5-(3-(benzyloxy)propyl)-3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine | 943783-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 5-(3-(benzyloxy)propyl)-3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine
• 英文别名: 2-Bromo-11-(3-phenylmethoxypropyl)-5,6-dihydrobenzo[b][1]benzazepine
• CAS: 943783-19-5
• 化学式: C₂₄H₂₄BrNO
• 分子量: 422.365
• InChiKey: YVINSZAERCRTPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(3-(benzyloxy)propyl)-3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine 在 硫酸 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 mineral oil 为溶剂， 反应 14.34h， 生成 methyl 2-(5-(3-(benzyloxy)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-3-yl)acetate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of tricyclic carboxylic acids as novel anti-histamines

  摘要：

  A series of tricyclic carboxylic acids having 6-amino-pyrimidine-2,4(1H,3H)-dione with piperazino or homopiperazino moiety linked by propylene, were synthesized and evaluated for their affinity toward human histamine H(1) receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice, bioavailability in rats, and their anti-inflammatory activity in mice OVA-induced biphasic cutaneous reaction model. Among the compounds tested, dibenzoxazepine carboxylic acid 13b showed both histamine H(1) receptor antagonistic activity and anti-inflammatory activity in vivo. In addition, 13b exhibited low affinity toward alpha(1) receptor and low occupancy of H(1) receptor in the brain. It is therefore, believed that 13b is a potential candidate for development as 3rd generation anti-histamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.003
• 作为产物：
  描述：

  3-苄氧基溴丙烷 、 3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.17h， 以79%的产率得到5-(3-(benzyloxy)propyl)-3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of tricyclic carboxylic acids as novel anti-histamines

  摘要：

  A series of tricyclic carboxylic acids having 6-amino-pyrimidine-2,4(1H,3H)-dione with piperazino or homopiperazino moiety linked by propylene, were synthesized and evaluated for their affinity toward human histamine H(1) receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice, bioavailability in rats, and their anti-inflammatory activity in mice OVA-induced biphasic cutaneous reaction model. Among the compounds tested, dibenzoxazepine carboxylic acid 13b showed both histamine H(1) receptor antagonistic activity and anti-inflammatory activity in vivo. In addition, 13b exhibited low affinity toward alpha(1) receptor and low occupancy of H(1) receptor in the brain. It is therefore, believed that 13b is a potential candidate for development as 3rd generation anti-histamine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.003