(S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-(4-(5-phenylpentyl)piperazin-1-yl)propan-1-one | 1535200-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-(4-(5-phenylpentyl)piperazin-1-yl)propan-1-one
• 英文别名: (2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-[4-(5-phenylpentyl)piperazin-1-yl]propan-1-one
• CAS: 1535200-76-0
• 化学式: C₂₆H₃₇N₃O₂
• 分子量: 423.599
• InChiKey: MKQISTQPDCMIKE-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯戊醇 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 6-氯-1-羟基苯并三氮唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-(4-(5-phenylpentyl)piperazin-1-yl)propan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of 4-substituted piperidines and piperazines as balanced affinity μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands

  摘要：

  In this letter, we describe a series of 4-substituted piperidine and piperazine compounds based on tetrahydroquinoline 1, a compound that shows balanced, low nanomolar binding affinity for the mu opioid receptor (MOR) and the delta opioid receptor (DOR). We have shown that by changing the length and flexibility profile of the side chain in this position, binding affinity is improved at both receptors by a significant degree. Furthermore, several of the compounds described herein display good efficacy at MOR, while simultaneously displaying DOR antagonism. The MOR agonist/DOR antagonist has shown promise in the reduction of negative side effects displayed by selective MOR agonists, namely the development of dependence and tolerance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.021

文献信息

• Synthesis and evaluation of 4-substituted piperidines and piperazines as balanced affinity μ opioid receptor (MOR) agonist/δ opioid receptor (DOR) antagonist ligands
  作者：Aaron M. Bender、Mary J. Clark、Michael P. Agius、John R. Traynor、Henry I. Mosberg

  DOI：10.1016/j.bmcl.2013.12.021

  日期：2014.1

  In this letter, we describe a series of 4-substituted piperidine and piperazine compounds based on tetrahydroquinoline 1, a compound that shows balanced, low nanomolar binding affinity for the mu opioid receptor (MOR) and the delta opioid receptor (DOR). We have shown that by changing the length and flexibility profile of the side chain in this position, binding affinity is improved at both receptors by a significant degree. Furthermore, several of the compounds described herein display good efficacy at MOR, while simultaneously displaying DOR antagonism. The MOR agonist/DOR antagonist has shown promise in the reduction of negative side effects displayed by selective MOR agonists, namely the development of dependence and tolerance. (C) 2013 Elsevier Ltd. All rights reserved.