(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 | 1131148-68-9

• 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,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
• CAS: 1131148-68-9
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: SADVNIYDNPHOAY-ODFWMOKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 (5Z)-5-[(2S,2aR,6-S,7aS,7bR,8R,9S)-hexahydro-7b-(N-methyl-N-allylaminomethyl)-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
• 作为产物：
  描述：

  (11Z)-1',2'-dihydroxystemofoline 在 sodium periodate 、 silica gel 作用下， 以 乙醚 、 氯仿 、 水 为溶剂， 生成 (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
  参考文献：
  名称：

  Stefofoline生物碱的半合成和生物活性

  摘要：

  所述的半合成百部生物碱（3' - [R）-stemofolenol（1），（3'小号）-stemofolenol（2），methylstemofoline（3），和（3'小号）-hydroxystemofoline（5 11）和非天然类似物（ë）-methylstemofoline（15）和3' - [R -hydroxystemofoline（11）已达到由（11 ž）-1'，2'- didehydrostemofoline（4）。该合成方法首次允许获得非对映体富集的1和2样品并在C-3'处分配其绝对配置。获得足够量的这些化合物以进行生物学测试。在作为AChE抑制剂的定量分析中，发现（11 Z）-1'，2'-二氢硬脂fo啉（4）和（3 'S）-羟基硬脂fo碱（5）最活跃。

  DOI：

  10.1021/np800806b

文献信息

• Semisynthesis and Acetylcholinesterase Inhibitory Activity of Stemofoline Alkaloids and Analogues
  作者：Kwankamol Sastraruji、Thanapat Sastraruji、Stephen G. Pyne、Alison T. Ung、Araya Jatisatienr、Wilford Lie

  DOI：10.1021/np100137h

  日期：2010.5.28

  Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.