trans-(4-methyl-1-(nitromethyl)cyclohexyl)acetic acid ethyl ester | 205827-01-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-(4-methyl-1-(nitromethyl)cyclohexyl)acetic acid ethyl ester
• CAS: 205827-01-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: ZGTLQAYSQFPEHW-UMSPYCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-(4-methyl-1-(nitromethyl)cyclohexyl)acetic acid ethyl ester 在 Ra-Ni 盐酸 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 35.0 ℃ 、275.79 kPa 条件下， 反应 22.0h， 生成
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n
• 作为产物：
  描述：

  4-甲基环己酮 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.75h， 生成 trans-(4-methyl-1-(nitromethyl)cyclohexyl)acetic acid ethyl ester
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n

文献信息

• Investigation into the preferred conformation of gabapentin for interaction with its binding site on the α2δ subunit of a calcium channel
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Jacqueline A. O'Neill、Giles S. Ratcliffe

  DOI：10.1016/s0960-894x(97)10002-6

  日期：1997.10

  A series of conformationally restricted Gabapentin analogues has been synthesised and used to propose the preferred conformation of Gabapentin for it to bind to the alpha(2) delta subunit of a calcium channel. (C) 1997 Elsevier Science Ltd.