2-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one

• 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: 2-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one
• 英文别名: 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one
• 化学式: C₂₀H₂₄ClN₅O
• 分子量: 385.896
• InChiKey: KNYIQWUXTSJAQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 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 、 xylene 为溶剂， 反应 13.0h， 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

文献信息

• ALKYL DERIVATIVES OF TRAZODONE WITH CNS ACTIVITY
  申请人：ANGELINI RICERCHE S.p.A. SOCIETA' CONSORTILE

  公开号：EP0623131B1

  公开（公告）日：1996-04-03
• 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.