(trans,trans)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene | 760988-03-2

• 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: (trans,trans)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene
• 英文别名: (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy-styryl)benzene；(E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxystyryl)benzene；(E,E)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene；(E,E)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxystyryl)benzene；FSB；1-Fluoro-2,5-bis[(E)-3-carboxy-4-hydroxystyryl]benzene；5-[(E)-2-[4-[(E)-2-(3-carboxy-4-hydroxyphenyl)ethenyl]-3-fluorophenyl]ethenyl]-2-hydroxybenzoic acid
• CAS: 760988-03-2
• 化学式: C₂₄H₁₇FO₆
• 分子量: 420.394
• InChiKey: DZXZHGCGNRRJEG-WMWQKROPSA-N

物化性质

• 熔点：
  294 °C (decomp)
• 沸点：
  663.3±55.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)
• 闪点：
  87°C
• 溶解度：
  二甲基亚砜：200mg/mL
• 最大波长(λmax)：
  λ: 360-380 nm Amax: 0.6-0.9

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• WGK Germany：
  1

反应信息

• 作为产物：
  描述：

  [4-(Diethoxy-phosphorylmethyl)-2-fluoro-benzyl]-phosphonic acid diethyl ester 在 氢氧化钾 、 sodium methylate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (trans,trans)-1-fluoro-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene
  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

• An Expedient Synthesis of the Fibril Binding Compound FSB via Sequential Pd-Catalyzed Coupling Reactions
  作者：Mette Louise H. Mantel、Lina S. Søbjerg、Tri H. V. Huynh、Jean-Philippe Ebran、Anders T. Lindhardt (né Hansen)、Niels C. Nielsen、Troels Skrydstrup

  DOI：10.1021/jo7026189

  日期：2008.5.1

  well-known for its binding to β-amyloid peptide fibrils, was synthesized in an efficient manner exploiting two sequential palladium(0)-catalyzed coupling reactions in a 34% overall yield. This is a substantial improvement to the previously reported synthesis of FSB in 1.1%.

  苯乙烯基苯衍生物（E，E）-1-氟-2,5-双（3-羟基羰基-4-羟基）苯乙烯基苯（FSB）以与β-淀粉样肽原纤维的结合而闻名。有效的方式利用两个顺序的钯（0）催化的偶联反应，总产率为34％。这是对先前报道的FSB合成的1.1％的重大改进。
• METHOD OF DETECTING STRUCTURAL CHANGE OF PROTEIN IMMOBILIZED ON SUBSTRATE
  申请人：Fuence Co., Ltd.

  公开号：EP1798555A1

  公开（公告）日：2007-06-20

  This invention provides a method for detection of conformational change of a protein immobilized on a substrate. In concrete, the method comprises, forming a sample film comprising a protein immobilized on a substrate, adding a substance to be detected for its activity to affect to the conformational change of the protein onto the sample film, and detecting the conformational change of the protein. The method enables to measure conformational change of a protein with immobilized state, using minute amount of protein in a short period for a number of samples in a short period all at once, rapidly and simply.

  本发明提供了一种检测固定在基底上的蛋白质构象变化的方法。具体地说，该方法包括：将固定在基底上的蛋白质制成样品膜；在样品膜上加入一种待检测物质，以检测该物质对蛋白质构象变化的影响；检测蛋白质的构象变化。该方法可在短时间内使用微量蛋白质，一次性、快速、简便地测量固定状态下蛋白质的构象变化，并可在短时间内测量多个样品。
• METHOD AND KIT FOR DISCRIMINATING BETWEEN PARKINSON'S DISEASE AND MULTIPLE SYSTEM ATROPHY
  申请人：Osaka University

  公开号：EP3922723A1

  公开（公告）日：2021-12-15

  A method for discriminating between Parkinson's disease and multiple system atrophy, the method comprising the steps of: (1) preparing a solution containing α-synuclein monomers having a tendency to produce rod-like aggregates and/or a solution containing α-synuclein monomers having a tendency to produce twisted aggregates; (2) adding a biological sample from a subject to the solution (s) containing the α-synuclein monomers prepared in step (1); (3) allowing the α-synuclein monomers to aggregate in the solution(s) obtained in step (2); and (4) detecting α-synuclein aggregates formed in step (3).

  一种鉴别帕金森病和多系统萎缩的方法，该方法包括以下步骤(1) 制备含有α-突触核蛋白单体的溶液，α-突触核蛋白单体具有产生杆状聚集体的倾向和/或含有α-突触核蛋白单体的溶液，α-突触核蛋白单体具有产生扭曲聚集体的倾向；(2) 向步骤(1)中制备的含有α-突触核蛋白单体的溶液中加入受试者的生物样本；(3) 使α-突触核蛋白单体在步骤(2)中获得的溶液中聚集；以及 (4) 检测步骤(3)中形成的α-突触核蛋白聚集体。
• Isotope-Labeling of the Fibril Binding Compound FSB via a Pd-Catalyzed Double Alkoxycarbonylation
  作者：Mia N. Burhardt、Rolf Taaning、Niels Chr. Nielsen、Troels Skrydstrup

  DOI：10.1021/jo300746x

  日期：2012.6.15

  We have synthesized two isotopically labeled variants of the beta-amyloid binding compound FSB possessing C-13-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The C-13-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated C-13-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.
• A Versatile Approach to β-Amyloid Fibril-Binding Compounds Exploiting the Shirakawa/Hayashi Protocol for <i>trans</i>-Alkene Synthesis
  作者：Tri H. V. Huynh、Mette Louise H. Mantel、Katrine Mikkelsen、Anders T. Lindhardt、Niels Chr. Nielsen、Daniel Otzen、Troels Skrydstrup

  DOI：10.1021/ol8029593

  日期：2009.2.19

  Application of the Sonogashira coupling reaction followed by a trans-selective alkyne reduction proved highly adaptable for the efficient synthesis of a class of beta-amyloid fibril binding compounds possessing a styrylbenzene motif such as FSB, an FSB dimer, and F-19-BAY94-9172.