2-(3-Bromo-propyl)-tetrahydro-imidazo[1,5-a]pyridine-1,3-dione | 176218-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-(3-Bromo-propyl)-tetrahydro-imidazo[1,5-a]pyridine-1,3-dione
• 英文别名: 2-(3-bromopropyl)-6,7,8,8a-tetrahydro-5H-imidazo[1,5-a]pyridine-1,3-dione
• CAS: 176218-89-6
• 化学式: C₁₀H₁₅BrN₂O₂
• 分子量: 275.145
• InChiKey: DTNOHXRPXUAASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苯基哌嗪 、 2-(3-Bromo-propyl)-tetrahydro-imidazo[1,5-a]pyridine-1,3-dione 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以20%的产率得到2-[3-(4-phenylpiperazin-1-yl)propyl]-6,7,8,8a-tetrahydro-5H-imidazo[1,5-a]pyridine-1,3-dione
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a New Model of Arylpiperazines. 1. 2-[[4-(o-Methoxyphenyl)piperazin-1-yl]methyl]-1,3- dioxoperhydroimidazo[1,5-a]pyridine:  A Selective 5-HT_1A Receptor Agonist

  摘要：

  A series of new bicyclohydantoin-arylpiperazines was prepared and evaluated for affinity at 5-HT1A, alpha(1), and D-2 receptors. Most of the compounds showed very low affinity for D-2 receptors, and most of them demonstrated moderate to high affinity for 5-HT1A and alpha(1) receptor binding sites. SAR observations indicated that the length of the alkyl chain between the arylpiperazine and the hydantoin moiety is of great importance for 5-HT1A/alpha(1) affinity and selectivity, n = 1 being the optimal value. Compound 1h, 2-[[4-(o-methoxyphenyl)piperazin-1-yl]methyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine, bound at 5-HT1A sites with nanomolar affinity (K-i = 31.7 nM) and high selectivity over alpha(1), D-2, and 5-HT2A receptors (K-i > 1000, > 10 000, and > 1000 nM, respectively). Preliminary studies showed that this agent is probably functioning as a partial to full 5-HT1A agonist, and it displayed anxiolytic activity on the social interaction test in mice.

  DOI：

  10.1021/jm960416g
• 作为产物：
  描述：

  1,3-二溴丙烷 、 四氢咪唑并[1,5-a]吡啶-1,3(2H,5H)-二酮 在 sodium hydride 作用下， 生成 2-(3-Bromo-propyl)-tetrahydro-imidazo[1,5-a]pyridine-1,3-dione
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a New Model of Arylpiperazines. 1. 2-[[4-(o-Methoxyphenyl)piperazin-1-yl]methyl]-1,3- dioxoperhydroimidazo[1,5-a]pyridine:  A Selective 5-HT_1A Receptor Agonist

  摘要：

  A series of new bicyclohydantoin-arylpiperazines was prepared and evaluated for affinity at 5-HT1A, alpha(1), and D-2 receptors. Most of the compounds showed very low affinity for D-2 receptors, and most of them demonstrated moderate to high affinity for 5-HT1A and alpha(1) receptor binding sites. SAR observations indicated that the length of the alkyl chain between the arylpiperazine and the hydantoin moiety is of great importance for 5-HT1A/alpha(1) affinity and selectivity, n = 1 being the optimal value. Compound 1h, 2-[[4-(o-methoxyphenyl)piperazin-1-yl]methyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine, bound at 5-HT1A sites with nanomolar affinity (K-i = 31.7 nM) and high selectivity over alpha(1), D-2, and 5-HT2A receptors (K-i > 1000, > 10 000, and > 1000 nM, respectively). Preliminary studies showed that this agent is probably functioning as a partial to full 5-HT1A agonist, and it displayed anxiolytic activity on the social interaction test in mice.

  DOI：

  10.1021/jm960416g

文献信息

• 2-[4-(o-methoxyphenyl)piperazin-1-ylmethyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine as a new selective 5-HT1A receptor ligand
  作者：María L. López-Rodríguez、MaJosé Morcillo、MaLuisa Rosado、Bellinda Benhamu、Antonio M. Sanz

  DOI：10.1016/0960-894x(96)00081-9

  日期：1996.3

  A series of 2-[omega-(4-arylpiperazin-1-yl)alkyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine derivatives was prepared and evaluated for affinity at 5-HT1A and alpha(1) receptors. The most promising analogue Im bound at 5-HT1A sites with nanomolar affinity (K-i=31.7) and high selectivity over alpha(1), D-2 and 5-HT2A receptors (K-i>1000, K-i>10 000, K-i>1000 nM, respectively). Preliminary studies showed that this agent is a presynaptic 5-HT1A agonist, and it displayed activity in the face to face behavioural model.