7-[4-(4-Chloro-benzyl)-piperazin-1-ylmethyl]-4-hydroxy-chromen-2-one; hydrochloride | 75590-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-[4-(4-Chloro-benzyl)-piperazin-1-ylmethyl]-4-hydroxy-chromen-2-one; hydrochloride
• CAS: 75590-56-6
• 化学式: C₂₁H₂₁ClN₂O₃*2ClH
• 分子量: 457.784
• InChiKey: CSLDXIBDSOTZKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.92
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-[4-(4-Chloro-benzyl)-piperazin-1-ylmethyl]-4-hydroxy-chromen-2-one; hydrochloride 在 硝酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以70%的产率得到1-(4-chlorobenzyl)-4-[(4-hydroxy-3-nitrocoumarin-7-yl)methyl]piperazine
  参考文献：
  名称：

  N-Benzylpiperazino derivatives of 3-nitro-4-hydroxycoumarin with H1 antihistamine and mast cell stabilizing properties

  摘要：

  In a small range finding study a number of N-benzylpiperazino derivates of 3-nitro-4-hydroxycoumarin have been shown to combine potent H1-antihistamine activity with that of mast cell stabilization as demonstrated by their activity as antagonists of histamine on guinea pig ileum and by their inhibition of the release of histamine in rat passive peritoneal anaphylaxis (PPA). The most potent compound, 1-[2-hydroxy-3-[(4-hydroxy-3-nitrocoumarin-7-yl)oxy]propyl]-4- (4-chlorobenzyl)piperazine, 30, had a pA2 of 9.0 against histamine on guinea pig ileum and inhibited histamine release in the rat PPA test with a potency similar to that of disodium cromoglycate.

  DOI：

  10.1021/jm00377a013
• 作为产物：
  描述：

  ethyl 4-(4-chlorobenzyl)piperazine-1-carboxylate 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 乙二醇乙醚 、 溶剂黄146 、 氯苯 为溶剂， 反应 38.5h， 生成 7-[4-(4-Chloro-benzyl)-piperazin-1-ylmethyl]-4-hydroxy-chromen-2-one; hydrochloride
  参考文献：
  名称：

  N-Benzylpiperazino derivatives of 3-nitro-4-hydroxycoumarin with H1 antihistamine and mast cell stabilizing properties

  摘要：

  In a small range finding study a number of N-benzylpiperazino derivates of 3-nitro-4-hydroxycoumarin have been shown to combine potent H1-antihistamine activity with that of mast cell stabilization as demonstrated by their activity as antagonists of histamine on guinea pig ileum and by their inhibition of the release of histamine in rat passive peritoneal anaphylaxis (PPA). The most potent compound, 1-[2-hydroxy-3-[(4-hydroxy-3-nitrocoumarin-7-yl)oxy]propyl]-4- (4-chlorobenzyl)piperazine, 30, had a pA2 of 9.0 against histamine on guinea pig ileum and inhibited histamine release in the rat PPA test with a potency similar to that of disodium cromoglycate.

  DOI：

  10.1021/jm00377a013