1(2H)-Naphthalenone,3,4-dihydro-2-[[4-(4-methylphenyl)-1-piperazinyl]methyl]- | 885101-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1(2H)-Naphthalenone,3,4-dihydro-2-[[4-(4-methylphenyl)-1-piperazinyl]methyl]-
• CAS: 885101-13-3
• 化学式: C₂₂H₂₆N₂O
• 分子量: 334.461
• InChiKey: HGZPIDKCCSNHAG-UHFFFAOYSA-N

物化性质

• 熔点：
  171-175 °C
• 沸点：
  509.9±50.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1(2H)-Naphthalenone,3,4-dihydro-2-[[4-(4-methylphenyl)-1-piperazinyl]methyl]- 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 生成 cis-1-(4-methylphenyl)-4-[1-(4-acetylphenoxy)-1,2,3,4-tetrahydronaphthalen-2-ylmethyl]piperazine
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032
• 作为产物：
  描述：

  1-(4-methylphenyl)piperazine hydrochloride 、 聚合甲醛 、 3,4-二氢-1(2H)-萘酮 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 5.25h， 以77%的产率得到1(2H)-Naphthalenone,3,4-dihydro-2-[[4-(4-methylphenyl)-1-piperazinyl]methyl]-
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032