6-bromo-4'-methylaminoflavone | 871101-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-bromo-4'-methylaminoflavone
• 英文别名: 6-bromo-2-[4-(methylamino)phenyl]chromen-4-one
• CAS: 871101-26-7
• 化学式: C₁₆H₁₂BrNO₂
• 分子量: 330.181
• InChiKey: YPJGQDBUZFMXEO-UHFFFAOYSA-N

物化性质

• 沸点：
  474.3±45.0 °C(Predicted)
• 密度：
  1.536±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-4'-methylaminoflavone 在 四(三苯基膦)钯 、 六正丁基二锡 、 三乙胺 、 碘 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 6.17h， 以20 mg的产率得到6-iodo-4'-methylaminoflavone
  参考文献：
  名称：

  Radioiodinated Flavones for in Vivo Imaging of β-Amyloid Plaques in the Brain

  摘要：

  In vivo imaging of beta-amyloid (A beta) peptide aggregates in the brain may lead to early detection of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of AD treatment. The purpose of this study was to develop novel amyloid imaging agents based on flavone as a core structure. Radioiodinated flavone derivatives were designed and synthesized. The binding affinities of flavone derivatives for A beta aggregates varied from 13 to 77 nM. When in vitro plaque labeling was carried out using post-mortem AD brain sections, all flavones intensely stained not only amyloid plaques but also cerebrovascular amyloids. In biodistribution studies using normal mice, they displayed high brain uptakes ranging from 3.2 to 4.1% ID/g at 2 min postinjection. The radioactivity washed out from the brain rapidly (0.5-1.9% ID/g at 30 min), which is highly desirable for amyloid imaging agents. The results in the study suggest that these classes of radioiodinated flavones may be useful candidates as potential imaging agents for amyloid plaques.

  DOI：

  10.1021/jm050635e
• 作为产物：
  描述：

  6-bromo-4'-aminoflavone 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 6-bromo-4'-methylaminoflavone
  参考文献：
  名称：

  Radioiodinated Flavones for in Vivo Imaging of β-Amyloid Plaques in the Brain

  摘要：

  In vivo imaging of beta-amyloid (A beta) peptide aggregates in the brain may lead to early detection of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of AD treatment. The purpose of this study was to develop novel amyloid imaging agents based on flavone as a core structure. Radioiodinated flavone derivatives were designed and synthesized. The binding affinities of flavone derivatives for A beta aggregates varied from 13 to 77 nM. When in vitro plaque labeling was carried out using post-mortem AD brain sections, all flavones intensely stained not only amyloid plaques but also cerebrovascular amyloids. In biodistribution studies using normal mice, they displayed high brain uptakes ranging from 3.2 to 4.1% ID/g at 2 min postinjection. The radioactivity washed out from the brain rapidly (0.5-1.9% ID/g at 30 min), which is highly desirable for amyloid imaging agents. The results in the study suggest that these classes of radioiodinated flavones may be useful candidates as potential imaging agents for amyloid plaques.

  DOI：

  10.1021/jm050635e
• 作为试剂：
  描述：

  sodium methoxide methanol 、 6-bromo-4'-aminoflavone 、 聚合甲醛 、 硼氢化钠 在 6-bromo-4'-methylaminoflavone 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以so as to obtain a product of interest, 6-bromo-4′-methylaminoflavone (compound 6)的产率得到6-bromo-4'-methylaminoflavone
  参考文献：
  名称：

  Composition For Diagnosing Amyloid-Related Diseases

  摘要：

  本发明提供了一种用于诊断淀粉样相关疾病的组合物，其中包括一种黄酮衍生物、一种查尔酮衍生物、一种苯乙烯基色酮衍生物或一种香豆素衍生物。这些化合物具有高结合特异性，能够与淀粉样β蛋白结合，具有高渗透性到血脑屏障，并能够迅速从除脑部老年斑以外的其他部位消失。因此，使用这些化合物的本发明组合物能够高精度地诊断淀粉样相关疾病。

