3,4-didehydro-3-deoxygalanthamine | 31504-42-4

• 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: 3,4-didehydro-3-deoxygalanthamine
• 英文别名: 3,4-anhydrogalanthamine；6-methoxy-10-methyl-galanthama-1,3-diene；Anhydro Galantamine；(1S,12S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,13,15-pentaene
• CAS: 31504-42-4
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: HPWHKLZOMVLIBL-YOEHRIQHSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  386.3±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  表雪花莲胺碱 生成 3,4-didehydro-3-deoxygalanthamine
  参考文献：
  名称：

  鸟嘌呤的结构与生物合成

  摘要：

  已通过NO-二甲基化确定了酚类芳基科的生物碱chlidanthine的结构，得到（-）-加兰他敏甲硫醇，然后由（-）-加兰他敏经（-）-表没食子胺制得。已经确定了源自Pummerer酮的一对差向异构烯丙基醇的相对立体化学。描述了将这些醇与亚硫酰氯以及与三二甲基氨基膦和四氯化碳转化为烯丙基氯化物。Ch草中已观察到ti化的加兰他敏和那屈丁的生物合成转化为桔黄素。

  DOI：

  10.1039/j39700001224

文献信息

• Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease?
  作者：SY Han、JE Sweeney、ES Bachman、EJ Schweiger、G Forloni、JT Coyle、BM Davis、MM Joullié

  DOI：10.1016/0223-5234(92)90087-h

  日期：1992.10

  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.
• Structure and biosynthesis of chlidanthine
  作者：J. G. Bhandarkar、G. W. Kirby

  DOI：10.1039/j39700001224

  日期：——

  in turn prepared from (–)-galanthamine via(–)-epigalanthamine. The relative stereochemistry of the pair of epimeric, allylic alcohols derived from Pummerer's ketone has been determined. The conversion of these alcohols into allylic chlorides with thionyl chloride and with trisdimethylaminophosphine and carbon tetrachloride is described. Biosynthetic conversion of tritiated galanthamine and narwedine

  已通过NO-二甲基化确定了酚类芳基科的生物碱chlidanthine的结构，得到（-）-加兰他敏甲硫醇，然后由（-）-加兰他敏经（-）-表没食子胺制得。已经确定了源自Pummerer酮的一对差向异构烯丙基醇的相对立体化学。描述了将这些醇与亚硫酰氯以及与三二甲基氨基膦和四氯化碳转化为烯丙基氯化物。Ch草中已观察到ti化的加兰他敏和那屈丁的生物合成转化为桔黄素。