(E)-3-(4-(dimethylamino)phenyl)-1-(4-(((E)-3-(tributylstannyl)allyl)oxy)phenyl) prop-2-en-1-one | 1607465-93-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-(dimethylamino)phenyl)-1-(4-(((E)-3-(tributylstannyl)allyl)oxy)phenyl) prop-2-en-1-one
• CAS: 1607465-93-9
• 化学式: C₃₂H₄₇NO₂Sn
• 分子量: 596.441
• InChiKey: MSBKQVNHVLTBAL-GQMNMFPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  36.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(dimethylamino)phenyl)-1-(4-(((E)-3-(tributylstannyl)allyl)oxy)phenyl) prop-2-en-1-one 在 盐酸 、 sodium iodide 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 0.05h， 生成 (E)-3-[4-(dimethylamino)phenyl]-1-[4-[(E)-3-(125I)iodanylprop-2-enoxy]phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and evaluation of ethyleneoxylated and allyloxylated chalcone derivatives for imaging of amyloid β plaques by SPECT

  摘要：

  We report radioiodinated chalcone derivatives as new SPECT imaging probes for amyloid beta (A beta) plaques. The monoethyleneoxy derivative 2 and allyloxy derivative 8 showed a high affinity for A beta(1-42) aggregates with K-i values of 24 and 4.5 nM, respectively. Fluorescent imaging demonstrated that 2 and 8 clearly stained thioflavin-S positive A beta plaques in the brain sections of Tg2576 transgenic mice. In vitro autoradiography revealed that [I-125]2 displayed no clear accumulation toward A beta plaques in the brain sections of Tg2576 mice, whereas the accumulation pattern of [I-125]8 matched with the presence of A beta plaques both in the brain sections of Tg2576 mice and an AD patient. In biodistribution studies using normal mice, [I-125]2 showed preferable in vivo pharmacokinetics (4.82%ID/g at 2 min and 0.45%ID/g at 60 min), while [I-125]8 showed only a modest brain uptake (1.62%ID/g at 2 min) with slow clearance (0.56%ID/g at 60 min). [I-125]8 showed prospective binding properties for A beta plaques, although further structural modifications are needed to improve the blood brain barrier permeability and washout from brain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.032
• 作为产物：
  描述：

  (Z)-3-(三丁基甲锡烷基)烯丙基4-甲基苯磺酸酯 、 (E)-3-(4-(dimethylamino)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以45%的产率得到(E)-3-(4-(dimethylamino)phenyl)-1-(4-(((E)-3-(tributylstannyl)allyl)oxy)phenyl) prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and evaluation of ethyleneoxylated and allyloxylated chalcone derivatives for imaging of amyloid β plaques by SPECT

  摘要：

  We report radioiodinated chalcone derivatives as new SPECT imaging probes for amyloid beta (A beta) plaques. The monoethyleneoxy derivative 2 and allyloxy derivative 8 showed a high affinity for A beta(1-42) aggregates with K-i values of 24 and 4.5 nM, respectively. Fluorescent imaging demonstrated that 2 and 8 clearly stained thioflavin-S positive A beta plaques in the brain sections of Tg2576 transgenic mice. In vitro autoradiography revealed that [I-125]2 displayed no clear accumulation toward A beta plaques in the brain sections of Tg2576 mice, whereas the accumulation pattern of [I-125]8 matched with the presence of A beta plaques both in the brain sections of Tg2576 mice and an AD patient. In biodistribution studies using normal mice, [I-125]2 showed preferable in vivo pharmacokinetics (4.82%ID/g at 2 min and 0.45%ID/g at 60 min), while [I-125]8 showed only a modest brain uptake (1.62%ID/g at 2 min) with slow clearance (0.56%ID/g at 60 min). [I-125]8 showed prospective binding properties for A beta plaques, although further structural modifications are needed to improve the blood brain barrier permeability and washout from brain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.032