1-iodo-3-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]azulene | 1414890-25-7

• 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-iodo-3-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]azulene
• 英文别名: 1-[(3-Iodoazulen-1-yl)methyl]-4-(2-methoxyphenyl)piperazine；1-[(3-iodoazulen-1-yl)methyl]-4-(2-methoxyphenyl)piperazine
• CAS: 1414890-25-7
• 化学式: C₂₂H₂₃IN₂O
• 分子量: 458.342
• InChiKey: LAOQDPODHTVQOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-iodo-3-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]azulene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 1-[(3-Ethynylazulen-1-yl)methyl]-4-(2-methoxyphenyl)piperazine
  参考文献：
  名称：

  Novel azulene derivatives for the treatment of erectile dysfunction

  摘要：

  Based on the dopamine D-4 receptor partial agonist FAUC 3019, a series of azulenylmethylpiperazines was synthesized and affinities for the monoaminergic GPCRs including dopamine, serotonin, histamine and alpha-adrenergic receptor subtypes were determined. Ligand efficacies of the most promising test compounds revealed the N,N-dimethylaminomethyl substituted azulene 11 to be the most potent D-4 partial agonist (EC50 = 0.41 nM). This candidate was investigated for its ability to promote penile erection. Applying an in vivo animal model, test compound 11 turned out to stimulate penile erection in male rats with superior potency in low concentrations when compared to apomorphine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.064
• 作为产物：
  描述：

  FAUC 3019 在 N-碘代丁二酰亚胺 作用下， 以 苯 为溶剂， 反应 3.0h， 以68%的产率得到1-iodo-3-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]azulene
  参考文献：
  名称：

  Novel azulene derivatives for the treatment of erectile dysfunction

  摘要：

  Based on the dopamine D-4 receptor partial agonist FAUC 3019, a series of azulenylmethylpiperazines was synthesized and affinities for the monoaminergic GPCRs including dopamine, serotonin, histamine and alpha-adrenergic receptor subtypes were determined. Ligand efficacies of the most promising test compounds revealed the N,N-dimethylaminomethyl substituted azulene 11 to be the most potent D-4 partial agonist (EC50 = 0.41 nM). This candidate was investigated for its ability to promote penile erection. Applying an in vivo animal model, test compound 11 turned out to stimulate penile erection in male rats with superior potency in low concentrations when compared to apomorphine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.064

文献信息

• Novel azulene derivatives for the treatment of erectile dysfunction
  作者：Stefan Löber、Harald Hübner、Armin Buschauer、Fabrizio Sanna、Antonio Argiolas、Maria Rosaria Melis、Peter Gmeiner

  DOI：10.1016/j.bmcl.2012.09.064

  日期：2012.12

  Based on the dopamine D-4 receptor partial agonist FAUC 3019, a series of azulenylmethylpiperazines was synthesized and affinities for the monoaminergic GPCRs including dopamine, serotonin, histamine and alpha-adrenergic receptor subtypes were determined. Ligand efficacies of the most promising test compounds revealed the N,N-dimethylaminomethyl substituted azulene 11 to be the most potent D-4 partial agonist (EC50 = 0.41 nM). This candidate was investigated for its ability to promote penile erection. Applying an in vivo animal model, test compound 11 turned out to stimulate penile erection in male rats with superior potency in low concentrations when compared to apomorphine. (C) 2012 Elsevier Ltd. All rights reserved.