(5-bromobenzofuran-2-yl)(4-(methylamino)phenyl)methanone | 1320336-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-bromobenzofuran-2-yl)(4-(methylamino)phenyl)methanone
• 英文别名: (5-Bromo-1-benzofuran-2-yl)-[4-(methylamino)phenyl]methanone
• CAS: 1320336-31-9
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 330.181
• InChiKey: FGKMRSSJZNQVJK-UHFFFAOYSA-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：
  0.06
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-bromobenzofuran-2-yl)(4-(methylamino)phenyl)methanone 在 四(三苯基膦)钯 、 六正丁基二锡 、 三乙胺 、 盐酸 、 sodium iodide 、 双氧水 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 10.25h， 生成 (5-(125I)iodanyl-1-benzofuran-2-yl)-[4-(methylamino)phenyl]methanone
  参考文献：
  名称：

  Synthesis and evaluation of benzofuran-2-yl(phenyl)methanone derivatives as ligands for β-amyloid plaques

  摘要：

  A series of benzofuran-2-yl(phenyl)methanone derivatives were synthesized and evaluated as novel probes for beta-amyloid plaques. These derivatives were produced by a Rap-Stoermer condensation reaction. Compounds with a N,N-dimethylamino group displayed high affinity for A beta(1-42) aggregates with K(i) values in the nanomolar range. Autoradiography with brain sections of AD model mice (APP/PS1) revealed that a radioiodinated probe, [(125)I]10, labeled beta-amyloid plaques selectively and displayed good brain uptake (3.53% ID/g) at 2 min. The results suggest that benzofuran-2-yl(phenyl) methanone derivatives should be investigated further as potential probes for detecting beta-amyloid plaques in the AD brain. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.049
• 作为产物：
  描述：

  (4-aminophenyl)(5-bromobenzofuran-2-yl)methanone 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以33%的产率得到(5-bromobenzofuran-2-yl)(4-(methylamino)phenyl)methanone
  参考文献：
  名称：

  Synthesis and evaluation of benzofuran-2-yl(phenyl)methanone derivatives as ligands for β-amyloid plaques

  摘要：

  A series of benzofuran-2-yl(phenyl)methanone derivatives were synthesized and evaluated as novel probes for beta-amyloid plaques. These derivatives were produced by a Rap-Stoermer condensation reaction. Compounds with a N,N-dimethylamino group displayed high affinity for A beta(1-42) aggregates with K(i) values in the nanomolar range. Autoradiography with brain sections of AD model mice (APP/PS1) revealed that a radioiodinated probe, [(125)I]10, labeled beta-amyloid plaques selectively and displayed good brain uptake (3.53% ID/g) at 2 min. The results suggest that benzofuran-2-yl(phenyl) methanone derivatives should be investigated further as potential probes for detecting beta-amyloid plaques in the AD brain. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.049

文献信息

• Synthesis and evaluation of benzofuran-2-yl(phenyl)methanone derivatives as ligands for β-amyloid plaques
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Boli Liu、Hideo Saji

  DOI：10.1016/j.bmc.2011.04.049

  日期：2011.7

  A series of benzofuran-2-yl(phenyl)methanone derivatives were synthesized and evaluated as novel probes for beta-amyloid plaques. These derivatives were produced by a Rap-Stoermer condensation reaction. Compounds with a N,N-dimethylamino group displayed high affinity for A beta(1-42) aggregates with K(i) values in the nanomolar range. Autoradiography with brain sections of AD model mice (APP/PS1) revealed that a radioiodinated probe, [(125)I]10, labeled beta-amyloid plaques selectively and displayed good brain uptake (3.53% ID/g) at 2 min. The results suggest that benzofuran-2-yl(phenyl) methanone derivatives should be investigated further as potential probes for detecting beta-amyloid plaques in the AD brain. (C) 2011 Elsevier Ltd. All rights reserved.