3-(2-chloro-5-methylphenoxy)propyl bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-chloro-5-methylphenoxy)propyl bromide
• 英文别名: 2-(3-Bromopropoxy)-1-chloro-4-methylbenzene
• 化学式: C₁₀H₁₂BrClO
• 分子量: 263.562
• InChiKey: AIRDZFBSJJQNDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 3-(2-chloro-5-methylphenoxy)propyl bromide 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-[3-(2-Chloro-5-methylphenoxy)propyl]-4-(2-methoxyphenyl)piperazine
  参考文献：
  名称：

  Synthesis and Evaluation of Antidepressant-like Activity of Some 4-Substituted 1-(2-methoxyphenyl)Piperazine Derivatives

  摘要：

  A series of new derivatives of N‐(2‐methoxyphenyl)piperazine have been synthesized for their affinity toward serotonergic receptors and for their potential antidepressant‐like activity. They have been evaluated toward receptors 5‐HT1A, 5‐HT6, and 5‐HT7, as well as in vivo in the tail suspension, locomotor activity, and motor co‐ordination tests. All the tested compounds proved very good affinities toward 5‐HT1A and 5‐HT7 receptors. The most promising compound was 1‐[(2‐chloro‐6‐methylphenoxy)ethoxyethyl]‐4‐(2‐methoxyphenyl)piperazine hydrochloride, exhibiting affinity toward receptors Ki <1 nm (5‐HT1A) and Ki = 34 nm (5‐HT7). Antidepressant‐like activity (tail suspension test) was observed at 2.5 mg/kg b.w. (mice, i.p.), and the effect was stronger than that observed for imipramine (5 mg/kg b.w.). Sedative activity was observed at ED50 (locomotor test, mice, i.p.) = 17.5 mg/kg b.w. and neurotoxicity was observed at TD50 (rotarod, mice, i.p.) = 53.2 mg/kg b.w.

  DOI：

  10.1111/cbdd.12394
• 作为产物：
  描述：

  2-氯-5-甲酚 、 3-氯-1-丙醇 在 potassium carbonate 、 三溴化磷 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-(2-chloro-5-methylphenoxy)propyl bromide
  参考文献：
  名称：

  Synthesis and Evaluation of Antidepressant-like Activity of Some 4-Substituted 1-(2-methoxyphenyl)Piperazine Derivatives

  摘要：

  A series of new derivatives of N‐(2‐methoxyphenyl)piperazine have been synthesized for their affinity toward serotonergic receptors and for their potential antidepressant‐like activity. They have been evaluated toward receptors 5‐HT1A, 5‐HT6, and 5‐HT7, as well as in vivo in the tail suspension, locomotor activity, and motor co‐ordination tests. All the tested compounds proved very good affinities toward 5‐HT1A and 5‐HT7 receptors. The most promising compound was 1‐[(2‐chloro‐6‐methylphenoxy)ethoxyethyl]‐4‐(2‐methoxyphenyl)piperazine hydrochloride, exhibiting affinity toward receptors Ki <1 nm (5‐HT1A) and Ki = 34 nm (5‐HT7). Antidepressant‐like activity (tail suspension test) was observed at 2.5 mg/kg b.w. (mice, i.p.), and the effect was stronger than that observed for imipramine (5 mg/kg b.w.). Sedative activity was observed at ED50 (locomotor test, mice, i.p.) = 17.5 mg/kg b.w. and neurotoxicity was observed at TD50 (rotarod, mice, i.p.) = 53.2 mg/kg b.w.

  DOI：

  10.1111/cbdd.12394

文献信息

• Synthesis and Evaluation of Antidepressant-like Activity of Some 4-Substituted 1-(2-methoxyphenyl)Piperazine Derivatives
  作者：Anna M. Waszkielewicz、Karolina Pytka、Anna Rapacz、Elżbieta Wełna、Monika Jarzyna、Grzegorz Satała、Andrzej Bojarski、Jacek Sapa、Paweł Żmudzki、Barbara Filipek、Henryk Marona

  DOI：10.1111/cbdd.12394

  日期：2015.3

  A series of new derivatives of N‐(2‐methoxyphenyl)piperazine have been synthesized for their affinity toward serotonergic receptors and for their potential antidepressant‐like activity. They have been evaluated toward receptors 5‐HT1A, 5‐HT6, and 5‐HT7, as well as in vivo in the tail suspension, locomotor activity, and motor co‐ordination tests. All the tested compounds proved very good affinities toward 5‐HT1A and 5‐HT7 receptors. The most promising compound was 1‐[(2‐chloro‐6‐methylphenoxy)ethoxyethyl]‐4‐(2‐methoxyphenyl)piperazine hydrochloride, exhibiting affinity toward receptors Ki <1 nm (5‐HT1A) and Ki = 34 nm (5‐HT7). Antidepressant‐like activity (tail suspension test) was observed at 2.5 mg/kg b.w. (mice, i.p.), and the effect was stronger than that observed for imipramine (5 mg/kg b.w.). Sedative activity was observed at ED50 (locomotor test, mice, i.p.) = 17.5 mg/kg b.w. and neurotoxicity was observed at TD50 (rotarod, mice, i.p.) = 53.2 mg/kg b.w.