arachidonylamine | 194659-91-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: arachidonylamine
• 英文别名: Arachidonyl amine；(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-amine
• CAS: 194659-91-1
• 化学式: C₂₀H₃₅N
• 分子量: 289.505
• InChiKey: OOXRAGYSSZWMAE-DOFZRALJSA-N

物化性质

• 沸点：
  397.0±31.0 °C(Predicted)
• 密度：
  0.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  arachidonylamine 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 N-(2-hydroxymethyl-3-hydroxy-propanoyl)arachidonylamide
  参考文献：
  名称：

  Synthesis, cannabinoid receptor activity, and enzymatic stability of reversed amide derivatives of arachidonoyl ethanolamide

  摘要：

  Retroanandamide (2f) and its 10 analogues (la-e, 2a-e) were synthesized and evaluated for the cannabinoid receptor activation by a [S-35]GTP gamma S binding assay using rat cerebellar membranes, and Chinese hamster ovary cell membranes expressing human CB2 receptors. The primary goal of the study was to develop cannabinoid receptor agonists having improved enzymatic stability compared to endogenous N-arachidonoyl ethanolamide (AEA). Furthermore, by reversing the amide bond of AEA, the formation of arachidonic acid would be prevented. Finally, an effect of the carbonyl carbon position on the cannabinoid receptor activity was explored by synthesizing retroanandamide analogues having different chain lengths (la-e, C-19; 2a-f, C-20). All the synthesized compounds, except 2c, behaved as partial agonists for the both cannabinoid receptors. In rat brain homogenate, the reversed amides possessed significantly higher stability against FAAH induced degradation than AEA. Therefore, the reversed amide analogues of AEA may serve as enzymatically stable structural basis for the drug design based on the endogenous cannabinoids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.051
• 作为产物：
  描述：

  花生四烯酸 在 吡啶 、 lithium aluminium tetrahydride 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 arachidonylamine
  参考文献：
  名称：

  [EN] METHODS FOR MODULATING IKS CHANNEL ACTIVITY
  [FR] PROCÉDÉS PERMETTANT DE MODULER L'ACTIVITÉ DES CANAUX IKS

  摘要：

  公开号：

  WO2016022567A3

文献信息

• Cannabimimetic lipid amides as useful medications
  申请人：University of Connecticut

  公开号：US07161016B1

  公开（公告）日：2007-01-09

  Novel analogs of arachidonylethanolamide are presented which have higher affinities for the cannabinoid CB1 and/or CB2 receptor sites. Further, most of the analogs exhibit greater metabolic stability than arachidonylethanolamide. The improved receptor affinity and selectivity and/or greater metabolic stability make these analogs therapeutically useful as medications for relief of pain caused by cancer and nausea caused by chemotherapy, as well as for peripheral pain. The compounds may also be useful as oral and topical contraceptives, in suppression of the immune system, enhancement of appetite and in treatment of psychomotor disorders, multiple sclerosis and hypertension.

  新型的花生四烯酰乙醇胺类似物具有更高的亲和力，适用于大麻素CB1和/或CB2受体位点。此外，大多数类似物表现出比花生四烯酰乙醇胺更高的代谢稳定性。改善的受体亲和力和选择性和/或更高的代谢稳定性使这些类似物在作为药物用于缓解癌症引起的疼痛和化疗引起的恶心，以及外周疼痛方面具有治疗用途。这些化合物也可能用于口服和局部避孕药、免疫系统抑制、增强食欲以及治疗精神运动障碍、多发性硬化和高血压。
• ABUSE DETERRENT AND ANTI-DOSE DUMPING PHARMACEUTICAL SALTS USEFUL FOR THE TREATMENT OF ATTENTION DEFICIT/HYPERACTIVITY DISORDER
  申请人：King Clifford Riley

  公开号：US20120028960A1

  公开（公告）日：2012-02-02

  A pharmaceutical composition comprising a drug substance consisting essentially of a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound wherein the amine containing pharmaceutical active compound is selected from the group consisting of racemic or single isomer ritalinic acid or phenethylamine derivatives and the drug substance has a physical form selected from amorphous and polymorphic.

  一种药物组合物，包括基本上由含有药用活性化合物的胺的药用可接受的有机酸加合盐组成的药物物质，其中含有药用活性化合物的胺被选择自光学异构体或单异构体利他林酸或苯乙胺衍生物的群体，并且该药物物质具有从无定形到多型的物理形式。
• Synthesis and pharmacological evaluation of sulfamide-based analogues of anandamide
  作者：Carolina Cano、Juan Antonio Páez、Pilar Goya、Antonia Serrano、Javier Pavón、Fernando Rodríguez de Fonseca、Margarita Suardíaz、María Isabel Martín

  DOI：10.1016/j.ejmech.2009.08.003

  日期：2009.12

  Arachidonyl and linoleyl sulfamide derivatives have been synthesized and their potential cannabimimetic properties evaluated in in vitro functional and binding assays. Replacement of the ethanolamide moiety of anandamide by –CH2NHSO2NH–R considerably reduces the CB1 receptor activity and only some of the compounds showed modest cannabinoid properties in binding assays. The new compounds were also tested

  已经合成了花生四烯酸和亚油基磺酰胺衍生物，并在体外功能和结合试验中评估了它们的潜在拟大麻特性。-CH 2 NHSO 2 NH-R取代an南酰胺的乙醇酰胺部分会大大降低CB1受体的活性，只有一些化合物在结合分析中显示适度的大麻素特性。还测试了新化合物作为FAAH酶的抑制剂，但没有活性。
• Synthesis of COX-2 and FAAH inhibitors
  申请人：Bartolini Wilmin

  公开号：US20050234244A1

  公开（公告）日：2005-10-20

  Methods for preparing indoles that are useful COX-2 inhibitors and intermediates useful in such methods are described.

  描述了制备对COX-2抑制剂有用的吲哚和在这些方法中有用的中间体的方法。
• Bisarylimidazolyl fatty acid amide hydrolase inhibitors
  申请人：——

  公开号：US20020188009A1

  公开（公告）日：2002-12-12

  The present invention relates to bisarylimidazolyl derivatives and pharmaceutical compositions comprising said compounds inhibiting fatty acid amide hydrolase and useful for the treatment of pain, particularly neuropathic pain, psychomotor disorder, hypertension, cardiovascular disease, eating disorder, nausea, AIDS-related complex, glaucoma, inflammation, psoriasis or multiple sclerosis, and other conditions the treatment of which can be effected by inhibiting fatty acid amide hydrolase.

  本发明涉及双芳基咪唑基衍生物和含有该类化合物的药物组合物，该组合物能抑制脂肪酸酰胺水解酶，适用于治疗疼痛，特别是神经病性疼痛、精神运动障碍、高血压、心血管疾病、进食障碍、恶心、艾滋病相关综合症、青光眼、炎症、牛皮癣或多发性硬化等疾病，以及其他通过抑制脂肪酸酰胺水解酶可治疗的疾病。