  公开号：

  US20080131367A1

文献信息

• アミロイドβ疾患のホウ素中性子捕捉療法用化合物
  申请人：株式会社ＣＩＣＳ

  公开号：JP2020066619A

  公开（公告）日：2020-04-30

  【課題】アミロイドβ蛋白に対する高い結合特異性、高い血液脳関門の透過性、脳内老人斑内での貯留性を有し、一方、脳内老人斑以外の部位には残留しにくい特性を持つホウ素担体化合物を提供する。【解決手段】フラボン誘導体、クロモン誘導体、クマリン誘導体、オーロン誘導体、カルコン誘導体、ベンゾチアゾール誘導体及びスチルベン誘導体において、ホウ素−１０原子を各誘導体に含有するアミロイドβ又は病的アミロイド蛋白関連疾患に対するホウ素中性子捕捉療法用化合物及びその用途。【選択図】なし

  针对β淀粉样蛋白具有高结合特异性、高血脑屏障透过性和在脑内老年斑中具有积累性，同时具有不易残留在脑内老年斑以外部位的硼载体化合物。通过在类黄酮衍生物、香豆素衍生物、香豆素衍生物、噁罗衍生物、查尔酮衍生物、苯并噻唑衍生物和白藜芦醇衍生物中含有硼-10原子来提供用于β淀粉样或病理性淀粉样蛋白相关疾病的硼中子俘获疗法的化合物及其用途。【选择图】无
• Composition for diagnosing amyloid-related diseases
  申请人：Nagasaki University

  公开号：US08192717B2

  公开（公告）日：2012-06-05

  A composition for diagnosing amyloid-related diseases, which comprises a flavone derivative, a chalcone derivative, a styrylchromone derivative, or a coumarin derivative, is provided. These compounds have high binding specificity to an amyloid β protein, high permeability to a blood-brain barrier, and ability to rapidly disappear from sites other than cerebral senile plaque. Accordingly, the composition of the present invention using these compounds enables the diagnosis of amyloid-related diseases with high precision.

  本发明提供了一种用于诊断淀粉样相关疾病的组合物，包括黄酮衍生物、查尔酮衍生物、苯乙烯基香豆素衍生物或香豆素衍生物。这些化合物具有高度的结合特异性，能够与淀粉样β蛋白高度结合，具有高渗透性穿过血脑屏障，且能够迅速从除老年斑外的其他部位消失。因此，使用这些化合物的本发明组合物能够高精度地诊断淀粉样相关疾病。
• COMPOSITION FOR AMYLOID-ASSOCIATED DISEASE DIAGNOSIS
  申请人：Nagasaki University

  公开号：EP1815872A1

  公开（公告）日：2007-08-08

  A composition for diagnosing amyloid-related diseases, which comprises a flavone derivative, a chalcone derivative, a styrylchromone derivative, or a coumarin derivative, is provided. These compounds have high binding specificity to an amyloid β protein, high permeability to a blood-brain barrier, and ability to rapidly disappear from sites other than cerebral senile plaque. Accordingly, the composition of the present invention using these compounds enables the diagnosis of amyloid-related diseases with high precision.

  本研究提供了一种用于诊断淀粉样蛋白相关疾病的组合物，该组合物由黄酮衍生物、查尔酮衍生物、苯乙烯基色酮衍生物或香豆素衍生物组成。 这些化合物与淀粉样β蛋白的结合特异性高，对血脑屏障的渗透性高，能够从脑衰老斑块以外的部位迅速消失。 因此，使用这些化合物的本发明组合物能够高精度地诊断淀粉样蛋白相关疾病。
• EP1815872
  申请人：——

  公开号：——

  公开（公告）日：——
• US8192717B2
  申请人：——

  公开号：US8192717B2

  公开（公告）日：2012-06-05