other appetizing substances as well as in treating appetency disorders related to the excess consumption of food, ethanol, and other appetizing substances. The combination therapy can also be useful for reducing body fat or body weight and modulating lipid metabolism.

  该发明提供了一种方法和制药组合物，用于给予PPARα激动剂（例如，OEA样激动剂，OEA样化合物），OEA样食欲减少化合物，或FAAH抑制剂和CB1大麻素受体拮抗剂给予受试者，以减少食物、乙醇或其他开胃物质的摄入或摄入量，并治疗与过量摄入食物、乙醇和其他开胃物质相关的食欲紊乱。该联合治疗也可用于减少体脂肪或体重和调节脂质代谢。
• AMINE DERIVATIVE AND DERMATOLOGIC PREPARATION CONTAINING THE SAME
  申请人：Kao Corporation

  公开号：EP0691327A1

  公开（公告）日：1996-01-10

  An amine derivative of following general formula (I) or (II) (wherein R1 represents a heteroatom-containing C1-C40 hydrocarbon group which may have a ring structure, etc.; R2 to R6 each represent a C1-C10 hydrocarbon group, hydrogen, etc.; A1 represents (i) or R15-Z-R16(CH2)n-; B1 represents hydrogen, a C1-C10 hydrocarbon group, nitrogen, etc.; and C1 represents hydrogen, a C1-C10 hydrocarbon group, nitrogen, alcohol residue, phosphoric acid residue, etc.); a dermatologic preparation containing the same; and a process for producing the amine derivative. The amine derivative has excellent effects of smoothing wrinkles and improving keratodermia.

  以下通式(I)或(II)的胺衍生物（其中 R1 代表含杂原子的 C1-C40 烃基，可具有环状结构等；R2 至 R6 各代表 C1-C10 烃基、氢等；A1 代表(i)或 R15-Z-R16(CH2)n- ；B1 代表氢、C1-C10 烃基、氮等；C1 代表氢、C1-C10 烃基、氮等）。A1代表(i)或 R15-Z-R16(CH2)n-；B1代表氢、C1-C10 烃基、氮等；C1代表氢、C1-C10 烃基、氮、醇残留物、磷酸残留物等）；含有相同成分的皮肤病制剂；以及生产胺衍生物的工艺。胺衍生物在抚平皱纹和改善角质层方面具有卓越的效果。
• Methods for identification of modulators of OSGPR116 activity, and their use in the treatment of disease
  申请人：Griffin Graeme

  公开号：US20060199229A1

  公开（公告）日：2006-09-07

  This invention relates to the identification of fatty acid or lipid amides that decrease food intake in mammals, including fatty acid ethanolamides, as ligands for the G-protein coupled receptor OSGPR116, and describes the first demonstration of a specific G-protein coupled receptor that is activated by fatty acid ethanolamides that inhibit feeding. The invention is directed to new methods for screening candidate drugs for their ability to modulate the activity of OSGPR116, and new pharmaceutical agents identified by these methods. It is also directed to the use of such agents in the manufacture of medicaments for the treatment of OSGPR116 mediated diseases, and methods of treating diseases such as obesity and diabetes by administering to an individual a therapeutic amount of a modulator of OSGPR116 identified by these methods.

  本发明涉及鉴定可降低哺乳动物食物摄入量的脂肪酸或脂质酰胺，包括脂肪酸乙醇酰胺，作为 G 蛋白偶联受体 OSGPR116 的配体，并描述了首次证明一种特定的 G 蛋白偶联受体可被抑制摄食的脂肪酸乙醇酰胺激活。本发明涉及筛选候选药物以确定其调节 OSGPR116 活性能力的新方法，以及通过这些方法确定的新药剂。本发明还涉及使用这些制剂制造治疗 OSGPR116 介导的疾病的药物，以及通过向个体施用治疗量的通过这些方法鉴定的 OSGPR116 调节剂来治疗肥胖和糖尿病等疾病的方法。