N-(2,3-dihydroxypropyl)oleamide | 7336-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2,3-dihydroxypropyl)oleamide
• 英文别名: (Z)-N-(2,3-dihydroxypropyl)octadec-9-enamide
• CAS: 7336-22-3
• 化学式: C₂₁H₄₁NO₃
• 分子量: 355.561
• InChiKey: PPAJAKNTNIOXSS-KTKRTIGZSA-N

物化性质

• 沸点：
  546.8±50.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,3-dihydroxypropyl)oleamide 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 以75%的产率得到N-oleoyl glycinal
  参考文献：
  名称：

  Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals

  摘要：

  N-Arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.087
• 作为产物：
  描述：

  油酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-(2,3-dihydroxypropyl)oleamide
  参考文献：
  名称：

  OEA衍生物作为FAAH抑制剂的设计，合成和CoMFA研究

  摘要：

  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）。

  DOI：

  10.1007/s00044-017-1995-6

文献信息

• Osteoblast-specific mitogens and drugs containing such compounds
  申请人：Roche Diagnostics GmbH

  公开号：US06197759B1

  公开（公告）日：2001-03-06

  Osteoblast-specific mitogens and drugs containing such compounds can be used for treating metabolic bone diseases. These compounds include lysophosphatidylic acid derivatives selected from the group consisting of compounds of formula: wherein R1=alkenyl or alkynyl having from 6 to 24 carbon atoms; n=0-12; X=oxygen or NH; the compounds (all-cis-5,8,11,14)-eicosatetraenoic acid 2-hydroxy-3-phosphonooxypropyl ester; cis-9, cis-12-octadecadienoic acid 2-hydroxy-3-phosphonooxypropyl ester; (all-cis-9,12,15)-octadecatrienoic acid 2-hydroxy-3-phosphonooxypropyl ester; cis-9-octadecenoic acid 2-hydroxy-3-phosphonooxypropyl ester; and erucic acid 2-hydroxy-3-phosphonooxypropylester being excluded, and the physiologically tolerable salts, esters, optically active forms, and racemates of said compounds, and derivatives of said compounds, salts, esters, optically active forms and racemates which can be metabolized in vivo to yield the corresponding compound of formula (I).

  骨母细胞特异性促分裂因子和含有这类化合物的药物可用于治疗代谢性骨疾病。这些化合物包括从以下化合物组合中选择的溶磷脂酸衍生物：其中 R1=具有6至24个碳原子的烯基或炔基；n=0-12；X=氧或NH；所述化合物为（全顺-5,8,11,14）-二十碳四烯酸2-羟基-3-磷酸氧丙基酯；顺-9，顺-12-十八碳二烯酸2-羟基-3-磷酸氧丙基酯；（全顺-9,12,15）-十八碳三烯酸2-羟基-3-磷酸氧丙基酯；顺-9-十八碳烯酸2-羟基-3-磷酸氧丙基酯；和二十二碳二烯酸2-羟基-3-磷酸氧丙基酯被排除，以及所述化合物、盐、酯、光学活性形式和外消旋体的生理耐受盐、酯、光学活性形式和外消旋体的衍生物，这些衍生物可以在体内代谢产生相应的化合物（I）的衍生物。
• Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor
  作者：Florian Le Joubioux、Nicolas Bridiau、Mehdi Sanekli、Marianne Graber、Thierry Maugard

  DOI：10.1016/j.molcatb.2014.08.022

  日期：2014.11

  a two-step continuous enzymatic process with immobilized Candida antarctica lipase B (Novozym® 435) in a packed-bed bioreactor. The first step involved the selective N-acylation of 3-amino-1,2-propanediol using stearic acid as the first acyl donor (i). This was followed by the selective O-acylation of the N-stearyl 3-amino-1,2-propanediol synthesized in the first step, with myristic acid as the second

  神经酰胺是鞘脂化合物，在制药和化妆品工业中作为活性成分都非常有吸引力。在这项研究中，神经酰胺类似物的合成，即所谓的伪神经酰胺，进行了使用首次与固定的两步连续酶促过程念珠菌antarcti CA脂肪酶B（诺维信®在填充床435）生物反应器。第一步涉及使用硬脂酸作为第一酰基供体（i）对3-氨基-1，2-丙二醇进行选择性N-酰化。随后是第一步中合成的N-硬脂基3-氨基-1,2-丙二醇的选择性O-酰化反应，以肉豆蔻酸作为第二个酰基供体，生成N，O-二酰基3-氨基-1，2-丙二醇型假神经酰胺，即1- O-肉豆蔻基，3- N-硬脂基3-氨基-1，2-丙二醇（ii）。首先通过评估三个因素的影响对工艺进行优化：进料流速，生物催化剂的量和底物浓度。在最佳条件下，酰胺合成产率为92％，令人满意的生产率为3.15 mmol h -1  g生物催化剂-1（1128 mg h -1  g生物催化剂-1）。第二步，N-酰基3-氨基-1
• Neue Osteoblastenspezifische Mitogene: Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：Roche Diagnostics GmbH

  公开号：EP0906759A1

  公开（公告）日：1999-04-07

  Gegenstand der Erfindung sind Verbindungen der Formel (I) in der R1 = Alkyl, Alkenyl oder Alkinyl mit 6 bis 24 Kohlenstoffatomen, n = 0 - 12 X = Sauerstoff oder NH bedeuten sowie deren pharmakologisch unbedenkliche Salze, Ester, optisch aktive Formen, Racemate sowie Derivate, die in vivo zu Verbindungen der allgemeinen Fromel I metabolisiert werden können, Verfahren zu ihrer Herstellung, sowie Arzneimittel, die diese Verbindungen enthalten, zur Behandlung von Knochenstoffwechselstörungen.

  本发明的主题是式（I）化合物 其中 R1 = 具有 6 至 24 个碳原子的烷基、烯基或炔基、 n = 0 - 12 X = 氧或 NH 及其药理上可接受的盐、酯、光学活性形式、外消旋体和可在体内代谢为通式 I 化合物的衍生物、其制备工艺以及含有这些化合物的用于治疗骨代谢紊乱的药物。
• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
  作者：Hung The Dang、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Jae Sue Choi、Hyung Sik Kim、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2010.12.046

  日期：2011.2

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.