4-(3-chlorophenyl)-1-(3-chloro-1-methylpropyl)piperazine | 151447-89-1

• 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: 4-(3-chlorophenyl)-1-(3-chloro-1-methylpropyl)piperazine
• 英文别名: 1-(3-chlorophenyl)-4-(3-chloro-1-methylpropyl)piperazine；1-(4-Chlorobutan-2-yl)-4-(3-chlorophenyl)piperazine
• CAS: 151447-89-1
• 化学式: C₁₄H₂₀Cl₂N₂
• 分子量: 287.232
• InChiKey: HAYVIRCKQRTVNC-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：
  0.57
• 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：

  4-(3-chlorophenyl)-1-(3-chloro-1-methylpropyl)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]-butyl}-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-(3-氯苯基)哌嗪 在 氯化亚砜 、 sodium ethanolate 、 红铝 作用下， 以 乙醚 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 5.0h， 生成 4-(3-chlorophenyl)-1-(3-chloro-1-methylpropyl)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：EP0623131A1

  公开（公告）日：1994-11-09
• 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
• [EN] ALKYL DERIVATIVES OF TRAZODONE WITH CNS ACTIVITY
  申请人：ISTITUTO RICERCA FRANCESCO ANGELINI S.P.A.

  公开号：WO1993014091A1

  公开（公告）日：1993-07-22

  (EN) Compounds of formula (I), wherein only one of R, R', R'' and R' '' is 1-3 C alkyl, and the others are H, as antidepressants.(FR) Composés répondant à la formule (I), dans laquelle un seul parmi R, R', R' et R'' représente alkyle C1-3 et les autres représentent H, et servant d'antidépresseurs.
• Effect of Modifications of the Alkylpiperazine Moiety of Trazodone on 5HT_2A and α₁ Receptor Binding Affinity
  作者：Marilena Giannangeli、Nicola Cazzolla、Maria Rita Luparini、Maurizio Magnani、Massimo Mabilia、Giuseppe Picconi、Mauro Tomaselli、Leandro Baiocchi

  DOI：10.1021/jm970700n

  日期：1999.2.1

  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.