1,1-di(2-thiazolyl)-2-trimethylsilylethanol | 161227-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1-di(2-thiazolyl)-2-trimethylsilylethanol
• 英文别名: 1,1-Bis(1,3-thiazol-2-yl)-2-trimethylsilylethanol
• CAS: 161227-55-0
• 化学式: C₁₁H₁₆N₂OS₂Si
• 分子量: 284.478
• InChiKey: ILNUDPBEBFIUQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzoquinolizinium perchlorate 、 1,1-di(2-thiazolyl)-2-trimethylsilylethanol 在 对甲苯磺酸 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以10%的产率得到6,11-ethano-12,12-di(2'-thiazolyl)-6,11-dihydrobenzoquinolizinium perchlorate
  参考文献：
  名称：

  Discovery of 6,11-Ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium Cations, a Novel Class of N-Methyl-D-aspartate Antagonists

  摘要：

  6,11-Ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium cations 8, a novel class of N-methyl-D-aspartate (NMDA) antagonists acting at the phencyclidine site, have been identified. Structure-activity relationship studies around the lead compound 8a led to the identification of 12g (WIN 67870-2), one of the most potent compounds in this series. Compound 12g has a K-i = 1.8 +/- 0.2 nM vs [H-3]TCP binding, has 700-fold selectivity for binding to the open state of the NMDA receptor-ionophore, and was devoid of MK-801- and PCP-like behavioral effects in rats. Compound 12g was neuroprotective in cultured mouse cortical neurons and exhibited antiischemic activity in a rat middle cerebral artery occlusion/reperfusion model of focal ischemia.

  DOI：

  10.1021/jm00001a006
• 作为产物：
  描述：

  (三甲基硅基)甲基氯化镁 、 二噻唑-2-基甲酮 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以39%的产率得到1,1-di(2-thiazolyl)-2-trimethylsilylethanol
  参考文献：
  名称：

  Discovery of 6,11-Ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium Cations, a Novel Class of N-Methyl-D-aspartate Antagonists

  摘要：

  6,11-Ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium cations 8, a novel class of N-methyl-D-aspartate (NMDA) antagonists acting at the phencyclidine site, have been identified. Structure-activity relationship studies around the lead compound 8a led to the identification of 12g (WIN 67870-2), one of the most potent compounds in this series. Compound 12g has a K-i = 1.8 +/- 0.2 nM vs [H-3]TCP binding, has 700-fold selectivity for binding to the open state of the NMDA receptor-ionophore, and was devoid of MK-801- and PCP-like behavioral effects in rats. Compound 12g was neuroprotective in cultured mouse cortical neurons and exhibited antiischemic activity in a rat middle cerebral artery occlusion/reperfusion model of focal ischemia.

  DOI：

  10.1021/jm00001a006