(E)-1-(4-chlorophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one | 1271278-64-8

• 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)-1-(4-chlorophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one
• CAS: 1271278-64-8
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: BHLLLQPAWDZCDV-KRXBUXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-吲哚甲醛 、 对氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以14.1%的产率得到(E)-1-(4-chlorophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of indole-chalcone derivatives as β-amyloid imaging probe

  摘要：

  A series of chaclone derivatives containing an indole moiety were evaluated in competitive binding assays with A beta(1-42) aggregates versus [I-125]IMPY. The affinity of these compounds ranged from 4.46 to > 1008 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of AD transgenic mice. The radioiodinated probe [I-125]-(E)-3-(1H-indol-5-yl)-1-(4-iodophenyl)prop-2-en-1-one, [I-125]4, was prepared and autoradiography in sections of brain tissue from an animal model of AD showed that it labeled A beta plaques specifically. However, experiments with normal mice indicated that [I-125]4 exhibited a low uptake into the brain in vivo (0.41% ID/g at 2 min). Additional chemical modifications of this indole-chalcone structure may lead to more useful imaging agents for detecting beta-amyloid plaques in the brains of AD patients. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.045

文献信息

• Synthesis and biological evaluation of indole-chalcone derivatives as β-amyloid imaging probe
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Bo Li Liu、Hideo Saji

  DOI：10.1016/j.bmcl.2010.12.045

  日期：2011.2

  A series of chaclone derivatives containing an indole moiety were evaluated in competitive binding assays with A beta(1-42) aggregates versus [I-125]IMPY. The affinity of these compounds ranged from 4.46 to > 1008 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of AD transgenic mice. The radioiodinated probe [I-125]-(E)-3-(1H-indol-5-yl)-1-(4-iodophenyl)prop-2-en-1-one, [I-125]4, was prepared and autoradiography in sections of brain tissue from an animal model of AD showed that it labeled A beta plaques specifically. However, experiments with normal mice indicated that [I-125]4 exhibited a low uptake into the brain in vivo (0.41% ID/g at 2 min). Additional chemical modifications of this indole-chalcone structure may lead to more useful imaging agents for detecting beta-amyloid plaques in the brains of AD patients. (C) 2010 Elsevier Ltd. All rights reserved.