5-(15,15-dimethyl-henicosa-all-cis-4,7,10,13-tetraenyloxy)-2-phenyl-[1,3]dioxane | 886220-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 5-(15,15-dimethyl-henicosa-all-cis-4,7,10,13-tetraenyloxy)-2-phenyl-[1,3]dioxane
• CAS: 886220-07-1
• 化学式: C₃₃H₅₀O₃
• 分子量: 494.758
• InChiKey: LWIBZPMETMOHLI-LTOJCMOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.29
• 重原子数：
  36.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(15,15-dimethyl-henicosa-all-cis-4,7,10,13-tetraenyloxy)-2-phenyl-[1,3]dioxane 在 盐酸 、 甲醇 作用下， 反应 3.0h， 以37%的产率得到2-(15,15-dimethyl-henicosa-all-cis-4,7,10,13-tetraenyloxy)-propane-1,3-diol
  参考文献：
  名称：

  Synthesis and CB1 receptor activities of dimethylheptyl derivatives of 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE)

  摘要：

  Results from a factor analysis and activity studies of commercially available endocannabinoid-type compounds set the starting point for the current study where dimethylheptyl (DMH) analogues of two endocannabinoids, 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE), were synthesized and their ability to activate the CB1 receptors was determined by the [S-35]GTP gamma S binding assay using rat cerebellar membranes. The main goal of the study was to examine how the DMH end tail affects the activity properties of 2-AG (1) and its stable ether (2) and Urea analogues (5). The importance of the chain length was also explored by synthesizing 2-AG and 2-AGE derivatives (3 and 4) possessing the chain length C-21 instead of C-22. Replacement of the pentyl end chain with the DMH resulted in distinct potency decrease as compared to the reference compounds. The modification did not have Such a strong impact on the efficacy values. In fact, the efficacy of the derivatives of 2-AGE (2 and 4) was comparable or even improved. Introducing a more stable and hydrophilic urea bond led to a dramatic decrease in biological activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.007
• 作为产物：
  描述：

  (4Z,7Z,10Z,13Z)-15,15-Dimethyl-henicosa-4,7,10,13-tetraen-1-ol 在 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 5-(15,15-dimethyl-henicosa-all-cis-4,7,10,13-tetraenyloxy)-2-phenyl-[1,3]dioxane
  参考文献：
  名称：

  Synthesis and CB1 receptor activities of dimethylheptyl derivatives of 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE)

  摘要：

  Results from a factor analysis and activity studies of commercially available endocannabinoid-type compounds set the starting point for the current study where dimethylheptyl (DMH) analogues of two endocannabinoids, 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE), were synthesized and their ability to activate the CB1 receptors was determined by the [S-35]GTP gamma S binding assay using rat cerebellar membranes. The main goal of the study was to examine how the DMH end tail affects the activity properties of 2-AG (1) and its stable ether (2) and Urea analogues (5). The importance of the chain length was also explored by synthesizing 2-AG and 2-AGE derivatives (3 and 4) possessing the chain length C-21 instead of C-22. Replacement of the pentyl end chain with the DMH resulted in distinct potency decrease as compared to the reference compounds. The modification did not have Such a strong impact on the efficacy values. In fact, the efficacy of the derivatives of 2-AGE (2 and 4) was comparable or even improved. Introducing a more stable and hydrophilic urea bond led to a dramatic decrease in biological activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.007