Bis-[1-(4-methoxy-benzyl)-1H-imidazol-2-yl]-methanone | 161227-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Bis-[1-(4-methoxy-benzyl)-1H-imidazol-2-yl]-methanone
• 英文别名: Bis[1-[(4-methoxyphenyl)methyl]imidazol-2-yl]methanone
• CAS: 161227-64-1
• 化学式: C₂₃H₂₂N₄O₃
• 分子量: 402.453
• InChiKey: KZXMKGLIZRFMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  71.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Bis-[1-(4-methoxy-benzyl)-1H-imidazol-2-yl]-methanone 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 反应 98.0h， 生成 16,16-bis[1-[(4-methoxyphenyl)methyl]imidazol-2-yl]-2-azoniatetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene;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：

  N-甲氧基-N-甲基氨基甲酸乙酯 、 1-(4-甲氧基-苄基)-1H-吡唑 在 正丁基锂 作用下， 生成 Bis-[1-(4-methoxy-benzyl)-1H-imidazol-2-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

• Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts and compositionsand methods of use thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0656359A1

  公开（公告）日：1995-06-07

  Substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts of Formula, pharmaceutical compositions containing them, and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  式中的取代的 6,11-乙hano-6,11-二氢苯并[b]喹嗪盐、 含有它们的药物组合物，以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• 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.
• US5554620A
  申请人：——

  公开号：US5554620A

  公开（公告）日：1996-09-10
• US5631264A
  申请人：——

  公开号：US5631264A

  公开（公告）日：1997-05-20
• 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.