(1S,3aR)-1-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile | 309254-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,3aR)-1-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile
• 英文别名: 1-[(1S,3aR)-2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl]-4-anilinopiperidine-4-carbonitrile
• CAS: 309254-84-0
• 化学式: C₂₅H₂₉N₃
• 分子量: 371.525
• InChiKey: KUKOJDQQZFMKPO-OFNKIYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (1S,3aR)-1-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile 在 原甲酸三乙酯 作用下， 以 乙酸酐 为溶剂， 生成 8-[(1S,3aR)-2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
  参考文献：
  名称：

  Synthesis of (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties

  摘要：

  The development of 8-(2,3,3a,4,5,6-hexahydro-1H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-ones 3 starting from (RS)-s-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1 is reported. The synthesis and the binding affinities at human OFQ and opioid (mu, kappa, delta) receptors of the stereoisomers 3a-f are described. In vitro the most selective compound, (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1 H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 3c, was found to act as a full agonist at the OFQ receptor in the GTP gamma(35)S binding test. It turned out to be selective versus a variety of other neurotransmitter systems. When tested in vivo following intraperitoneal injection, compound 3c was found to decrease neophobia in a novel environment and to exhibit dose-dependent anxiolytic-like effects in the elevated plus-maze procedure, thus confirming the effects observed following intracerebroventricular infusion of the OFQ peptide in rat. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00171-9
• 作为产物：
  描述：

  3-(3,4-dihydronaphthalen-1-yl)propanoic acid 在 ruthenium bis(acetate) 、 镍 、 (R)-(+)-(6,6′-二甲氧联苯-2,2′-二基)双(二苯基膦) 盐酸羟胺 、 氨 、 氢气 、 sodium acetate 、 potassium carbonate 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 溶剂黄146 、 三氟乙酸 为溶剂， 20.0~70.0 ℃ 、10.0 MPa 条件下， 生成 (1S,3aR)-1-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile
  参考文献：
  名称：

  Synthesis of (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties

  摘要：

  The development of 8-(2,3,3a,4,5,6-hexahydro-1H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-ones 3 starting from (RS)-s-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1 is reported. The synthesis and the binding affinities at human OFQ and opioid (mu, kappa, delta) receptors of the stereoisomers 3a-f are described. In vitro the most selective compound, (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1 H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 3c, was found to act as a full agonist at the OFQ receptor in the GTP gamma(35)S binding test. It turned out to be selective versus a variety of other neurotransmitter systems. When tested in vivo following intraperitoneal injection, compound 3c was found to decrease neophobia in a novel environment and to exhibit dose-dependent anxiolytic-like effects in the elevated plus-maze procedure, thus confirming the effects observed following intracerebroventricular infusion of the OFQ peptide in rat. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00171-9

文献信息

• Synthesis of (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, a potent and selective orphanin FQ (OFQ) receptor agonist with anxiolytic-like properties
  作者：J Wichmann

  DOI：10.1016/s0223-5234(00)00171-9

  日期：2000.9

  The development of 8-(2,3,3a,4,5,6-hexahydro-1H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-ones 3 starting from (RS)-s-acenaphten-1-yl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 1 is reported. The synthesis and the binding affinities at human OFQ and opioid (mu, kappa, delta) receptors of the stereoisomers 3a-f are described. In vitro the most selective compound, (1S,3aS)-8-(2,3,3a,4,5,6-hexahydro-1 H-phenalenl-yl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 3c, was found to act as a full agonist at the OFQ receptor in the GTP gamma(35)S binding test. It turned out to be selective versus a variety of other neurotransmitter systems. When tested in vivo following intraperitoneal injection, compound 3c was found to decrease neophobia in a novel environment and to exhibit dose-dependent anxiolytic-like effects in the elevated plus-maze procedure, thus confirming the effects observed following intracerebroventricular infusion of the OFQ peptide in rat. (C) 2000 Editions scientifiques et medicales Elsevier SAS.