2-(2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dienyl)-4H-chromen-4-ylidene)malononitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dienyl)-4H-chromen-4-ylidene)malononitrile
• 英文别名: 2-[2-[(1E,3E)-4-[4-(dimethylamino)phenyl]buta-1,3-dienyl]chromen-4-ylidene]propanedinitrile
• 化学式: C₂₄H₁₉N₃O
• 分子量: 365.434
• InChiKey: LYIZQEXBNOCQBT-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-METHYL-4H-CHROMEN-4-YLIDENE)MALONONITRILE聽 、 3-(4-dimethylamino-phenyl)-propenal 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以26.6%的产率得到2-(2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dienyl)-4H-chromen-4-ylidene)malononitrile
  参考文献：
  名称：

  Synthesis and evaluation of styrylpyran fluorophores for noninvasive detection of cerebral β-amyloid deposits

  摘要：

  The development of amyloid-specific fluorophores allows the visualization of cerebral beta-amyloid deposits using optical imaging technology. In the present study, a series of smart styrylpyran fluorophores with compact donor-acceptor architecture were designed and evaluated for noninvasive detection of cerebral beta-amyloid deposits. Spectral behavior of the fluorophores changed significantly (optical turn-on) upon binding to beta-amyloid aggregates. Computational studies were conducted to correlate the experimental K-d values with calculated binding energies, speculating the relationship between fluorophore structure and beta-amyloid affinity. In vivo studies demonstrated that PAD-2 could discriminate APP/PS1 transgenic mice from wild type controls, with specific labeling of cerebral beta-amyloid deposits confirmed by ex vivo observation. Collectively, these styrylpyran fluorophores could provide a new scaffold for the development of optical imaging probes targeting cerebral beta-amyloid deposits. (c) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2016.01.004

文献信息

• Synthesis and evaluation of styrylpyran fluorophores for noninvasive detection of cerebral β-amyloid deposits
  作者：Bi-yue Zhu、Yan Cheng、Guo-bo Li、Sheng-yong Yang、Zhi-rong Zhang

  DOI：10.1016/j.bmc.2016.01.004

  日期：2016.2

  The development of amyloid-specific fluorophores allows the visualization of cerebral beta-amyloid deposits using optical imaging technology. In the present study, a series of smart styrylpyran fluorophores with compact donor-acceptor architecture were designed and evaluated for noninvasive detection of cerebral beta-amyloid deposits. Spectral behavior of the fluorophores changed significantly (optical turn-on) upon binding to beta-amyloid aggregates. Computational studies were conducted to correlate the experimental K-d values with calculated binding energies, speculating the relationship between fluorophore structure and beta-amyloid affinity. In vivo studies demonstrated that PAD-2 could discriminate APP/PS1 transgenic mice from wild type controls, with specific labeling of cerebral beta-amyloid deposits confirmed by ex vivo observation. Collectively, these styrylpyran fluorophores could provide a new scaffold for the development of optical imaging probes targeting cerebral beta-amyloid deposits. (c) 2016 Published by Elsevier Ltd.