3-(4-Fluoro-benzyl)-4-{4-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperazin-1-yl}-butyric acid methyl ester | 133496-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-Fluoro-benzyl)-4-{4-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperazin-1-yl}-butyric acid methyl ester
• CAS: 133496-63-6
• 化学式: C₂₆H₃₂F₂N₂O₃
• 分子量: 458.548
• InChiKey: UFWSBFXKCVZRQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-Fluoro-benzyl)-4-{4-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperazin-1-yl}-butyric acid methyl ester 在 PPA 作用下， 反应 5.0h， 以43%的产率得到6-fluoro-3-[[4-[4-(4-fluorophenyl)-4-oxobutyl]piperazin-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
• 作为产物：
  描述：

  2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 盐酸 、 sodium carbonate 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 34.0h， 生成 3-(4-Fluoro-benzyl)-4-{4-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperazin-1-yl}-butyric acid methyl ester
  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