(4-(nitromethyl)tetrahydrothiopyran-4-yl)acetic acid ethyl ester | 194862-85-6

• 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: (4-(nitromethyl)tetrahydrothiopyran-4-yl)acetic acid ethyl ester
• 英文别名: Ethyl 2-[4-(nitromethyl)thian-4-yl]acetate
• CAS: 194862-85-6
• 化学式: C₁₀H₁₇NO₄S
• 分子量: 247.315
• InChiKey: GREPXGUMGFTIQY-UHFFFAOYSA-N

物化性质

• 沸点：
  364.5±7.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-(nitromethyl)tetrahydrothiopyran-4-yl)acetic acid ethyl ester 在 盐酸 、 tin(ll) chloride 作用下， 反应 2.0h， 以26%的产率得到2-[4-(Aminomethyl)thian-4-yl]acetic acid;hydrochloride
  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：

  四氢噻喃-4-酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 1,1,2,3-四甲基胍 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 (4-(nitromethyl)tetrahydrothiopyran-4-yl)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

• [EN] INFLUENZA VIRUS INHIBITOR AND USE THEREOF<br/>[FR] INHIBITEUR DU VIRUS DE LA GRIPPE ET SON UTILISATION<br/>[ZH] 一种流感病毒抑制剂及其用途
  申请人：YANGTZE RIVER PHARM GROUP CO

  公开号：WO2022171198A1

  公开（公告）日：2022-08-18

  提供式（I）、式（II）、式（III）和式（IV）所示的作为流感病毒复制抑制剂的化合物及其在制备用于预防或治疗流感的药物中的用途。
• Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、Visaka U. K. Dissanayake、Giles S. Ratcliffe、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Ryszard J. Oles、John C. O'Toole、Gemma M. Perkins、Lakhbir Singh、Nirmala Suman-Chauhan、Jacqueline A. O'Neill

  DOI：10.1021/jm970649n

  日期：1998.5.1

  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.