5-bromo-2-(4-aminophenyl)benzofuran | 28718-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-bromo-2-(4-aminophenyl)benzofuran
• 英文别名: 4-(5-Bromo-1-benzofuran-2-yl)aniline
• CAS: 28718-77-6
• 化学式: C₁₄H₁₀BrNO
• 分子量: 288.143
• InChiKey: YCIJKCOLDBIXOX-UHFFFAOYSA-N

物化性质

• 沸点：
  421.5±30.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-aminophenyl)benzofuran 在 四(三苯基膦)钯 、 碘 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 氯仿 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 4-(5-iodobenzofuran-2-yl)-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)aniline
  参考文献：
  名称：

  Development of Radioiodinated Benzofuran Derivatives for in Vivo Imaging of Prion Deposits in the Brain

  摘要：

  Prion diseases are fatal neurodegenerative disorders associated with the deposition of abnormal prion protein aggregates (PrPSc) in the brain tissue. Here, we report the development of I-125-labeled iodobenzofuran (IBF) derivatives as single photon emission computed tomography (SPECT) imaging probes to detect cerebral PrPSc deposits. We synthesized and radioiodinated several 5-IBF and 6-IBF derivatives. The IBF derivatives were evaluated as prion imaging probes using recombinant mouse prion protein (rMoPrP) aggregates and brain sections of mouse-adapted bovine spongiform encephalopathy (mBSE)-infected mice. Although all the IBF derivatives were strongly adsorbed on the rMoPrP aggregates, [I-125]5-IBF-NHMe displayed the highest adsorption rate and potent binding affinity with an equilibrium dissociation constant (K-d) of 12.3 nM. Fluorescence imaging using IBF-NHMe showed clear signals of the PrPSc-positive amyloid deposits in the mBSE-infected mouse brains. Biodistribution studies in normal mice demonstrated slow uptake and clearance from the brain of I-125-IBF derivatives. Among the derivatives, [I-125]6-IBF-NH2 showed the highest peak brain uptake [2.59% injected dose (ID)/g at 10 min] and good clearance (0.51% ID/g at 180 min). Although the brain distribution of IBF derivatives should still be optimized for in vivo imaging, these compounds showed prospective binding properties to PrPSc. Further chemical modification of these IBF derivatives may contribute to the discovery of clinically applicable prion imaging probes.

  DOI：

  10.1021/acsinfecdis.8b00184
• 作为产物：
  描述：

  5-bromo-2-(4-nitrophenyl)benzofuran 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以20%的产率得到5-bromo-2-(4-aminophenyl)benzofuran
  参考文献：
  名称：

  Development of Radioiodinated Benzofuran Derivatives for in Vivo Imaging of Prion Deposits in the Brain

  摘要：

  Prion diseases are fatal neurodegenerative disorders associated with the deposition of abnormal prion protein aggregates (PrPSc) in the brain tissue. Here, we report the development of I-125-labeled iodobenzofuran (IBF) derivatives as single photon emission computed tomography (SPECT) imaging probes to detect cerebral PrPSc deposits. We synthesized and radioiodinated several 5-IBF and 6-IBF derivatives. The IBF derivatives were evaluated as prion imaging probes using recombinant mouse prion protein (rMoPrP) aggregates and brain sections of mouse-adapted bovine spongiform encephalopathy (mBSE)-infected mice. Although all the IBF derivatives were strongly adsorbed on the rMoPrP aggregates, [I-125]5-IBF-NHMe displayed the highest adsorption rate and potent binding affinity with an equilibrium dissociation constant (K-d) of 12.3 nM. Fluorescence imaging using IBF-NHMe showed clear signals of the PrPSc-positive amyloid deposits in the mBSE-infected mouse brains. Biodistribution studies in normal mice demonstrated slow uptake and clearance from the brain of I-125-IBF derivatives. Among the derivatives, [I-125]6-IBF-NH2 showed the highest peak brain uptake [2.59% injected dose (ID)/g at 10 min] and good clearance (0.51% ID/g at 180 min). Although the brain distribution of IBF derivatives should still be optimized for in vivo imaging, these compounds showed prospective binding properties to PrPSc. Further chemical modification of these IBF derivatives may contribute to the discovery of clinically applicable prion imaging probes.

  DOI：

  10.1021/acsinfecdis.8b00184

文献信息

• Synthesen antimikrobieller biskationischer 2-(Phenoxyphenyl)-indole und -1-benzofurane
  作者：Otto Dann、Jürgen Ruff、Hans-Peter Wolff、Helmut Grießmeier

  DOI：10.1002/jlac.198419840302

  日期：1984.3.12

  Zehn 2-(phenoxyphenyl)indole und vier 2-(Phenoxyphenyl)-1-benzofurane mit endständigen Amidinium- oder Imidazolinium-Gruppen wurden im Hinblick auf wachstumshemmende Eigenschaften synthetisiert.

  为了抑制生长，合成了具有末端am基或咪唑啉基的十个2-（苯氧基苯基）吲哚和四个2-（苯氧基苯基）-1-苯并呋喃。
• DANN, O.;RUFF, J.;WOLFF, H. -P.;GRIESSMEIER, H., LIEBIGS ANN. CHEM., 1984, N 3, 409-425
  作者：DANN, O.、RUFF, J.、WOLFF, H. -P.、GRIESSMEIER, H.

  DOI：——

  日期：——
• Development of Radioiodinated Benzofuran Derivatives for <i>in Vivo</i> Imaging of Prion Deposits in the Brain
  作者：Takeshi Fuchigami、Masao Kawasaki、Ryusuke Koyama、Mari Nakaie、Takehiro Nakagaki、Kazunori Sano、Ryuichiro Atarashi、Sakura Yoshida、Mamoru Haratake、Masahiro Ono、Noriyuki Nishida、Morio Nakayama

  DOI：10.1021/acsinfecdis.8b00184

  日期：2019.12.13

  Prion diseases are fatal neurodegenerative disorders associated with the deposition of abnormal prion protein aggregates (PrPSc) in the brain tissue. Here, we report the development of I-125-labeled iodobenzofuran (IBF) derivatives as single photon emission computed tomography (SPECT) imaging probes to detect cerebral PrPSc deposits. We synthesized and radioiodinated several 5-IBF and 6-IBF derivatives. The IBF derivatives were evaluated as prion imaging probes using recombinant mouse prion protein (rMoPrP) aggregates and brain sections of mouse-adapted bovine spongiform encephalopathy (mBSE)-infected mice. Although all the IBF derivatives were strongly adsorbed on the rMoPrP aggregates, [I-125]5-IBF-NHMe displayed the highest adsorption rate and potent binding affinity with an equilibrium dissociation constant (K-d) of 12.3 nM. Fluorescence imaging using IBF-NHMe showed clear signals of the PrPSc-positive amyloid deposits in the mBSE-infected mouse brains. Biodistribution studies in normal mice demonstrated slow uptake and clearance from the brain of I-125-IBF derivatives. Among the derivatives, [I-125]6-IBF-NH2 showed the highest peak brain uptake [2.59% injected dose (ID)/g at 10 min] and good clearance (0.51% ID/g at 180 min). Although the brain distribution of IBF derivatives should still be optimized for in vivo imaging, these compounds showed prospective binding properties to PrPSc. Further chemical modification of these IBF derivatives may contribute to the discovery of clinically applicable prion imaging probes.