3,4-dihydro-1-oxonaphthalene-2(1H)-spiro-4'-<1'-(naphthylmethyl)piperidine>

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-1-oxonaphthalene-2(1H)-spiro-4'-<1'-(naphthylmethyl)piperidine>
• 英文别名: 3,4-dihydro-1-oxonaphthalene-2(1H)-spiro-4'-[1'-(naphthylmethyl)piperidine]；1''-(2-Naphthylmethyl)spiro[1,2,3,4-tetrahydronaphthalene-2,4''-(hexahydropyridine)]-1-one;malate；1'-(naphthalen-2-ylmethyl)spiro[3,4-dihydronaphthalene-2,4'-piperidine]-1-one
• 化学式: C₂₅H₂₅NO
• 分子量: 355.48
• InChiKey: ZYQPFSVYWPFCAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1-oxonaphthalene-2(1H)-spiro-4'-<1'-(naphthylmethyl)piperidine> 生成 1''-[4-(4-fluorophenyl)-4-oxobutyl]-3,4-dihydro-1H-spiro[naphthalene-2,4''-piperidine]-1-one chloride
  参考文献：
  名称：

  Gilligan Paul J., Kergaye Ahmed A., Lewis Bryan M., McElroy John F., J. Med. Chem, 37 (1994) N 3, S 364-370

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-4-哌啶甲酸乙酯 在 sodium hydroxide 、 甲烷磺酸 、 phosphorus pentoxide 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 80.5h， 生成 3,4-dihydro-1-oxonaphthalene-2(1H)-spiro-4'-<1'-(naphthylmethyl)piperidine>
  参考文献：
  名称：

  Piperidinyltetralin .sigma. Ligands

  摘要：

  sigma receptor ligands have been proposed to be potential antipsychotic drugs based on their activity profile in animal behavioral models and their indirect modulation of dopaminergic function. Compound 15 (DuP 734) is a combined antagonist of sigma-1 and serotonin 5HT(2) receptors, which has been entered into phase I clinical trials as a potential antipsychotic drug. Tetralins 1 and 2 were prepared to determine whether restriction of the conformation of 15 and its analogs may lead to differences in binding selectivity or in vivo profile. The syntheses and the structure-activity relationships of these compounds are reported herein. A reduced derivative, 14, had high affinity for sigma-1 and serotonin 5HT(2) receptors as well as excellent oral activity in some animal antipsychotic models. Furthermore, compound 14 failed to cause catalepsy in the rat up to 90 mg/kg (po).

  DOI：

  10.1021/jm00029a008