(E)-4-(2-(6-bromo-1H-benzimidazol-2-yl)ethenyl)-N,N-dimethylaniline | 1434175-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (E)-4-(2-(6-bromo-1H-benzimidazol-2-yl)ethenyl)-N,N-dimethylaniline
• 英文别名: (E)-4-[2-(6-bromo-1H-benzimidazol-2-yl)ethenyl]-N,N-dimethylaniline；4-[(E)-2-(6-bromo-1H-benzimidazol-2-yl)ethenyl]-N,N-dimethylaniline
• CAS: 1434175-82-2
• 化学式: C₁₇H₁₆BrN₃
• 分子量: 342.238
• InChiKey: SAYJTEDRXODGAU-BJMVGYQFSA-N

物化性质

• 沸点：
  547.8±60.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-(6-bromo-1H-benzimidazol-2-yl)ethenyl)-N,N-dimethylaniline 在 四(三苯基膦)钯 、 盐酸胍 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.0h， 生成 (E)-4-[2-(1-tert-butoxycarbonyl-6-tributylstannylbenzimidazol-2-yl)ethenyl]-N,N-dimethylaniline
  参考文献：
  名称：

  放射性ヨウ素標識スチリル置換芳香族ヘテロ環化合物

  摘要：

  通过核医学技术，提供一种能够非侵入性地成像生物体内Tau蛋白的新型Tau蛋白成像剂。本发明涉及一种放射性碘标记的苯基取代芳香族杂环化合物或其盐，或者包含该化合物的放射性药物，其由特定通用式表示。【选定图】无

  公开号：

  JP2016079108A
• 作为产物：
  描述：

  3-(4-dimethylamino-phenyl)-propenal 、 4-溴邻苯二胺 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86.7%的产率得到(E)-4-(2-(6-bromo-1H-benzimidazol-2-yl)ethenyl)-N,N-dimethylaniline
  参考文献：
  名称：

  Synthesis and biological evaluation of novel styryl benzimidazole derivatives as probes for imaging of neurofibrillary tangles in Alzheimer’s disease

  摘要：

  This paper describes the synthesis and biological evaluation of styrylbenzimidazole (SBIM) derivatives as agents for imaging neurofibrillary tangles (NFT) in patients with Alzheimer's disease (AD). SBIM derivatives were prepared with 4-iodobenzene-1,2-diamine and substituted cinnamaldehydes. In binding experiments using recombinant tau and A beta(1-42) aggregates, SBIM-3 showed higher affinity for the tau aggregates than Ab1-42 aggregates (ratio of K-d values was 2.73). In in vitro autoradiography and fluorescent staining, [I-125]SBIM-3 (or SBIM-3) bound NFT in sections of AD brain tissue. In biodistribution experiments using normal mice, all [I-125]SBIM derivatives showed high initial uptake into (3.20-4.11%ID/g at 2 min after the injection) and rapid clearance from (0.12-0.33%ID/g at 60 min after the injection) the brain. In conclusion, appropriate structural modifications of SBIM derivatives could lead to more useful agents for the in vivo imaging of NFT in AD brains. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.054

文献信息

• 放射性ヨウ素標識スチリル置換芳香族ヘテロ環化合物
  申请人：国立大学法人京都大学

  公开号：JP2016079108A

  公开（公告）日：2016-05-16

  【課題】核医学的手法により非侵襲的に生体内のタウ蛋白を画像化し得る、新規なタウタンパク質イメージング剤を提供する。【解決手段】本発明は、所定の一般式で表される放射性ヨウ素標識スチリル置換芳香族ヘテロ環化合物若しくはその塩、又はこれを含む放射性医薬に関する。【選択図】なし

  通过核医学技术，提供一种能够非侵入性地成像生物体内Tau蛋白的新型Tau蛋白成像剂。本发明涉及一种放射性碘标记的苯基取代芳香族杂环化合物或其盐，或者包含该化合物的放射性药物，其由特定通用式表示。【选定图】无
• Synthesis and biological evaluation of novel styryl benzimidazole derivatives as probes for imaging of neurofibrillary tangles in Alzheimer’s disease
  作者：Kenji Matsumura、Masahiro Ono、Masashi Yoshimura、Hiroyuki Kimura、Hiroyuki Watanabe、Yoko Okamoto、Masafumi Ihara、Ryosuke Takahashi、Hideo Saji

  DOI：10.1016/j.bmc.2013.02.054

  日期：2013.6

  This paper describes the synthesis and biological evaluation of styrylbenzimidazole (SBIM) derivatives as agents for imaging neurofibrillary tangles (NFT) in patients with Alzheimer's disease (AD). SBIM derivatives were prepared with 4-iodobenzene-1,2-diamine and substituted cinnamaldehydes. In binding experiments using recombinant tau and A beta(1-42) aggregates, SBIM-3 showed higher affinity for the tau aggregates than Ab1-42 aggregates (ratio of K-d values was 2.73). In in vitro autoradiography and fluorescent staining, [I-125]SBIM-3 (or SBIM-3) bound NFT in sections of AD brain tissue. In biodistribution experiments using normal mice, all [I-125]SBIM derivatives showed high initial uptake into (3.20-4.11%ID/g at 2 min after the injection) and rapid clearance from (0.12-0.33%ID/g at 60 min after the injection) the brain. In conclusion, appropriate structural modifications of SBIM derivatives could lead to more useful agents for the in vivo imaging of NFT in AD brains. (C) 2013 Elsevier Ltd. All rights reserved.