1-benzylgalanthaminium bromide | 146504-29-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 1-benzylgalanthaminium bromide
• 英文别名: (1S,12S,14R)-4-benzyl-9-methoxy-4-methyl-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;bromide
• CAS: 146504-29-2
• 化学式: Br*C₂₄H₂₈NO₃
• 分子量: 458.395
• InChiKey: NBKHLZQVXQCDJC-KHSPWSTHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴甲苯 、 加兰他敏 以 乙醚 为溶剂， 反应 24.0h， 以82%的产率得到1-benzylgalanthaminium bromide
  参考文献：
  名称：

  Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease?

  摘要：

  We conducted structural and pharmacological studies of galanthamine, a cortical acetylcholinesterase (AChE) inhibitor, and 19 structural analogs. Systematic derivatization of galanthamine at the cyclohexene ring, tertiary amino, hydroxyl and methoxyl functions indicated that these structural features are essential for biological activity. Molecular modeling studies suggested that the low energy conformations of the analogs are similar to that of the parent. One derivative, galanthamine n-butyl carbamate, had an LD50 of over 100 mg/kg (ip) in mice. In a passive avoidance paradigm, this analog improved performance in a dose-dependent fashion with a peak effect at 0.1 mg/kg in control and 0.5 mg/kg in basal forebrain lesioned mice. In the same paradigm, the peak effect of the parent compound is a 6-fold higher dose. With this surprinsingly high therapeutic ratio, this compound may be of interest in treating cholinergic deficits of the central nervous system such as Alzheimer's disease.

  DOI：

  10.1016/0223-5234(92)90087-h