2-[2-(4-Pyridin-2-yl-piperazin-1-yl)-ethyl]-1H-benzoimidazole | 767287-51-4

• 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-[2-(4-Pyridin-2-yl-piperazin-1-yl)-ethyl]-1H-benzoimidazole
• 英文别名: 2-[2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]-1H-benzimidazole
• CAS: 767287-51-4
• 化学式: C₁₈H₂₁N₅
• 分子量: 307.398
• InChiKey: SGQINIGEEAYUDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 2-(2-氯乙基)苯并咪唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以28%的产率得到2-[2-(4-Pyridin-2-yl-piperazin-1-yl)-ethyl]-1H-benzoimidazole
  参考文献：
  名称：

  Discovery of 2-(4-Pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a Dopaminergic Agent with a Novel Mode of Action for the Potential Treatment of Erectile Dysfunction

  摘要：

  A new class of agents with potential utility for the treatment of erectile dysfunction has been discovered, guided by the hypothesis that selective D-4 agonists are erectogenic but devoid of the side effects typically associated with dopaminergic agents. The lead agent 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (1, ABT-724) was discovered by optimization of a series of benzimidazole arylpiperazines. This highly selective D-4 agonist was found to be very potent and efficacious in vivo, eliciting penile erections in rats at a dose of 0.03 mumol/kg, with a positive response rate of 77% erectile incidence. Even at high doses, it was devoid of side effects in animal models of central nervous system behaviors, emesis, or nausea. The structure-activity relationship of the parent benzimidazole series leading to 1 is described, with the detailed in vitro and in vivo profiles described. Distinctive structural features were discovered that are associated with D-4 selective agonism in this series of analogues.

  DOI：

  10.1021/jm030505a