methyl 5-[(E)-2-[3-bromo-4-[(E)-2-(4-methoxy-3-methoxycarbonylphenyl)(113C)ethenyl]phenyl](213C)ethenyl]-2-methoxybenzoate | 760988-01-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 5-[(E)-2-[3-bromo-4-[(E)-2-(4-methoxy-3-methoxycarbonylphenyl)(113C)ethenyl]phenyl](213C)ethenyl]-2-methoxybenzoate
• CAS: 760988-01-0
• 化学式: C₂₈H₂₅BrO₆
• 分子量: 539.385
• InChiKey: PGRBRJBIZXCXBC-FKXVIFASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-[(E)-2-[3-bromo-4-[(E)-2-(4-methoxy-3-methoxycarbonylphenyl)(113C)ethenyl]phenyl](213C)ethenyl]-2-methoxybenzoate 在 氢氧化钾 、 三溴化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 5-[(E)-2-[3-bromo-4-[(E)-2-(3-carboxy-4-hydroxyphenyl)(113C)ethenyl]phenyl](213C)ethenyl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  Fluoro-substituted and 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques

  摘要：

  Two styrylbenzene derivatives, (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB) and (EE)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha,alpha'-C-13(2) ([C-13]BSB), were synthesized for use as a histochemical stain to detect amyloid plaques of Alzheimer's disease (AD) brain sections. An analysis of fluorescence spectra demonstrated that FSB shows approximately twofold fluorescence intensity relative to the conventional styrylbenzene derivative, (EE)-1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy) styrylbenzene (BSB). Moreover, FSB was found to stain amyloid plaques and neurofibrillary tangles of AD brains with greater fluorescence intensity and a lower level of background signals compared to BSB. These finding indicate that FSB can be an excellent fluorescent compound to label human amyloid lesions with high sensitivity and specificity. Because of the possession of a nuclide with a quantized angular momentum, both FSB and [C-13]BSB are also potential contrast agents for magnetic resonance imaging to locate AD pathologies in vivo. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.02.013
• 作为产物：
  描述：

  5-甲酰基-2-甲氧基苯甲酸甲酯 、 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以50%的产率得到methyl 5-[(E)-2-[3-bromo-4-[(E)-2-(4-methoxy-3-methoxycarbonylphenyl)(113C)ethenyl]phenyl](213C)ethenyl]-2-methoxybenzoate
  参考文献：
  名称：

  Fluoro-substituted and 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques

  摘要：

  Two styrylbenzene derivatives, (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB) and (EE)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha,alpha'-C-13(2) ([C-13]BSB), were synthesized for use as a histochemical stain to detect amyloid plaques of Alzheimer's disease (AD) brain sections. An analysis of fluorescence spectra demonstrated that FSB shows approximately twofold fluorescence intensity relative to the conventional styrylbenzene derivative, (EE)-1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy) styrylbenzene (BSB). Moreover, FSB was found to stain amyloid plaques and neurofibrillary tangles of AD brains with greater fluorescence intensity and a lower level of background signals compared to BSB. These finding indicate that FSB can be an excellent fluorescent compound to label human amyloid lesions with high sensitivity and specificity. Because of the possession of a nuclide with a quantized angular momentum, both FSB and [C-13]BSB are also potential contrast agents for magnetic resonance imaging to locate AD pathologies in vivo. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.02.013

文献信息

• Fluoro-substituted and 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques
  作者：Kumi Sato、Makoto Higuchi、Nobuhisa Iwata、Takaomi C Saido、Kazumi Sasamoto

  DOI：10.1016/j.ejmech.2004.02.013

  日期：2004.7

  Two styrylbenzene derivatives, (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB) and (EE)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha,alpha'-C-13(2) ([C-13]BSB), were synthesized for use as a histochemical stain to detect amyloid plaques of Alzheimer's disease (AD) brain sections. An analysis of fluorescence spectra demonstrated that FSB shows approximately twofold fluorescence intensity relative to the conventional styrylbenzene derivative, (EE)-1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy) styrylbenzene (BSB). Moreover, FSB was found to stain amyloid plaques and neurofibrillary tangles of AD brains with greater fluorescence intensity and a lower level of background signals compared to BSB. These finding indicate that FSB can be an excellent fluorescent compound to label human amyloid lesions with high sensitivity and specificity. Because of the possession of a nuclide with a quantized angular momentum, both FSB and [C-13]BSB are also potential contrast agents for magnetic resonance imaging to locate AD pathologies in vivo. (C) 2004 Elsevier SAS. All rights reserved.