2-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-benzimidazole | 70006-22-3

• 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-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-benzimidazole
• 英文别名: 2-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-1H-benzimidazole
• CAS: 70006-22-3
• 化学式: C₁₉H₂₂N₄O
• 分子量: 322.41
• InChiKey: GRGYFXDAOZBGPF-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: acetone (67-64-1))
• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)
• 溶解度：
  47.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 在 甲烷磺酸 、 potassium carbonate 、 三乙胺 作用下， 以 水 、 丁酮 为溶剂， 反应 24.75h， 生成 2-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-benzimidazole
  参考文献：
  名称：

  Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor

  摘要：

  本研究共合成了 14 种新型芳基哌嗪，并通过[3H]spiperone 竞争试验测定了它们对 D2 多巴胺受体（DRD2）的亲和力，从而对其进行了药理评估。本文所述的所有化合物都由一个苯并咪唑分子通过不同长度的连接体与 N-(2-甲氧基苯基)哌嗪连接而成。研究人员对 DRD2 芳基哌嗪复合物进行了分子对接分析和分子动力学模拟，旨在探索受体与配体之间的相互作用以及受体结合位点的特性。本研究采用了最近公布的 DRD2 晶体结构。研究的主要发现是，高亲和力的芳基哌嗪必须同时与 DRD2 的正交结合位点和扩展结合口袋相互作用，因此应含有 5 或 6 个亚甲基长的连接基团。

  DOI：

  10.2298/jsc181029104p

文献信息

• Benzimidazoles that are useful in treating sexual dysfunction
  申请人：——

  公开号：US20030008878A1

  公开（公告）日：2003-01-09

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式（I）的化合物治疗性功能障碍，以及含有式（I）的化合物的组合物用于治疗性功能障碍。
• [EN] BENZIMIDAZOLES THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION<br/>[FR] BENZIMIDAZOLES UTILES DANS LE TRAITEMENT DE TROUBLES SEXUELS
  申请人：ABBOTT LAB

  公开号：WO2002088093A1

  公开（公告）日：2002-11-07

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)化合物治疗性功能障碍，以及含有式(I)化合物的组合物治疗性功能障碍。
• [EN] BENZIMIDAZOLE-DERIVATIVES FOR THE TREATMENT OF SEXUAL DYSFUNCTION<br/>[FR] DERIVES DE BENZIMIDAZOLE UTILISES POUR TRAITER UN DYSFONCTIONNEMENT SEXUEL
  申请人：ABBOTT LAB

  公开号：WO2003076431A1

  公开（公告）日：2003-09-18

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)的化合物的组合物治疗性功能障碍。
• Discovery of 2-(4-Pyridin-2-ylpiperazin-1-ylmethyl)-1<i>H</i>-benzimidazole (ABT-724), a Dopaminergic Agent with a Novel Mode of Action for the Potential Treatment of Erectile Dysfunction
  作者：Marlon Cowart、Steven P. Latshaw、Pramila Bhatia、Jerome F. Daanen、Jeffrey Rohde、Sherry L. Nelson、Meena Patel、Teodozyi Kolasa、Masaki Nakane、Marie E. Uchic、Loan N. Miller、Marc A. Terranova、Renjie Chang、Diana L. Donnelly-Roberts、Marian T. Namovic、Peter R. Hollingsworth、Brenda R. Martino、James J. Lynch、James P. Sullivan、Gin C. Hsieh、Robert B. Moreland、Jorge D. Brioni、Andrew O. Stewart

  DOI：10.1021/jm030505a

  日期：2004.7.1

  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.
• BENZIMIDAZOLES THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION
  申请人：ABBOTT LABORATORIES

  公开号：EP1373220A1

  公开（公告）日：2004-01-02