1-O-palmitoleoyl-rac-glycidol

• 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: 1-O-palmitoleoyl-rac-glycidol
• 英文别名: Glycidyl Palmitoleate；oxiran-2-ylmethyl (Z)-hexadec-9-enoate
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: FWEHVPCBXKCYHE-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-palmitoleoyl-rac-glycidol 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.83h， 生成
  参考文献：
  名称：

  Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin

  摘要：

  The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.083
• 作为产物：
  描述：

  缩水甘油 、 palmitoleoyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-O-palmitoleoyl-rac-glycidol
  参考文献：
  名称：

  Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof

  摘要：

  该发明提供了抗凋亡组合物溶磷脂酸及其制备和使用方法。这种组合物还可以包含增强LPA作用的剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以额外含有其他药用有效剂，如药物、抗生素、伤口愈合剂和抗氧化剂。

  公开号：

  US06949528B1

文献信息

• Compositions containing lysophosphotidic acids which inhibit apoptosis and uses thereof
  申请人：Bathurst C. Ian

  公开号：US20060063738A1

  公开（公告）日：2006-03-23

  The present invention provides therapeutic compositions containing lysophosphatidic acids, methods for making the compositions, and methods of use thereof.

  本发明提供了含有溶血磷脂酸的治疗组合物，制备该组合物的方法以及使用该组合物的方法。
• COMPOSITIONS CONTAINING LYSOPHOSPHATIDIC ACIDS WHICH INHIBIT APOPTOSIS AND USES THEREOF
  申请人：Goddard G. John

  公开号：US20080076736A1

  公开（公告）日：2008-03-27

  The invention provides anti-apoptotic compositions containing lysophosphatidic acids and methods for making and using the compositions. Such compositions may also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.

  本发明提供了含有溶血磷脂酸的抗凋亡组合物及其制备和使用方法。这样的组合物还可以含有LPA增效剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以另外含有其他药效物质，如药物、抗生素、伤口愈合剂和抗氧化剂。
• Structure−Activity Relationship of a Series of Inhibitors of Monoacylglycerol HydrolysisComparison with Effects upon Fatty Acid Amide Hydrolase
  作者：José Antonio Cisneros、Séverine Vandevoorde、Silvia Ortega-Gutiérrez、Clément Paris、Christopher J. Fowler、María L. López-Rodríguez

  DOI：10.1021/jm070642y

  日期：2007.10.1

  A series of 32 heterocyclic analogues based on the structure of 2-arachidonoylglycerol (2-AG) were synthesized and tested for their ability to inhibit monoacylglycerol lipase and fatty acid an-tide hydrolase activities. The designed compounds feature a hydrophobic moiety and different heterocyclic subunits that mimic the glycerol fragment. This series has allowed us to carry out the first systematic structure activity relationship study on inhibition of 2-AG hydrolysis. The most promising compounds were oxiran-2-ylmethyl (5Z,8Z,l 11Z,14Z)-icosa-5,8,11,14-tetraenoate (1) and tetrahydro-2H-pyran-2-ylmethyl (5Z,8Z,11Z,14z)-icosa5,8,11,14-tetraenoate (5). They inhibited cytosolic 2-oleoylglycerol (2-OG) hydrolysis completely (IC50 values of 4.5 and 5.6 mu M, respectively). They also blocked, albeit less potently, 2-OG hydrolysis in membrane fractions (IC50 values of 19 and 26,mu M, respectively) and anandamide hydrolysis (IC50 values of 12 and 51 mu M, respectively). These compounds will be useful in delineating the importance of the cytosolic hydrolytic activity in the regulation of 2-AG levels and, hence, its potential as a target for drug development.
• US6495532B1
  申请人：——

  公开号：US6495532B1

  公开（公告）日：2002-12-17
• US6949529B2
  申请人：——

  公开号：US6949529B2

  公开（公告）日：2005-09-27