1,1-bis<2-<1-(4-methoxybenzyl)imidazolyl>>ethylene | 161227-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-bis<2-<1-(4-methoxybenzyl)imidazolyl>>ethylene
• 英文别名: 1-[(4-Methoxyphenyl)methyl]-2-[1-[1-[(4-methoxyphenyl)methyl]imidazol-2-yl]ethenyl]imidazole
• CAS: 161227-65-2
• 化学式: C₂₄H₂₄N₄O₂
• 分子量: 400.48
• InChiKey: BPSHJMGOUDMSFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-bis<2-<1-(4-methoxybenzyl)imidazolyl>>ethylene 在 盐酸 、 Dowex 1X 2-200 ion exchange resin 、 三氟乙酸 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 122.0h， 生成 6,11-ethano-12,12-di(2'-imidazolyl)-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：

  Bis-[1-(4-methoxy-benzyl)-1H-imidazol-2-yl]-methanone 、 亚甲基三苯基膦烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以35%的产率得到1,1-bis<2-<1-(4-methoxybenzyl)imidazolyl>>ethylene
  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

• An Unusual dependency of counterion during wittig methylenation of bis-heteroaryl ketones
  作者：Chakrapani Subramanyam

  DOI：10.1016/0040-4039(95)02016-i

  日期：1995.12

  Attempted Wittig methylenation of some bis-heteroaromatic ketones (8, 11 and 13) using MeP(+)Ph(3)Br and n-BuLi gave none of the desired olefin. However, when KtBuO was used as the base for generation of the ylide, efficient olefination of these ketones was observed. A possible mechanistic pathway for this interesting but unprecedented observation is proposed.
• 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.