(E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone o-2-(2-(tertbutyldimethylsilyloxy)ethoxy)ethyl oxime | 1239586-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone o-2-(2-(tertbutyldimethylsilyloxy)ethoxy)ethyl oxime
• CAS: 1239586-82-3
• 化学式: C₂₁H₃₂N₂O₃SSi
• 分子量: 420.648
• InChiKey: HDXVRAFTXVBICP-FCDQGJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.94
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone o-2-(2-(tertbutyldimethylsilyloxy)ethoxy)ethyl oxime 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone o-2-(2-hydroxyethoxy)-ethyl oxime
  参考文献：
  名称：

  Syntheses and pharmacological characterization of novel thiazole derivatives as potential mGluR5 PET ligands

  摘要：

  Four novel thiazole containing ABP688 derivatives were synthesized and evaluated for their binding affinity towards the metabotropic glutamate receptor subtype 5 (mGluR5). (E)-3-((2-(Fluoromethyl)thiazol-4-yl)ethynyl)cyclohex-2-enone O-methyl oxime (FTECMO), the ligand with the highest binding affinity (K-i = 5.5 +/- 1.1 nM), was labeled with fluorine-18. [F-18]-FTECMO displayed optimal lipophilicity (log D-pH7.4 = 1.6 +/- 0.2) and high stability in rat and human plasma as well as sufficient stability in rat liver microsomes. In vitro autoradiography with [F-18]-FTECMO revealed a heterogeneous and displaceable binding in mGluR5-rich brain regions. PET imaging with [F-18]-FTECMO in Wistar rats, however, showed low brain uptake. Uptake of radioactivity into the skull was observed suggesting in vivo defluorination. Thus, although [F-18]-FTECMO is an excellent ligand for the detection of mGluR5 in vitro, its in vivo characteristics are not optimal for the imaging of mGluR5 in rats in vivo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.070
• 作为产物：
  描述：

  (2-(2-bromoethoxy)ethoxy)(tert-butyl)dimethylsilane 、 (E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone oxime 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 以80%的产率得到(E)-3-(thiazol-4-ylethynyl)cyclohex-2-enone o-2-(2-(tertbutyldimethylsilyloxy)ethoxy)ethyl oxime
  参考文献：
  名称：

  Syntheses and pharmacological characterization of novel thiazole derivatives as potential mGluR5 PET ligands

  摘要：

  Four novel thiazole containing ABP688 derivatives were synthesized and evaluated for their binding affinity towards the metabotropic glutamate receptor subtype 5 (mGluR5). (E)-3-((2-(Fluoromethyl)thiazol-4-yl)ethynyl)cyclohex-2-enone O-methyl oxime (FTECMO), the ligand with the highest binding affinity (K-i = 5.5 +/- 1.1 nM), was labeled with fluorine-18. [F-18]-FTECMO displayed optimal lipophilicity (log D-pH7.4 = 1.6 +/- 0.2) and high stability in rat and human plasma as well as sufficient stability in rat liver microsomes. In vitro autoradiography with [F-18]-FTECMO revealed a heterogeneous and displaceable binding in mGluR5-rich brain regions. PET imaging with [F-18]-FTECMO in Wistar rats, however, showed low brain uptake. Uptake of radioactivity into the skull was observed suggesting in vivo defluorination. Thus, although [F-18]-FTECMO is an excellent ligand for the detection of mGluR5 in vitro, its in vivo characteristics are not optimal for the imaging of mGluR5 in rats in vivo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.070