3-[4-(2-Methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propan-1-one | 302561-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[4-(2-Methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propan-1-one
• CAS: 302561-60-0
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: XBVDXFWLSQGZHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(2-Methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以45%的产率得到3-[4-(2-Methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propan-1-ol
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives as potential antidepressants with a dual mode of action: serotonin reuptake inhibition and 5-HT1A receptor antagonism

  摘要：

  It has been suggested that the combination of a selective serotonin reuptake inhibitor (SSRI) and a 5-HT1A receptor antagonist may facilitate the onset of the SSRIs antidepressant action. Accordingly, we describe the synthesis of a series of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives with structural modifications performed in Ar-1, Ar-2 and Z (Z is different functional groups) to obtain the sought dual activity. Compounds were evaluated for in vitro affinity at 5-HT1A receptors and 5-HT transporter. The antidepressant-like activity of derivatives with the higher affinity was assessed initially using the forced swimming test (FST). Compound 1 -(2,4-dimethylphenyl)-3-[(2-methoxyphenyl)piperazin-1-il]-1-propanone (III.1.a) showed the best antidepressant-like activity which was further confirmed in the learned helplessness test. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00050-1
• 作为产物：
  描述：

  聚合甲醛 、 1-(2-methoxyphenyl)piperazine hydrochloride 、 对甲基苯乙酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以44%的产率得到3-[4-(2-Methoxyphenyl)piperazin-1-yl]-1-(4-methylphenyl)propan-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives as potential antidepressants with a dual mode of action: serotonin reuptake inhibition and 5-HT1A receptor antagonism

  摘要：

  It has been suggested that the combination of a selective serotonin reuptake inhibitor (SSRI) and a 5-HT1A receptor antagonist may facilitate the onset of the SSRIs antidepressant action. Accordingly, we describe the synthesis of a series of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives with structural modifications performed in Ar-1, Ar-2 and Z (Z is different functional groups) to obtain the sought dual activity. Compounds were evaluated for in vitro affinity at 5-HT1A receptors and 5-HT transporter. The antidepressant-like activity of derivatives with the higher affinity was assessed initially using the forced swimming test (FST). Compound 1 -(2,4-dimethylphenyl)-3-[(2-methoxyphenyl)piperazin-1-il]-1-propanone (III.1.a) showed the best antidepressant-like activity which was further confirmed in the learned helplessness test. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00050-1

文献信息

• Design, synthesis and biological evaluation of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives as potential antidepressants with a dual mode of action: serotonin reuptake inhibition and 5-HT1A receptor antagonism
  作者：A.M Oficialdegui、J Martinez、S Pérez、B Heras、M Irurzun、J.A Palop、R Tordera、B Lasheras、J del Rı́o、A Monge

  DOI：10.1016/s0014-827x(00)00050-1

  日期：2000.5

  It has been suggested that the combination of a selective serotonin reuptake inhibitor (SSRI) and a 5-HT1A receptor antagonist may facilitate the onset of the SSRIs antidepressant action. Accordingly, we describe the synthesis of a series of new 3-[(4-aryl)piperazin-1-yl]-1-arylpropane derivatives with structural modifications performed in Ar-1, Ar-2 and Z (Z is different functional groups) to obtain the sought dual activity. Compounds were evaluated for in vitro affinity at 5-HT1A receptors and 5-HT transporter. The antidepressant-like activity of derivatives with the higher affinity was assessed initially using the forced swimming test (FST). Compound 1 -(2,4-dimethylphenyl)-3-[(2-methoxyphenyl)piperazin-1-il]-1-propanone (III.1.a) showed the best antidepressant-like activity which was further confirmed in the learned helplessness test. (C) 2000 Elsevier Science S.A. All rights reserved.