1'-cyclohexylmethylspiro[indane-1,4'-piperidine] | 137730-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1'-cyclohexylmethylspiro[indane-1,4'-piperidine]
• 英文别名: 1'-(Cyclohexylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine]
• CAS: 137730-54-2
• 化学式: C₂₀H₂₉N
• 分子量: 283.457
• InChiKey: XWGDOCSDEQCYHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-二氢螺(茚-1,4-哌啶) 、 溴甲基环己烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1'-cyclohexylmethylspiro[indane-1,4'-piperidine]
  参考文献：
  名称：

  Spiropiperidines as high-affinity, selective .sigma. ligands.

  摘要：

  A variety of achiral conformationally restricted spirocyclic piperidines have been prepared in an attempt to investigate the functional role of the central sigma-recognition site. All the compounds possessed a lipophilic N-substituent incorporating either a tetralin, indan, or benzocycloheptane skeleton. Their in vitro affinity at the sigma-site was assessed in radioligand displacement experiments with guinea pig cerebellum homogenates using the sigma-specific radioligand [H-3]-N,N'-di-o-tolyguanidine ([H-3]-DTG, [H-3]-6). A study of the structure-activity relationships identified the N-butyl and N-dimethylallyl substituents as the optimum groups for high affinity and selectivity at the sigma-site (e.g., 3,4-dihydro-1'-(3-methylbut-2-enyl)spiro[1H-indene-1,4'-piperidine] (48), pIC50 = 8.9 vs [3H]-6 and greater than 10000-fold selective over the dopamine D2 receptor). Such compounds are amongst the highest affinity sigma-ligands reported to date, with excellent selectivity over the dopamine D2 receptor, and may serve as at useful tool for exploring the physiological role of the sigma-site.

  DOI：

  10.1021/jm00089a013

文献信息

• Spirocyclic antipsychotic agents
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0445974A2

  公开（公告）日：1991-09-11

  A class of spirocyclic piperidine derivatives are selective ligands at sigma recognition sites and are therefore useful in the treatment and/or prevention of psychiatric disorders.

  一类螺环哌啶衍生物是σ识别位点的选择性配体，因此可用于治疗和/或预防精神疾病。
• SPIRO-ISOQUINOLINE-1,4'-PIPERIDINE COMPOUNDS HAVING MULTIMODAL ACTIVITY AGAINST PAIN
  申请人：ESTEVE PHARMACEUTICALS, S.A.

  公开号：EP3221314B1

  公开（公告）日：2019-07-03
• US5219860A
  申请人：——

  公开号：US5219860A

  公开（公告）日：1993-06-15
• US5324733A
  申请人：——

  公开号：US5324733A

  公开（公告）日：1994-06-28
• Spiropiperidines as high-affinity, selective .sigma. ligands.
  作者：Mark S. Chambers、Raymond Baker、David C. Billington、Anthony K. Knight、D. N. Middlemiss、Eric H. F. Wong

  DOI：10.1021/jm00089a013

  日期：1992.5

  A variety of achiral conformationally restricted spirocyclic piperidines have been prepared in an attempt to investigate the functional role of the central sigma-recognition site. All the compounds possessed a lipophilic N-substituent incorporating either a tetralin, indan, or benzocycloheptane skeleton. Their in vitro affinity at the sigma-site was assessed in radioligand displacement experiments with guinea pig cerebellum homogenates using the sigma-specific radioligand [H-3]-N,N'-di-o-tolyguanidine ([H-3]-DTG, [H-3]-6). A study of the structure-activity relationships identified the N-butyl and N-dimethylallyl substituents as the optimum groups for high affinity and selectivity at the sigma-site (e.g., 3,4-dihydro-1'-(3-methylbut-2-enyl)spiro[1H-indene-1,4'-piperidine] (48), pIC50 = 8.9 vs [3H]-6 and greater than 10000-fold selective over the dopamine D2 receptor). Such compounds are amongst the highest affinity sigma-ligands reported to date, with excellent selectivity over the dopamine D2 receptor, and may serve as at useful tool for exploring the physiological role of the sigma-site.