(5Z)-5-[(2S,2aR,6S,7aS,7bR,8R,9S)-hexahydro-7b-[[[[(1,1-dimethylethoxy)carbonyl]amino][[(1,1-dimethylethoxy)carbonyl]imino]methylamino]methyl]-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone | 1392428-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5Z)-5-[(2S,2aR,6S,7aS,7bR,8R,9S)-hexahydro-7b-[[[[(1,1-dimethylethoxy)carbonyl]amino][[(1,1-dimethylethoxy)carbonyl]imino]methylamino]methyl]-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone
• CAS: 1392428-19-1
• 化学式: C₃₁H₄₄N₄O₉
• 分子量: 616.712
• InChiKey: JGBGXVRJDMXRNT-CFTNMMAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  44.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  137.46
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (5Z)-5-[(2S,2aR,6S,7aS,7bR,8R,9S)-hexahydro-7b-[[[[(1,1-dimethylethoxy)carbonyl]amino][[(1,1-dimethylethoxy)carbonyl]imino]methylamino]methyl]-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 3.0h， 以52%的产率得到(5Z)-5-[(2S,2aR,6S,7aS,7bR,8R,9S)-hexahydro-7b-[[(aminoiminomethyl)methylamino]methyl]-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone hydrochloride
  参考文献：
  名称：

  Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

  摘要：

  Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.047
• 作为产物：
  描述：

  (5Z)-5-[(2S,2aR,6S,7aS,7bS,8R,9S)-7b-(1E)-1-formylhexahydro-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (5Z)-5-[(2S,2aR,6S,7aS,7bR,8R,9S)-hexahydro-7b-[[[[(1,1-dimethylethoxy)carbonyl]amino][[(1,1-dimethylethoxy)carbonyl]imino]methylamino]methyl]-9-methyl-4H-2,2,6-(epoxy[1]propanyl[3]ylidene)furo[2,3,4-gh]pyrrolizin-10-ylidene]-4-methoxy-3-methyl-2(5H)-furanone
  参考文献：
  名称：

  Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

  摘要：

  Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.047