1-(3-chlorophenyl)-3-methylpiperazin-2-one | 151447-78-8

• 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)-3-methylpiperazin-2-one
• CAS: 151447-78-8
• 化学式: C₁₁H₁₃ClN₂O
• 分子量: 224.69
• InChiKey: FUASZNDGQOZKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-chlorophenyl)-3-methylpiperazin-2-one 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 生成 (S)-1-(3-chlorophenyl)-3-methylpiperazine
  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：

  N-(3-chlorophenyl)-1,2-ethanediamine 在 盐酸 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 1-(3-chlorophenyl)-3-methylpiperazin-2-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

• [EN] PHARMACOLOGICALLY ACTIVE ENANTIOMERS<br/>[FR] ENANTIOMERES PHARMACOLOGIQUEMENT ACTIFS
  申请人：ANGELINI RICERCHE S.P.A. SOCIETA' CONSORTILE

  公开号：WO1995001354A1

  公开（公告）日：1995-01-12

  (EN) (S) or (R) enantiomer of a compound of formula (IA), where Alk is an alkyl having from 1 to 3 carbon atoms, and an acid addition salt thereof with a physiologically acceptable acid.(FR) L'invention se rapporte à des énantiomères (S) ou (R) de formule (IA) dans laquelle Alk est un alkyle ayant de 1 à 3 atomes de carbone, ainsi qu'à un sel d'addition d'acide de ces composés, que l'on obtient par l'addition d'un acide acceptable physiologiquement.

  （EN）或（R）对于化学式（IA）的化合物的对映体，其中Alk是具有1至3个碳原子的烷基，以及其与一种生理上可接受的酸形成的酸加成盐。（FR）公式（IA）化合物的（S）或（R）对映体，其中Alk是具有1至3个碳原子的烷基，以及其与一种生理上可接受的酸形成的酸加成盐。
• 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
• PHARMACOLOGICALLY ACTIVE ENANTIOMERS
  申请人：ANGELINI RICERCHE S.p.A. SOCIETA' CONSORTILE

  公开号：EP0707587B1

  公开（公告）日：1997-10-01
• 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