dimethylcarbamic acid 1-[2-(4-nitrophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl ester | 649722-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: dimethylcarbamic acid 1-[2-(4-nitrophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl ester
• CAS: 649722-77-0
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: OWIKWGLFSBRWSB-UHFFFAOYSA-N

物化性质

• 沸点：
  571.8±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.94
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 dimethylcarbamic acid 1-[2-(4-nitrophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl ester 在 甲酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 dimethylcarbamic acid 2-methyl-1-[2-(4-nitrophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl ester
  参考文献：
  名称：

  A conformational restriction approach to the development of dual inhibitors of acetylcholinesterase and serotonin transporter as potential agents for Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) has been treated with acetylcholinesterase (AChE) inhibitors such as donepezil. However, the clinical usefulness of AChE inhibitors is limited mainly due to their adverse peripheral effects. Depression seen in AD patients has been treated with serotonin transporter (SERT) inhibitors. We considered that combining SERT and AChE inhibition could improve the clinical usefulness of AChE inhibitors. In a previous paper, we found a potential dual inhibitor, 1, of AChE (IC50 = 101 nM) and SERT (IC50 = 42 nM), but its AChE inhibition activity was less than donepezil (IC50 = 10 nM). Here, we report the conformationally restricted (R)-18a considerably enhanced inhibitory activity against AChE (IC50 14 nM) and SERT (IC50 = 6 nM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00452-8
• 作为产物：
  描述：

  dimethylcarbamic acid 4-formyl-3-vinylphenyl ester 在 palladium on activated charcoal RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 锂硼氢 、 四溴化碳 、 四丁基氟化铵 、 氢气 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 40.83h， 生成 dimethylcarbamic acid 1-[2-(4-nitrophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl ester
  参考文献：
  名称：

  A conformational restriction approach to the development of dual inhibitors of acetylcholinesterase and serotonin transporter as potential agents for Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) has been treated with acetylcholinesterase (AChE) inhibitors such as donepezil. However, the clinical usefulness of AChE inhibitors is limited mainly due to their adverse peripheral effects. Depression seen in AD patients has been treated with serotonin transporter (SERT) inhibitors. We considered that combining SERT and AChE inhibition could improve the clinical usefulness of AChE inhibitors. In a previous paper, we found a potential dual inhibitor, 1, of AChE (IC50 = 101 nM) and SERT (IC50 = 42 nM), but its AChE inhibition activity was less than donepezil (IC50 = 10 nM). Here, we report the conformationally restricted (R)-18a considerably enhanced inhibitory activity against AChE (IC50 14 nM) and SERT (IC50 = 6 nM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00452-8