(E)-3-(3-bromo-4-dimethylamino-benzylidene)-6-bromochroman-4-one | 1584546-66-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: (E)-3-(3-bromo-4-dimethylamino-benzylidene)-6-bromochroman-4-one
• 英文别名: (3E)-6-bromo-3-[[3-bromo-4-(dimethylamino)phenyl]methylidene]chromen-4-one
• CAS: 1584546-66-6
• 化学式: C₁₈H₁₅Br₂NO₂
• 分子量: 437.131
• InChiKey: HZPPDIUDKMBPLZ-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-溴-4-二氢色原酮 、 3-溴-4-(二甲基氨基)苯甲醛 在 亚磷酸 作用下， 反应 8.0h， 以71%的产率得到(E)-3-(3-bromo-4-dimethylamino-benzylidene)-6-bromochroman-4-one
  参考文献：
  名称：

  Homoisoflavonoids as potential imaging agents for β-amyloid plaques in Alzheimer's disease

  摘要：

  A series of homoisoflavonoids [(E)-3-benzylidenechroman-4-ones, 3a-I] as novel potential diagnostic imaging agents targeting beta-amyloid (A beta) plaques in Alzheimer's disease (AD) were synthesized and evaluated. In vitro binding studies using A beta(1-40) aggregates with [I-125]IMPY as the reference ligand showed that these compounds demonstrated high to low binding affinities at the K-i values ranged from 9.10 to 432.03 nM, depending on the substitution of the phenyl ring. Fluorescent staining in vitro indicated that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of postmortem AD patients. Biodistribution studies in normal mice after i.v. injection of the radioiodinated homoisoflavonoid displayed good initial brain uptake (2.61% ID/g at 2 min post-injection) and rapid clearance from the brain (0.18% ID/g at 60 min), which is desirable for amyloid imaging agents. The results strongly suggest that these derivatives are worthy of further study and may be useful amyloid imaging agents for early detection of amyloid plaques in the brain of AD. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.020

文献信息

• Homoisoflavonoids as potential imaging agents for β-amyloid plaques in Alzheimer's disease
  作者：Changsheng Gan、Zhenzhen Zhao、Dou-Dou Nan、Binbin Yin、Jingyi Hu

  DOI：10.1016/j.ejmech.2014.02.020

  日期：2014.4

  A series of homoisoflavonoids [(E)-3-benzylidenechroman-4-ones, 3a-I] as novel potential diagnostic imaging agents targeting beta-amyloid (A beta) plaques in Alzheimer's disease (AD) were synthesized and evaluated. In vitro binding studies using A beta(1-40) aggregates with [I-125]IMPY as the reference ligand showed that these compounds demonstrated high to low binding affinities at the K-i values ranged from 9.10 to 432.03 nM, depending on the substitution of the phenyl ring. Fluorescent staining in vitro indicated that one compound with a N,N-dimethylamino group intensely stained A beta plaques within brain sections of postmortem AD patients. Biodistribution studies in normal mice after i.v. injection of the radioiodinated homoisoflavonoid displayed good initial brain uptake (2.61% ID/g at 2 min post-injection) and rapid clearance from the brain (0.18% ID/g at 60 min), which is desirable for amyloid imaging agents. The results strongly suggest that these derivatives are worthy of further study and may be useful amyloid imaging agents for early detection of amyloid plaques in the brain of AD. (C) 2014 Elsevier Masson SAS. All rights reserved.