2-[12-(3-hydroxy-5-pentylphenoxy)dodecyloxy]propane-1,3-diol | 1350724-88-7

• 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-[12-(3-hydroxy-5-pentylphenoxy)dodecyloxy]propane-1,3-diol
• 英文别名: 2-[12-(3-Hydroxy-5-pentylphenoxy)dodecoxy]propane-1,3-diol
• CAS: 1350724-88-7
• 化学式: C₂₆H₄₆O₅
• 分子量: 438.648
• InChiKey: UFVVPGSIQDJDQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,12-二溴十二烷 在 盐酸 、 potassium fluoride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 52.0h， 生成 2-[12-(3-hydroxy-5-pentylphenoxy)dodecyloxy]propane-1,3-diol
  参考文献：
  名称：

  Resorcinol-sn-Glycerol Derivatives: Novel 2-Arachidonoylglycerol Mimetics Endowed with High Affinity and Selectivity for Cannabinoid Type 1 Receptor

  摘要：

  Since the discovery of the endocannabinoid system, evidence has been progressively accumulating to suggest that 2-arachidonoylglycerol (2-AG) rather than anandamide (AEA) is the endogenous ligand for both cannabinoid (CB) receptors. Moreover, other studies have shown that another lipid molecule, 2-arachidonyl-glycerol ether (2-AGE, noladin ether), which acts as a full agonist at cannabinoid receptors, might occur in tissues. Having previously designed a resorcinol AEA hybrid model, in this paper we have explored the cannabinoid receptor binding properties, the CB, functional activity, and the stability to plasma esterases of a novel series of compounds characterized by the conversion of the amide head into the glycerol-ester or glycerol-ether head, typical of 2-AG or the "putative" endocannabinoid 2-AGE, respectively. Glyceryl esters 39 and 41 displayed greater potency for CB, (K, in the nanomolar range) than for CB2 receptors plus the potential to be exploited as useful hits for the development of novel 2-AG mimetics.

  DOI：

  10.1021/jm200529h

文献信息

• Resorcinol-<i>sn</i>-Glycerol Derivatives: Novel 2-Arachidonoylglycerol Mimetics Endowed with High Affinity and Selectivity for Cannabinoid Type 1 Receptor
  作者：Antonella Brizzi、Maria Grazia Cascio、Maria Frosini、Alessia Ligresti、Francesca Aiello、Irene Biotti、Vittorio Brizzi、Roger Guy Pertwee、Federico Corelli、Vincenzo Di Marzo

  DOI：10.1021/jm200529h

  日期：2011.12.22

  Since the discovery of the endocannabinoid system, evidence has been progressively accumulating to suggest that 2-arachidonoylglycerol (2-AG) rather than anandamide (AEA) is the endogenous ligand for both cannabinoid (CB) receptors. Moreover, other studies have shown that another lipid molecule, 2-arachidonyl-glycerol ether (2-AGE, noladin ether), which acts as a full agonist at cannabinoid receptors, might occur in tissues. Having previously designed a resorcinol AEA hybrid model, in this paper we have explored the cannabinoid receptor binding properties, the CB, functional activity, and the stability to plasma esterases of a novel series of compounds characterized by the conversion of the amide head into the glycerol-ester or glycerol-ether head, typical of 2-AG or the "putative" endocannabinoid 2-AGE, respectively. Glyceryl esters 39 and 41 displayed greater potency for CB, (K, in the nanomolar range) than for CB2 receptors plus the potential to be exploited as useful hits for the development of novel 2-AG mimetics.