(E)-3-(furan-3-yl)-1-(2-methylcyclohex-1-enyl)prop-2-en-1-one | 1423655-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-3-(furan-3-yl)-1-(2-methylcyclohex-1-enyl)prop-2-en-1-one
• 英文别名: (E)-3-(furan-3-yl)-1-(2-methylcyclohexen-1-yl)prop-2-en-1-one
• CAS: 1423655-19-9
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: AZNDLDKOBWMDQO-VOTSOKGWSA-N

物化性质

• 沸点：
  345.7±31.0 °C(predicted)
• 密度：
  1.088±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(furan-3-yl)-1-(2-methylcyclohex-1-enyl)prop-2-en-1-one 在 甲酸 、 磷酸 、 5%-palladium/activated carbon 、 氢气 、 氧气 、 sodium hydride 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -25.0~75.0 ℃ 、303.99 kPa 条件下， 反应 77.33h， 生成 3-(furan-3-yl)-7a-hydroxy-3a-methyloctahydro-1H-inden-1-one
  参考文献：
  名称：

  Natural products inspired synthesis of neuroprotective agents against H2O2-induced cell death

  摘要：

  Stroke is a debilitating disease and the third leading cause of death in the USA, where over 2000 new stroke cases are diagnosed every day. Treatment options for stroke-related brain damage are very limited and there is an urgent need for effective neuroprotective agents to treat these conditions. Comparison of the structures of several classes of neuroprotective natural products such as limonoids and cardiac glycosides revealed the presence of a common structural motif which may account for their observed neuroprotective activity. Several natural product mimics that incorporate this shared structural motif were synthesized and were found to possess significant neuroprotective activity. These compounds enhanced cell viability against H2O2 induced oxidative stress or cell death in PC12 neuronal cells. The compounds were also found to enhance and modulate Na+/K+-ATPase activity of PC12 cells, which may suggest that the observed neuroprotective activity is mediated, at least partly, through interaction with Na+/K+-ATPase. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.013
• 作为产物：
  描述：

  3-糠醛 、 3-甲基-1-环己烯 、 乙酸酐 在 sodium hydroxide 、 zinc(II) iodide 、 zinc(II) chloride 、 对甲苯磺酸 作用下， 以 苯 、 乙醇 为溶剂， 反应 24.25h， 以65%的产率得到(E)-3-(furan-3-yl)-1-(2-methylcyclohex-1-enyl)prop-2-en-1-one
  参考文献：
  名称：

  Natural products inspired synthesis of neuroprotective agents against H2O2-induced cell death

  摘要：

  Stroke is a debilitating disease and the third leading cause of death in the USA, where over 2000 new stroke cases are diagnosed every day. Treatment options for stroke-related brain damage are very limited and there is an urgent need for effective neuroprotective agents to treat these conditions. Comparison of the structures of several classes of neuroprotective natural products such as limonoids and cardiac glycosides revealed the presence of a common structural motif which may account for their observed neuroprotective activity. Several natural product mimics that incorporate this shared structural motif were synthesized and were found to possess significant neuroprotective activity. These compounds enhanced cell viability against H2O2 induced oxidative stress or cell death in PC12 neuronal cells. The compounds were also found to enhance and modulate Na+/K+-ATPase activity of PC12 cells, which may suggest that the observed neuroprotective activity is mediated, at least partly, through interaction with Na+/K+-ATPase. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.013

文献信息

• Natural products inspired synthesis of neuroprotective agents against H2O2-induced cell death
  作者：Jehad Almaliti、Shadia E. Nada、Bryaune Carter、Zahoor A. Shah、L.M. Viranga Tillekeratne

  DOI：10.1016/j.bmcl.2013.01.013

  日期：2013.3

  Stroke is a debilitating disease and the third leading cause of death in the USA, where over 2000 new stroke cases are diagnosed every day. Treatment options for stroke-related brain damage are very limited and there is an urgent need for effective neuroprotective agents to treat these conditions. Comparison of the structures of several classes of neuroprotective natural products such as limonoids and cardiac glycosides revealed the presence of a common structural motif which may account for their observed neuroprotective activity. Several natural product mimics that incorporate this shared structural motif were synthesized and were found to possess significant neuroprotective activity. These compounds enhanced cell viability against H2O2 induced oxidative stress or cell death in PC12 neuronal cells. The compounds were also found to enhance and modulate Na+/K+-ATPase activity of PC12 cells, which may suggest that the observed neuroprotective activity is mediated, at least partly, through interaction with Na+/K+-ATPase. (c) 2013 Elsevier Ltd. All rights reserved.