(R)-4-phenylamino-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)-piperidine-4-carbonitrile | 228246-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-4-phenylamino-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)-piperidine-4-carbonitrile
• 英文别名: (R)-4-Phenylamino-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-carbonitrile；4-anilino-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]piperidine-4-carbonitrile
• CAS: 228246-71-7
• 化学式: C₂₂H₂₅N₃
• 分子量: 331.461
• InChiKey: QMZXLRFPPZNYPK-OAQYLSRUSA-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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-phenylamino-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)-piperidine-4-carbonitrile 在 ammonium hydroxide 作用下， 以 乙酸酐 、 叔丁醇 为溶剂， 反应 92.0h， 生成 (R)-1-phenyl-8-(1,2,3,4-tetrahydro-naphthalen-1-yl)-1,3,8-triaza-spiro[4.5]decan-4-one
  参考文献：
  名称：

  High-Affinity, Non-Peptide Agonists for the ORL1 (Orphanin FQ/Nociceptin) Receptor

  摘要：

  The discovery of 8-(5,8-dichloro-1,2,3,4-tetrahydro-naphthalen-2-yl)-1-phenyl-1,3,8-triazaspiro [4.5]decan-4-one, 1a, as a high-affinity ligand for the human ORL1 (orphanin FQ/nociceptin) receptor led to the synthesis of a series of optimized Ligands. These compounds exhibit high affinity for the human ORL1 receptor, exhibit moderate to good selectivity versus opioid receptors, and behave as full agonists in biochemical assays. In this paper we present the synthesis, structure-activity relationship (SAR), and biochemical characterization of substituted 1-phenyl-1,3,8-triazaspiro [4.5]decan-4-ones culminating in the discovery of 8-(5-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-1-phenyl-1,3,8-triazaspiro [4.5] decan-4-one, 1p, and 8-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1q, two high-affinity, potent ORL1 receptor agonists with good to moderate selectivity versus the other opioid receptors.

  DOI：

  10.1021/jm991129q
• 作为产物：
  描述：

  1-乙基-1-甲基-4-氧代哌啶-1-碘化物 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 (R)-4-phenylamino-1-(1,2,3,4-tetrahydro-naphthalen-1-yl)-piperidine-4-carbonitrile
  参考文献：
  名称：

  High-Affinity, Non-Peptide Agonists for the ORL1 (Orphanin FQ/Nociceptin) Receptor

  摘要：

  The discovery of 8-(5,8-dichloro-1,2,3,4-tetrahydro-naphthalen-2-yl)-1-phenyl-1,3,8-triazaspiro [4.5]decan-4-one, 1a, as a high-affinity ligand for the human ORL1 (orphanin FQ/nociceptin) receptor led to the synthesis of a series of optimized Ligands. These compounds exhibit high affinity for the human ORL1 receptor, exhibit moderate to good selectivity versus opioid receptors, and behave as full agonists in biochemical assays. In this paper we present the synthesis, structure-activity relationship (SAR), and biochemical characterization of substituted 1-phenyl-1,3,8-triazaspiro [4.5]decan-4-ones culminating in the discovery of 8-(5-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-1-phenyl-1,3,8-triazaspiro [4.5] decan-4-one, 1p, and 8-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1q, two high-affinity, potent ORL1 receptor agonists with good to moderate selectivity versus the other opioid receptors.

  DOI：

  10.1021/jm991129q

文献信息

• 8-substituted-1,3,8-triazaspiro[4.5]decan-4-on derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0856514B1

  公开（公告）日：2001-06-13
• US6071925A
  申请人：——

  公开号：US6071925A

  公开（公告）日：2000-06-06
• High-Affinity, Non-Peptide Agonists for the ORL1 (Orphanin FQ/Nociceptin) Receptor
  作者：Stephan Röver、Geo Adam、Andrea M. Cesura、Guido Galley、François Jenck、Frederick J. Monsma,、Jürgen Wichmann、Frank M. Dautzenberg

  DOI：10.1021/jm991129q

  日期：2000.4.6

  The discovery of 8-(5,8-dichloro-1,2,3,4-tetrahydro-naphthalen-2-yl)-1-phenyl-1,3,8-triazaspiro [4.5]decan-4-one, 1a, as a high-affinity ligand for the human ORL1 (orphanin FQ/nociceptin) receptor led to the synthesis of a series of optimized Ligands. These compounds exhibit high affinity for the human ORL1 receptor, exhibit moderate to good selectivity versus opioid receptors, and behave as full agonists in biochemical assays. In this paper we present the synthesis, structure-activity relationship (SAR), and biochemical characterization of substituted 1-phenyl-1,3,8-triazaspiro [4.5]decan-4-ones culminating in the discovery of 8-(5-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-1-phenyl-1,3,8-triazaspiro [4.5] decan-4-one, 1p, and 8-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1q, two high-affinity, potent ORL1 receptor agonists with good to moderate selectivity versus the other opioid receptors.