(1E,4E)-1-(4-bromophenyl)-5-(4-(dimethylamino)phenyl)penta-1,4-dien-3-one | 1285533-49-4

• 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: (1E,4E)-1-(4-bromophenyl)-5-(4-(dimethylamino)phenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-(4-bromophenyl)-5-[4-(dimethylamino)phenyl]penta-1,4-dien-3-one
• CAS: 1285533-49-4
• 化学式: C₁₉H₁₈BrNO
• 分子量: 356.262
• InChiKey: SZXMKYQCGVZYSD-FNCQTZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(4-bromophenyl)-5-(4-(dimethylamino)phenyl)penta-1,4-dien-3-one 在 四(三苯基膦)钯 、 三正丁基氢锡 、 盐酸 、 sodium iodide 、 双氧水 作用下， 以 甲苯 、 水 为溶剂， 反应 10.0h， 生成 (1E,4E)-1-[4-(dimethylamino)phenyl]-5-(4-(125I)iodanylphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of Novel Dibenzylideneacetone Derivatives as Probes for β-Amyloid Plaques

  摘要：

  A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A beta(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two F-18 fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity folr A beta(1-42) aggregates (K-i ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for beta-amyloid imaging probes.

  DOI：

  10.1021/jm101404k
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 (1E,4E)-1-(4-bromophenyl)-5-(4-(dimethylamino)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of Novel Dibenzylideneacetone Derivatives as Probes for β-Amyloid Plaques

  摘要：

  A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A beta(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two F-18 fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity folr A beta(1-42) aggregates (K-i ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for beta-amyloid imaging probes.

  DOI：

  10.1021/jm101404k

文献信息

• US4264710A
  申请人：——

  公开号：US4264710A

  公开（公告）日：1981-04-28
• US4259432A
  申请人：——

  公开号：US4259432A

  公开（公告）日：1981-03-31
• US4290870A
  申请人：——

  公开号：US4290870A

  公开（公告）日：1981-09-22
• US4367280A
  申请人：——

  公开号：US4367280A

  公开（公告）日：1983-01-04
• Synthesis and Structure−Affinity Relationships of Novel Dibenzylideneacetone Derivatives as Probes for β-Amyloid Plaques
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Boli Liu、Hideo Saji

  DOI：10.1021/jm101404k

  日期：2011.4.14

  A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A beta(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two F-18 fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity folr A beta(1-42) aggregates (K-i ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for beta-amyloid imaging probes.