4-(7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)butan-1-amine | 1285549-08-7

• 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: 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)butan-1-amine
• CAS: 1285549-08-7
• 化学式: C₁₆H₂₆N₂O₂
• 分子量: 278.395
• InChiKey: KGICDVVRYHYYQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)butan-1-amine 、 5-bromo-2,3-dimethoxybenzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到5-bromo-N-(4-(7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)butyl)-2,3-dimethoxybenzamide
  参考文献：
  名称：

  Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

  摘要：

  5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2,3-dimethoxy-benzamide (1) is one of the most potent and selective sigma(2) receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their sigma(1)/sigma(2) binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher sigma(1)/sigma(2) selectivity, derived from a higher sigma(2) affinity and a lower sigma(1) affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional sigma(2) receptor binding affinity and selectivity for this active series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.006
• 作为产物：
  描述：

  7,8-dimethoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 在 硼烷四氢呋喃络合物 、 potassium carbonate 、 一水合肼 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)butan-1-amine
  参考文献：
  名称：

  Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

  摘要：

  5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2,3-dimethoxy-benzamide (1) is one of the most potent and selective sigma(2) receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their sigma(1)/sigma(2) binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher sigma(1)/sigma(2) selectivity, derived from a higher sigma(2) affinity and a lower sigma(1) affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional sigma(2) receptor binding affinity and selectivity for this active series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.006