2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-([(11)C]-methyloxy)ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]amide | 1244958-61-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-([(11)C]-methyloxy)ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]amide
• 英文别名: [(11)C]-A-836339
• CAS: 1244958-61-9
• 化学式: C₁₆H₂₆N₂O₂S
• 分子量: 309.45
• InChiKey: JKGIMVBQKSRTGX-DOBXWLEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.59
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-hydroxyethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]amide 、 [11C]methyl triflate 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 生成 2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-([(11)C]-methyloxy)ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]amide
  参考文献：
  名称：

  Synthesis and biodistribution of [11C]A-836339, a new potential radioligand for PET imaging of cannabinoid type 2 receptors (CB2)

  摘要：

  Recently, A-836339 [2,2,3,3-tetramethylcyclopropanecarboxylic acid [3-(2-methoxyethyl)-4,5-dimethyl3H- thiazol-(2Z)-ylidene] amide] (1) was reported to be a selective CB2 agonist with high binding affinity. Here we describe the radiosynthesis of [C-11] A-836339 ([C-11] 1) via its desmethyl precursor as a candidate radioligand for imaging CB2 receptors with positron-emission tomography (PET). Whole body and the regional brain distribution of [C-11] 1 in control CD1 mice demonstrated that this radioligand exhibits specific uptake in the CB2-rich spleen and little specific in vivo binding in the control mouse brain. However, [C-11] 1 shows specific cerebral uptake in the lipopolysaccharide (LPS)-induced mouse model of neuroinflammation and in the brain areas with A beta amyloid plaque deposition in a mouse model of Alzheimer's disease (APPswe/PS1dE9 mice). These data establish a proof of principle that CB2 receptors binding in the neuroinflammation and related disorders can be measured in vivo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.058