trans-(±)-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-(±)-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide
• 英文别名: (+/-)-trans-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide；2-(2,6-dimethylphenoxy)-N-[(1R,2R)-2-hydroxycyclohexyl]acetamide
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: MITSQXUHQXSFGT-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-(±)-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide 在 氯化亚砜 作用下， 反应 3.0h， 生成 (1S,2R)-cis-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of trans- and cis-2-(2,6-dimethylphenoxy)-N-(2- or 4-hydroxycyclohexyl)acetamides and their amine analogs

  摘要：

  A group of trans-and cis-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamides (1-7) and -ethylamines (8-9) have been synthesized and investigated for their anticonvulsant activity. One of them, racemic trans-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl) acetamide proved to be the most effective in MES (mice, ip), exhibiting ED50 = 42.97 mg/kg b.w. and TD50 = 105.67 mg/kg b.w. It also proved protection in focal seizures (electric kindling, rats, ip) and it raises seizure threshold. The mechanism of action is inhibition of voltage-gated sodium currents and enhancement of GABA effect. Safety pharmacology assay on threshold tonic extension revealed no lowering of the seizure threshold. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.014
• 作为产物：
  描述：

  2,6-二甲基苯氧基乙酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 生成 trans-(±)-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of trans- and cis-2-(2,6-dimethylphenoxy)-N-(2- or 4-hydroxycyclohexyl)acetamides and their amine analogs

  摘要：

  A group of trans-and cis-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamides (1-7) and -ethylamines (8-9) have been synthesized and investigated for their anticonvulsant activity. One of them, racemic trans-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl) acetamide proved to be the most effective in MES (mice, ip), exhibiting ED50 = 42.97 mg/kg b.w. and TD50 = 105.67 mg/kg b.w. It also proved protection in focal seizures (electric kindling, rats, ip) and it raises seizure threshold. The mechanism of action is inhibition of voltage-gated sodium currents and enhancement of GABA effect. Safety pharmacology assay on threshold tonic extension revealed no lowering of the seizure threshold. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.014

文献信息

• Synthesis and anticonvulsant activity of trans- and cis-2-(2,6-dimethylphenoxy)-N-(2- or 4-hydroxycyclohexyl)acetamides and their amine analogs
  作者：Elżbieta Pękala、Anna M. Waszkielewicz、Edward Szneler、Maria Walczak、Henryk Marona

  DOI：10.1016/j.bmc.2011.09.014

  日期：2011.11

  A group of trans-and cis-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl)acetamides (1-7) and -ethylamines (8-9) have been synthesized and investigated for their anticonvulsant activity. One of them, racemic trans-2-(2,6-dimethylphenoxy)-N-(2-hydroxycyclohexyl) acetamide proved to be the most effective in MES (mice, ip), exhibiting ED50 = 42.97 mg/kg b.w. and TD50 = 105.67 mg/kg b.w. It also proved protection in focal seizures (electric kindling, rats, ip) and it raises seizure threshold. The mechanism of action is inhibition of voltage-gated sodium currents and enhancement of GABA effect. Safety pharmacology assay on threshold tonic extension revealed no lowering of the seizure threshold. (C) 2011 Elsevier Ltd. All rights reserved.