1-(1-benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one | 149054-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(1-benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one
• 英文别名: 1-(1-Benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one；1-(1-benzylpiperidin-4-yl)-3,4-dihydroquinolin-2-one
• CAS: 149054-20-6
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: ZYIICKSWQGLDBO-UHFFFAOYSA-N

物化性质

• 沸点：
  521.1±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 1,2,3,4-tetrahydro-1-[1-(cyclooctyl)-4-piperidinyl]-quinolin-2-one
  参考文献：
  名称：

  Designing bifunctional NOP receptor–mu opioid receptor ligands from NOP receptor-selective scaffolds. Part I.

  摘要：

  The nociceptin receptor (NOP) and its endogenous agonist, nociceptin/orphanin FQ (N/OFQ), members of the opioid receptor and peptide families respectively, modulate the pharmacological effects of classical opioids, particularly opioid-induced reward and nociception. We hypothesized that compounds containing both NOP and opioid receptor activity in a single molecule may have useful pharmacological profiles as non-addicting analgesics or as drug abuse medications. We report here our forays into the structureactivity relationships for discovering 'bifunctional' NOP-mu opioid receptor (MOP) ligands, starting from our NOP-selective scaffolds. This initial SAR suggests pharmacophoric elements that may be modified to modulate/increase opioid affinity, while maintaining high affinity for the NOP receptor, to result in potent bifunctional small-molecule NOP/MOP ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.101
• 作为产物：
  描述：

  4-苯胺-1-苯甲基哌啶 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1-benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Designing bifunctional NOP receptor–mu opioid receptor ligands from NOP receptor-selective scaffolds. Part I.

  摘要：

  The nociceptin receptor (NOP) and its endogenous agonist, nociceptin/orphanin FQ (N/OFQ), members of the opioid receptor and peptide families respectively, modulate the pharmacological effects of classical opioids, particularly opioid-induced reward and nociception. We hypothesized that compounds containing both NOP and opioid receptor activity in a single molecule may have useful pharmacological profiles as non-addicting analgesics or as drug abuse medications. We report here our forays into the structureactivity relationships for discovering 'bifunctional' NOP-mu opioid receptor (MOP) ligands, starting from our NOP-selective scaffolds. This initial SAR suggests pharmacophoric elements that may be modified to modulate/increase opioid affinity, while maintaining high affinity for the NOP receptor, to result in potent bifunctional small-molecule NOP/MOP ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.101

文献信息

• Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives
  作者：G Rémond、B Portevin、J Bonnet、E Canet、D Regoli、G De Nanteuil

  DOI：10.1016/s0223-5234(97)82771-7

  日期：1997.11

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.
• Designing bifunctional NOP receptor–mu opioid receptor ligands from NOP receptor-selective scaffolds. Part I.
  作者：Nurulain T. Zaveri、Faming Jiang、Cris Olsen、Willma E. Polgar、Lawrence Toll

  DOI：10.1016/j.bmcl.2013.03.101

  日期：2013.6

  The nociceptin receptor (NOP) and its endogenous agonist, nociceptin/orphanin FQ (N/OFQ), members of the opioid receptor and peptide families respectively, modulate the pharmacological effects of classical opioids, particularly opioid-induced reward and nociception. We hypothesized that compounds containing both NOP and opioid receptor activity in a single molecule may have useful pharmacological profiles as non-addicting analgesics or as drug abuse medications. We report here our forays into the structureactivity relationships for discovering 'bifunctional' NOP-mu opioid receptor (MOP) ligands, starting from our NOP-selective scaffolds. This initial SAR suggests pharmacophoric elements that may be modified to modulate/increase opioid affinity, while maintaining high affinity for the NOP receptor, to result in potent bifunctional small-molecule NOP/MOP ligands. (C) 2013 Elsevier Ltd. All rights reserved.