Bis-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-methanone | 161227-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bis-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-methanone
• 英文别名: Methanone, bis[1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-5-yl]-；bis[2-(2-trimethylsilylethoxymethyl)pyrazol-3-yl]methanone
• CAS: 161227-60-7
• 化学式: C₁₉H₃₄N₄O₃Si₂
• 分子量: 422.675
• InChiKey: FBYSZCWDFVQJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  71.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Bis-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-methanone 在 盐酸 、 Dowex 1X 2-200 ion exchange resin 、 三氟乙酸 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 6,11-ethano-12,12-di(3'-pyrazolyl)-6,11-dihydrobenzo[b]quinolizinium chloride
  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：

  N-甲氧基-N-甲基氨基甲酸乙酯 、 三甲基-[2-(吡唑-1-基甲氧基)乙基]硅烷 在 正丁基锂 作用下， 生成 Bis-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-methanone
  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

文献信息

• Discovery of 6,11-Ethano-12,12-diaryl-6,11-dihydrobenzo[b]quinolizinium Cations, a Novel Class of N-Methyl-D-aspartate Antagonists
  作者：Chakrapani Subramanyam、John P. Mallamo、John A. Dority、William G. Earley、Virendra Kumar、Lisa D. Aimone、Brian Ault、Matthew S. Miller、Daniel A. Luttinger、Diane L. DeHaven-Hudkins

  DOI：10.1021/jm00001a006

  日期：1995.1

  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.