N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepan-4-yl)propionamide | 1536470-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepan-4-yl)propionamide
• 英文别名: N-phenyl-N-[1-(2-thiophen-2-ylethyl)azepan-4-yl]propanamide
• CAS: 1536470-25-3
• 化学式: C₂₁H₂₈N₂OS
• 分子量: 356.532
• InChiKey: JMBXBTYIZOYHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepan-4-yl)propionamide 、 柠檬酸 以 异丙醇 为溶剂， 以86%的产率得到N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepan-4-yl)propionamide citrate
  参考文献：
  名称：

  Synthesis and antinociceptive properties of N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide in the mouse tail-flick and hot-plate tests

  摘要：

  The goals of this study, were to synthesize N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide (1c) and determine its antinociceptive properties. The effect of clonidine on 1c antinociception and the involvement of opioid, alpha(2)-adrenergic, and I-2 imidazoline receptors in 1c antinociception were studied. Also examined was the effect of an endothelin ETA receptor antagonist on 1c antinociception. Synthesis of 1c was accomplished in two steps using modifications of previously reported methods. Antinociceptive (tail-flick and hot-plate) latencies were measured in male Swiss Webster mice treated with 1c; antagonists + 1c; clonidine + 1c; or antagonists + clonidine + 1c. Mice were pretreated with naloxone (opioid antagonist), yohimbine (alpha(2)-adrenoceptor antagonist), idazoxan (alpha(2)-adrenoceptor/I-2-imidazoline antagonist), BU224 (I-2-imidazoline antagonist) or BQ123 (endothelin ETA receptor antagonist) to study the involvement of these receptors. Compound 1c produced a dose-dependent increase in antinociceptive latencies; ED50 values were 0.15 mg/kg and 0.16 mg/kg, respectively, in the tail flick and hot plate tests. Naloxone, but not yohimbine, idazoxan or BU224, blocked 1c antinociception. Neither clonidine nor BQ123 potentiated 1c antinociception. Results demonstrate that 1c is 15-times more potent than morphine. The antinociceptive effect of 1c is mediated through opioid receptors. The alpha(2)-adrenergic, I-2-imidazoline and endothelin ETA receptors are not involved in 1c antinociception. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.069
• 作为产物：
  描述：

  2-(2-噻吩基)乙基甲烷磺酸酯 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 乙腈 、 苯 为溶剂， 反应 23.0h， 生成 N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepan-4-yl)propionamide
  参考文献：
  名称：

  Synthesis and antinociceptive properties of N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide in the mouse tail-flick and hot-plate tests

  摘要：

  The goals of this study, were to synthesize N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide (1c) and determine its antinociceptive properties. The effect of clonidine on 1c antinociception and the involvement of opioid, alpha(2)-adrenergic, and I-2 imidazoline receptors in 1c antinociception were studied. Also examined was the effect of an endothelin ETA receptor antagonist on 1c antinociception. Synthesis of 1c was accomplished in two steps using modifications of previously reported methods. Antinociceptive (tail-flick and hot-plate) latencies were measured in male Swiss Webster mice treated with 1c; antagonists + 1c; clonidine + 1c; or antagonists + clonidine + 1c. Mice were pretreated with naloxone (opioid antagonist), yohimbine (alpha(2)-adrenoceptor antagonist), idazoxan (alpha(2)-adrenoceptor/I-2-imidazoline antagonist), BU224 (I-2-imidazoline antagonist) or BQ123 (endothelin ETA receptor antagonist) to study the involvement of these receptors. Compound 1c produced a dose-dependent increase in antinociceptive latencies; ED50 values were 0.15 mg/kg and 0.16 mg/kg, respectively, in the tail flick and hot plate tests. Naloxone, but not yohimbine, idazoxan or BU224, blocked 1c antinociception. Neither clonidine nor BQ123 potentiated 1c antinociception. Results demonstrate that 1c is 15-times more potent than morphine. The antinociceptive effect of 1c is mediated through opioid receptors. The alpha(2)-adrenergic, I-2-imidazoline and endothelin ETA receptors are not involved in 1c antinociception. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.069

文献信息

• Synthesis and antinociceptive properties of N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide in the mouse tail-flick and hot-plate tests
  作者：Shridhar V. Andurkar、Madhu Shaw J. Reniguntala、Anil Gulati、Jack DeRuiter

  DOI：10.1016/j.bmcl.2013.11.069

  日期：2014.1

  The goals of this study, were to synthesize N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide (1c) and determine its antinociceptive properties. The effect of clonidine on 1c antinociception and the involvement of opioid, alpha(2)-adrenergic, and I-2 imidazoline receptors in 1c antinociception were studied. Also examined was the effect of an endothelin ETA receptor antagonist on 1c antinociception. Synthesis of 1c was accomplished in two steps using modifications of previously reported methods. Antinociceptive (tail-flick and hot-plate) latencies were measured in male Swiss Webster mice treated with 1c; antagonists + 1c; clonidine + 1c; or antagonists + clonidine + 1c. Mice were pretreated with naloxone (opioid antagonist), yohimbine (alpha(2)-adrenoceptor antagonist), idazoxan (alpha(2)-adrenoceptor/I-2-imidazoline antagonist), BU224 (I-2-imidazoline antagonist) or BQ123 (endothelin ETA receptor antagonist) to study the involvement of these receptors. Compound 1c produced a dose-dependent increase in antinociceptive latencies; ED50 values were 0.15 mg/kg and 0.16 mg/kg, respectively, in the tail flick and hot plate tests. Naloxone, but not yohimbine, idazoxan or BU224, blocked 1c antinociception. Neither clonidine nor BQ123 potentiated 1c antinociception. Results demonstrate that 1c is 15-times more potent than morphine. The antinociceptive effect of 1c is mediated through opioid receptors. The alpha(2)-adrenergic, I-2-imidazoline and endothelin ETA receptors are not involved in 1c antinociception. (C) 2013 Elsevier Ltd. All rights reserved.