2,2,2-trichloroethyl 4-(3-(2-(2-methoxy-2-oxoethyl)dibenzo[b,e]oxepin-11(6H)-ylidene)propyl)-piperazine-1-carboxylate | 943783-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 2,2,2-trichloroethyl 4-(3-(2-(2-methoxy-2-oxoethyl)dibenzo[b,e]oxepin-11(6H)-ylidene)propyl)-piperazine-1-carboxylate
• CAS: 943783-05-9
• 化学式: C₂₇H₂₉Cl₃N₂O₅
• 分子量: 567.897
• InChiKey: RCXYGXUCAGSORV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.31
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl 4-(3-(2-(2-methoxy-2-oxoethyl)dibenzo[b,e]oxepin-11(6H)-ylidene)propyl)-piperazine-1-carboxylate 在 溶剂黄146 、 锌 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.33h， 生成 methyl (Z)-2-(11-(3-(piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate 、 methyl (E)-2-(11-(3-(piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-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：

  methyl 2-(11-(3-(4-methylpiperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate 、 氯甲酸-2,2,2-三氯乙酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以67%的产率得到2,2,2-trichloroethyl 4-(3-(2-(2-methoxy-2-oxoethyl)dibenzo[b,e]oxepin-11(6H)-ylidene)propyl)-piperazine-1-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