3-[4-(2-Chloro-benzyl)-piperazin-1-yl]-propan-1-ol | 79837-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[4-(2-Chloro-benzyl)-piperazin-1-yl]-propan-1-ol
• 英文别名: 3-[4-[(2-Chlorophenyl)methyl]piperazin-1-yl]propan-1-ol
• CAS: 79837-44-8
• 化学式: C₁₄H₂₁ClN₂O
• 分子量: 268.787
• InChiKey: NGVKQPYVMPXHPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4-(2-Chloro-benzyl)-piperazin-1-yl]-propan-1-ol 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 25.5h， 生成 6-{3-[4-(2-Chloro-benzyl)-piperazin-1-yl]-propoxy}-5-methyl-1H-4-oxa-1,2,3-triaza-cyclopenta[b]naphthalen-9-one; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties

  摘要：

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.

  DOI：

  10.1021/jm00161a022
• 作为产物：
  描述：

  1-(2-氯苄基)哌嗪 、 3-溴-1-丙醇 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 生成 3-[4-(2-Chloro-benzyl)-piperazin-1-yl]-propan-1-ol
  参考文献：
  名称：

  Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties

  摘要：

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.

  DOI：

  10.1021/jm00161a022

文献信息

• Benzopyrano (2,3-d) triazole-derivatives, their preparation and use in pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0034004B1

  公开（公告）日：1983-09-28
• Naphthotriazole derivatives, process for their preparation,intermediates and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0039552B1

  公开（公告）日：1983-09-21
• US4378360A
  申请人：——

  公开号：US4378360A

  公开（公告）日：1983-03-29
• US4405620A
  申请人：——

  公开号：US4405620A

  公开（公告）日：1983-09-20
• Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties
  作者：Derek R. Buckle、Caroline J. M. Rockell、Harry Smith、Barbara A. Spicer

  DOI：10.1021/jm00161a022

  日期：1986.11

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.