| 1350724-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• CAS: 1350724-60-5
• 化学式: C₂₉H₄₈O₆
• 分子量: 492.697
• InChiKey: DBHNVZSQUCJHAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以78%的产率得到2,3-dihydroxypropyl 11-(4-hexyl-3-hydroxyphenoxy)undecanoate
  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
• 作为产物：
  描述：

  丙酮缩甘油 在 4-二甲氨基吡啶 、 potassium fluoride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 48.5h， 生成
  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