6-O-demethyl-6-O-(10'-phthalimidodecyl)-galanthamine | 187796-07-2

• 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: 6-O-demethyl-6-O-(10'-phthalimidodecyl)-galanthamine
• 英文别名: 2-(10-{[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-9-yl]oxy}decyl)-2,3-dihydro-1H-isoindole-1,3-dione；2-[10-[[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-9-yl]oxy]decyl]isoindole-1,3-dione
• CAS: 187796-07-2
• 化学式: C₃₄H₄₂N₂O₅
• 分子量: 558.718
• InChiKey: NHPLNKJBBLFCJG-FNMAWYSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-demethyl-6-O-(10'-phthalimidodecyl)-galanthamine 在 氢溴酸 、 碘 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以56%的产率得到9-dehydro-6-O-demethyl-6-O-(10'-phthalimidodecyl)-galanthaminium bromide
  参考文献：
  名称：

  Potent acetylcholinesterase inhibitors: design, synthesis, and structure–Activity relationships of bis-interacting ligands in the galanthamine series

  摘要：

  New galanthamine derivatives, especially bis-interacting ligands 3-5 and 7-9 were prepared in order to interact with the catalytic and the peripheral sites of acetylcholinesterase (AChE). The synthesis, the anticholinesterase activities, and the structure-activity relationships of bis-interacting ligands are reported. Compounds 4d-e were found to be more potent than galanthamine and tacrine in inhibiting AChE. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00133-3
• 作为产物：
  描述：

  加兰他敏 在 L-Selectride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 6-O-demethyl-6-O-(10'-phthalimidodecyl)-galanthamine
  参考文献：
  名称：

  Potent acetylcholinesterase inhibitors: design, synthesis, and structure–Activity relationships of bis-interacting ligands in the galanthamine series

  摘要：

  New galanthamine derivatives, especially bis-interacting ligands 3-5 and 7-9 were prepared in order to interact with the catalytic and the peripheral sites of acetylcholinesterase (AChE). The synthesis, the anticholinesterase activities, and the structure-activity relationships of bis-interacting ligands are reported. Compounds 4d-e were found to be more potent than galanthamine and tacrine in inhibiting AChE. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00133-3