ethyl 5,11-dihydrodibenzo[b,e][1,4]oxazepine-3-carboxylate | 943783-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5,11-dihydrodibenzo[b,e][1,4]oxazepine-3-carboxylate
• 英文别名: Ethyl 6,11-dihydrobenzo[c][1,5]benzoxazepine-9-carboxylate
• CAS: 943783-52-6
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: PHZPKEFNSZIVOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5,11-dihydrodibenzo[b,e][1,4]oxazepine-3-carboxylate 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.09h， 生成
  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-溴-4-甲基苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 sodium formate 、 铁粉 、 铜 、 potassium carbonate 、 氯化铵 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 ethyl 5,11-dihydrodibenzo[b,e][1,4]oxazepine-3-carboxylate
  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