(E)-4-[2-(6-iodo-1H-benzimidazol-2-yl)ethenyl]aniline | 1434175-66-2

• 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-iodo-1H-benzimidazol-2-yl)ethenyl]aniline
• 英文别名: 4-[(E)-2-(6-iodo-1H-benzimidazol-2-yl)ethenyl]aniline
• CAS: 1434175-66-2
• 化学式: C₁₅H₁₂IN₃
• 分子量: 361.185
• InChiKey: BMOJEFBWGAWJML-FPYGCLRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (E)-4-[2-(6-iodo-1H-benzimidazol-2-yl)ethenyl]aniline 在 sodium methylate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以69.8%的产率得到(E)-4-[2-(6-iodo-1H-benzimidazol-2-yl)ethenyl]-N-methylaniline
  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
• 作为产物：
  描述：

  对硝基肉桂醛 在 盐酸 、 sodium metabisulfite 、 铁粉 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (E)-4-[2-(6-iodo-1H-benzimidazol-2-yl)ethenyl]aniline
  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

• 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.