1-(1-Diethoxymethyl-4-ethynyl-1H-pyrrol-2-ylmethyl)-4-phenyl-piperazine | 490576-22-2

• 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-(1-Diethoxymethyl-4-ethynyl-1H-pyrrol-2-ylmethyl)-4-phenyl-piperazine
• 英文别名: 1-[[1-(Diethoxymethyl)-4-ethynylpyrrol-2-yl]methyl]-4-phenylpiperazine；1-[[1-(diethoxymethyl)-4-ethynylpyrrol-2-yl]methyl]-4-phenylpiperazine
• CAS: 490576-22-2
• 化学式: C₂₂H₂₉N₃O₂
• 分子量: 367.491
• InChiKey: OWKFEQBOLKAILD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-Diethoxymethyl-4-ethynyl-1H-pyrrol-2-ylmethyl)-4-phenyl-piperazine 在 三氟乙酸 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.4h， 以56%的产率得到1-(4-Ethynyl-1H-pyrrol-2-ylmethyl)-4-phenyl-piperazine
  参考文献：
  名称：

  2,4-Disubstituted pyrroles: synthesis, traceless linking and pharmacological investigations leading to the dopamine D4 receptor partial agonist FAUC 356

  摘要：

  Solution-phase synthesis and a solid-phase supported approach to piperazinylmethyl substituted pyrroles are described. Receptor binding studies and the measurement of D4 ligand efficacy led to the ethynylpyrrole 1d (FAUC 356) exerting selective D4 binding and substantial ligand efficacy (66%, EC50 = 1.9 nM). This activity profile might be of interest for the treatment of ADHD. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00316-5
• 作为产物：
  描述：

  1-diethoxymethyl-4-trimethylsilylethinyl-1H-pyrrole-2-carbaldehyde 在 四丁基氟化铵 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 1-(1-Diethoxymethyl-4-ethynyl-1H-pyrrol-2-ylmethyl)-4-phenyl-piperazine
  参考文献：
  名称：

  2,4-Disubstituted pyrroles: synthesis, traceless linking and pharmacological investigations leading to the dopamine D4 receptor partial agonist FAUC 356

  摘要：

  Solution-phase synthesis and a solid-phase supported approach to piperazinylmethyl substituted pyrroles are described. Receptor binding studies and the measurement of D4 ligand efficacy led to the ethynylpyrrole 1d (FAUC 356) exerting selective D4 binding and substantial ligand efficacy (66%, EC50 = 1.9 nM). This activity profile might be of interest for the treatment of ADHD. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00316-5

文献信息

• 2,4-Disubstituted pyrroles: synthesis, traceless linking and pharmacological investigations leading to the dopamine D4 receptor partial agonist FAUC 356
  作者：Markus Bergauer、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(02)00316-5

  日期：2002.8

  Solution-phase synthesis and a solid-phase supported approach to piperazinylmethyl substituted pyrroles are described. Receptor binding studies and the measurement of D4 ligand efficacy led to the ethynylpyrrole 1d (FAUC 356) exerting selective D4 binding and substantial ligand efficacy (66%, EC50 = 1.9 nM). This activity profile might be of interest for the treatment of ADHD. (C) 2002 Elsevier Science Ltd. All rights reserved.