(E)-1-(5-fluoro-1H-indol-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one | 1334545-59-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(5-fluoro-1H-indol-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(5-fluoroindol-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1334545-59-3
• 化学式: C₁₈H₁₄FNO₂
• 分子量: 295.313
• InChiKey: UEYIUEIBNPSQMF-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氟吲哚 、 (2E)-3-(4-甲氧基苯基)丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以67.8%的产率得到(E)-1-(5-fluoro-1H-indol-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Novel imaging agents for β-amyloid plaque based on the N-benzoylindole core

  摘要：

  We report the synthesis and evaluation of a series of N-benzoylindole derivatives as novel potential imaging agents for beta-amyloid plaques. In vitro binding studies using A beta(1-40) aggregates versus [I-125]TZDM showed that all these derivatives demonstrated high binding affinities (K-i values ranged from 8.4 to 121.6 nM). Moreover, two radioiodinated compounds [I-125]7 and [I-125]14 were prepared. Autoradiography for [I-125]14 displayed intense and specific labeling of A beta plaques in the brain sections of AD model mice (C57, APP/PS1) with low background. In vivo biodistribution in normal mice exhibited sufficient initial brain uptake for imaging (2.19% and 2.00% ID/g at 2 min postinjection for [I-125]7 and [I-125]14, respectively). Although additional modifications are necessary to improve brain uptake and clearance from the brain, the N-benzoylindole may be served as a backbone structure to develop novel beta-amyloid imaging probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.077

文献信息

• Novel imaging agents for β-amyloid plaque based on the N-benzoylindole core
  作者：Yang Yang、Xin-Hong Duan、Jun-Yuan Deng、Bing Jin、Hong-Mei Jia、Bo-Li Liu

  DOI：10.1016/j.bmcl.2011.06.077

  日期：2011.9

  We report the synthesis and evaluation of a series of N-benzoylindole derivatives as novel potential imaging agents for beta-amyloid plaques. In vitro binding studies using A beta(1-40) aggregates versus [I-125]TZDM showed that all these derivatives demonstrated high binding affinities (K-i values ranged from 8.4 to 121.6 nM). Moreover, two radioiodinated compounds [I-125]7 and [I-125]14 were prepared. Autoradiography for [I-125]14 displayed intense and specific labeling of A beta plaques in the brain sections of AD model mice (C57, APP/PS1) with low background. In vivo biodistribution in normal mice exhibited sufficient initial brain uptake for imaging (2.19% and 2.00% ID/g at 2 min postinjection for [I-125]7 and [I-125]14, respectively). Although additional modifications are necessary to improve brain uptake and clearance from the brain, the N-benzoylindole may be served as a backbone structure to develop novel beta-amyloid imaging probes. (C) 2011 Elsevier Ltd. All rights reserved.