(E)-3-(1H-indol-5-yl)-1-(6-methoxynaphthalen-2-yl)prop-2-en-1-one

• 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-(1H-indol-5-yl)-1-(6-methoxynaphthalen-2-yl)prop-2-en-1-one
• 化学式: C₁₇H₉ClF₃O₃Pol
• 分子量: 327.4
• InChiKey: QSTKYNOOEBWKTK-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(1H-indol-5-yl)-1-(6-methoxynaphthalen-2-yl)prop-2-en-1-one 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 6-chloro-8-phenyl-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid
  参考文献：
  名称：

  Structure-based parallel medicinal chemistry approach to improve metabolic stability of benzopyran COX-2 inhibitors

  摘要：

  Combination of the structure-based design and solid-phase parallel synthesis provided an integrated approach to rapidly develop the structure-activity relationship of benzopyran COX-2 inhibitors. Binding free energies predicted by free energy perturbation theory yielded good agreement with experimental results. New potent and selective lead compounds with improved metabolic properties were identified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.023
• 作为产物：
  描述：

  5-吲哚甲醛 、 6-甲氧基-2-乙酰萘 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以40.8%的产率得到(E)-3-(1H-indol-5-yl)-1-(6-methoxynaphthalen-2-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