1-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine | 151447-87-9

• 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-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine
• 英文别名: 1-(3-chlorophenyl)-4-(3-chloro-2-methylpropyl)-piperazine；1-(3-Chloro-2-methylpropyl)-4-(3-chlorophenyl)piperazine
• CAS: 151447-87-9
• 化学式: C₁₄H₂₀Cl₂N₂
• mdl: MFCD19101373
• 分子量: 287.232
• InChiKey: UGCJWRJSEQWGTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine 、 1,2,4-triazolo<4,3-a>pyridin-3(2H)-one sodium salt 以 xylene 为溶剂， 反应 8.0h， 生成 2-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propyl}-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one
  参考文献：
  名称：

  Effect of Modifications of the Alkylpiperazine Moiety of Trazodone on 5HT_2A and α₁ Receptor Binding Affinity

  摘要：

  A series of triazolopyridine derivatives (compounds 2a-I) were synthesized in order to-explore the effect of modifications of the alkylpiperazine moiety of trazodone (fragment A) on binding affinity for 5HT(2A) and alpha(1) receptors. All of the synthesized compounds show a decrease of affinity for both 5HT(2A) and alpha(1) receptors, as compared to trazodone, with the exception of compounds 2b,c which bear a methyl group in an alpha position to the aliphatic nitrogen atom N-1. These compounds showed a decrease of affinity only for the alpha(1) receptor. The stereochemical influence of the piperazine moiety of compound 2c was also evaluated. Enantiomer (S)-2c showed the most significant differences between 5HT(2A) and alpha(1) receptor affinity (IC50 values) and among the corresponding functional properties (pA(2) values). Since (S)-2c cannot generate the metabolite 4-(3-chlorophenyl)piperazine this product was selected for further pharmacological studies.

  DOI：

  10.1021/jm970700n
• 作为产物：
  描述：

  1-溴-3-氯-2-甲基丙烷 、 1-(3-氯苯基)哌嗪 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 以57%的产率得到1-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine
  参考文献：
  名称：

  Effect of Modifications of the Alkylpiperazine Moiety of Trazodone on 5HT_2A and α₁ Receptor Binding Affinity

  摘要：

  A series of triazolopyridine derivatives (compounds 2a-I) were synthesized in order to-explore the effect of modifications of the alkylpiperazine moiety of trazodone (fragment A) on binding affinity for 5HT(2A) and alpha(1) receptors. All of the synthesized compounds show a decrease of affinity for both 5HT(2A) and alpha(1) receptors, as compared to trazodone, with the exception of compounds 2b,c which bear a methyl group in an alpha position to the aliphatic nitrogen atom N-1. These compounds showed a decrease of affinity only for the alpha(1) receptor. The stereochemical influence of the piperazine moiety of compound 2c was also evaluated. Enantiomer (S)-2c showed the most significant differences between 5HT(2A) and alpha(1) receptor affinity (IC50 values) and among the corresponding functional properties (pA(2) values). Since (S)-2c cannot generate the metabolite 4-(3-chlorophenyl)piperazine this product was selected for further pharmacological studies.

  DOI：

  10.1021/jm970700n

文献信息

• Alkyl derivatives of trazodone with CNS activity
  申请人：Istituto Ricerca Francesco Angelini S.p.A.

  公开号：US05543563A1

  公开（公告）日：1996-08-06

  Alkyl derivatives of trazodone endowed with pharmacological activity, pharmaceutical compositions containing them, process for preparing them and intermediate compounds useful in their preparation.

  特拉唑酮的烷基衍生物具有药理活性，包含它们的药物组合物，制备它们的方法以及在其制备中有用的中间化合物。
• ALKYL DERIVATIVES OF TRAZODONE WITH CNS ACTIVITY
  申请人：ISTITUTO RICERCA FRANCESCO ANGELINI S.p.A.

  公开号：EP0623131A1

  公开（公告）日：1994-11-09
• US5543563A
  申请人：——

  公开号：US5543563A

  公开（公告）日：1996-08-06
• US5726178A
  申请人：——

  公开号：US5726178A

  公开（公告）日：1998-03-10
• US5739334A
  申请人：——

  公开号：US5739334A

  公开（公告）日：1998-04-14