3-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2H-naphthalen-1-one | 133496-59-0

• 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: 3-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2H-naphthalen-1-one
• CAS: 133496-59-0
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: QXPWDQWINFEIAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苯基-4-羟基哌啶 在 PPA 、 sodium carbonate 、 potassium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 25.0h， 生成 3-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Synthesis and antidopaminergic activity of some 3-(aminomethyl)tetralones as analogs of butyrophenone

  摘要：

  Starting from beta-benzoylpropionic acid was synthesized 3-(aminomethyl)tetralones in which the amino substituent was 4-(N-piperazinyl)-p-fluorobutyrophenone (14), 4-benzoylpiperidine (15), 4-hydroxy-4-phenylpiperidine (16) or 4-(o-methoxyphenyl)piperazine (17). The possible dopamine antagonist activity of these compounds was investigated in both ''in vitro'' and ''in vivo'' experiments. These compounds potently inhibited [H-3]spiperone binding to D2 striatal receptors and moderately inhibited [H-3]SCH-23390 binding to D1 striatal receptors (K(i)s in the nanomolar and micromolar ranges, respectively). Apomorphine-induced stereotypies and amphetamine group toxicity were antagonized, to different extents, by the compounds under study, with a potency similar to that of haloperidol. Interestingly, no catalepsy was observed after administration of the new compounds (2-8 mg/kg). The most active compounds ''in vivo'' 14 and 15 possessed two butyrophenone pharmacophores. However, the tetralone moiety appeared not critical for their antidopaminergic activity, since all target compounds were less active than haloperidol. These studies provide a pharmacological basis for future research on these new compounds devoid of cataleptogenic activity.

  DOI：

  10.1021/jm00111a046

文献信息

• Synthesis and antidopaminergic activity of some 3-(aminomethyl)tetralones as analogs of butyrophenone
  作者：Lourdes Cortizo、Lourdes Santana、Enrique Ravina、Francisco Orallo、Jose A. Fontenla、Elena Castro、Jose M. Calleja、Maria L. De Ceballos

  DOI：10.1021/jm00111a046

  日期：1991.7

  Starting from beta-benzoylpropionic acid was synthesized 3-(aminomethyl)tetralones in which the amino substituent was 4-(N-piperazinyl)-p-fluorobutyrophenone (14), 4-benzoylpiperidine (15), 4-hydroxy-4-phenylpiperidine (16) or 4-(o-methoxyphenyl)piperazine (17). The possible dopamine antagonist activity of these compounds was investigated in both ''in vitro'' and ''in vivo'' experiments. These compounds potently inhibited [H-3]spiperone binding to D2 striatal receptors and moderately inhibited [H-3]SCH-23390 binding to D1 striatal receptors (K(i)s in the nanomolar and micromolar ranges, respectively). Apomorphine-induced stereotypies and amphetamine group toxicity were antagonized, to different extents, by the compounds under study, with a potency similar to that of haloperidol. Interestingly, no catalepsy was observed after administration of the new compounds (2-8 mg/kg). The most active compounds ''in vivo'' 14 and 15 possessed two butyrophenone pharmacophores. However, the tetralone moiety appeared not critical for their antidopaminergic activity, since all target compounds were less active than haloperidol. These studies provide a pharmacological basis for future research on these new compounds devoid of cataleptogenic activity.