2-(2-fluorobiphenyl-4-yl)-2-hydroxyacetic acid | 69974-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-fluorobiphenyl-4-yl)-2-hydroxyacetic acid
• 英文别名: 2-(3-fluoro-4-phenylphenyl)-2-hydroxyacetic acid
• CAS: 69974-50-1
• 化学式: C₁₄H₁₁FO₃
• 分子量: 246.238
• InChiKey: CYHXBDHXEYVVHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-fluorobiphenyl-4-yl)-2-hydroxyacetic acid 在 重水 、 4-羟乙基哌嗪乙磺酸 作用下， 反应 48.0h， 生成
  参考文献：
  名称：

  工程化丙二酸丙二酸脱羧酶的混杂消旋酶活性

  摘要：

  支气管败血波氏杆菌中的芳基丙二酸脱羧酶（AMDase）G74C变体对profens具有独特的消旋作用。通过蛋白质工程，基于脱羧反应的活性降低和消旋活性的两倍提高，获得了向混杂消旋化20倍的变体G74C / V43A。该突变体显示出扩大的底物范围，对酮洛芬的反应速率提高了30倍。分子动力学模拟和消旋酶的底物特征表明，底物结构的空间和极性效应在催化方面比单纯的动力学α-质子酸度起着更大的作用。β，γ-不饱和羧酸的转化不会导致重排形成其α，β异构体的观察结果表明，这是一个协调的机制，而不是逐步的机制。有趣的是，

  DOI：

  10.1002/chem.201001924
• 作为产物：
  描述：

  4-溴-3-氟甲苯 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 四丁基溴化铵 、 叔丁基锂 、 palladium diacetate 、 sodium carbonate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 水 为溶剂， 反应 10.06h， 生成 2-(2-fluorobiphenyl-4-yl)-2-hydroxyacetic acid
  参考文献：
  名称：

  Inhibition of Amyloidogenesis by Nonsteroidal Anti-inflammatory Drugs and Their Hybrid Nitrates

  摘要：

  Poor blood-brain barrier penetration of nonsteroidal anti-inflammatory drugs (NSAIDs) has been blamed for the failure of the selective amyloid lowering agent (SALA) R-flurbiprofen in phase 3 clinical trials for Alzheimer's disease (AD). NO-donor NSAIDs (NO-NSAIDs) provide an alternative, gastric-sparing approach to NSAID SALAs, which may improve bioavailability. NSAID analogues were studied for anti-inflammatory activity and for SALA activity in N2a neuronal cells transfected with human amyloid precursor protein (APP). Flurbiprofen (I) analogues were obtained with enhanced anti-inflammatory and antiamyloidogenic properties compared to I, however, esterification led to elevated A beta(1-42) levels. Hybrid nitrate prodrugs possessed superior anti-inflammatory activity and reduced toxicity relative to the parent NSAIDs, including clinical candidate CHF5074. Although hybrid nitrates elevated A beta(1-42) at higher concentration, SALA activity was observed at low concentrations (<= 1 mu M): both A beta(1-42) and the ratio of A beta(1-42)/A beta(1-40) were lowered. This biphasic SALA activity was attributed to the intact nitrate drug. For several compounds, the selective modulation of amyloidogenesis was tested using an immunoprecipitation MALDI-TOF approach. These data support the development of NO-NSAIDs as an alternative approach toward a clinically useful SALA.

  DOI：

  10.1021/jm101450p

文献信息

• Polymer-Supported Ionic-Liquid-Like Phases (SILLPs): Transferring Ionic Liquid Properties to Polymeric Matrices
  作者：Victor Sans、Naima Karbass、M. Isabel Burguete、Vicente Compañ、Eduardo García-Verdugo、Santiago V. Luis、Milena Pawlak

  DOI：10.1002/chem.201001873

  日期：2011.2.7

  The physico‐chemical properties of polymers with ionic‐liquid‐like moieties covalently bound to their surfaces (SILLPs) have been studied by thermal and spectroscopic techniques, as well as by direct impedance and dielectric measurements, and compared to those of the corresponding bulk ionic liquids. The effective transfer of properties from ionic liquids in solution to the supported species has thereby

  已经通过热学和光谱技术以及直接阻抗和介电测量研究了具有共价键合到其表面（SILLPs）的离子液体样部分的聚合物的理化性质，并将其与相应的本体离子相比较。液体。从而证明了性质从溶液中的离子液体到载体物种的有效转移。研究了这些可调“固体溶剂”的化学性质对其宏观溶胀和微波加热的影响，以及固定在SILLPs上的不同催化部分的稳定性和活性。最后，在微波加热中观察到的实验效果可以直接与tanδ的值相关联 δ从介电测量结果导出。
• ——
  作者：MIURA KEHNDZI、 KONDO YASUAKI、 XAN MASATOSI、 MATSUNAGA EHJITI

  DOI：——

  日期：——
• JPS60243040A
  申请人：——

  公开号：JPS60243040A

  公开（公告）日：1985-12-03
• Engineering the Promiscuous Racemase Activity of an Arylmalonate Decarboxylase
  作者：Robert Kourist、Yusuke Miyauchi、Daisuke Uemura、Kenji Miyamoto

  DOI：10.1002/chem.201001924

  日期：2011.1.10

  Variant G74C of arylmalonate decarboxylase (AMDase) from Bordatella bronchoseptica has a unique racemising activity towards profens. By protein engineering, variant G74C/V43A with a 20‐fold shift towards promiscuous racemisation was obtained, based on a reduced activity in the decarboxylation reaction and a two‐fold increase in the racemisation activity. The mutant showed an extended substrate range

  支气管败血波氏杆菌中的芳基丙二酸脱羧酶（AMDase）G74C变体对profens具有独特的消旋作用。通过蛋白质工程，基于脱羧反应的活性降低和消旋活性的两倍提高，获得了向混杂消旋化20倍的变体G74C / V43A。该突变体显示出扩大的底物范围，对酮洛芬的反应速率提高了30倍。分子动力学模拟和消旋酶的底物特征表明，底物结构的空间和极性效应在催化方面比单纯的动力学α-质子酸度起着更大的作用。β，γ-不饱和羧酸的转化不会导致重排形成其α，β异构体的观察结果表明，这是一个协调的机制，而不是逐步的机制。有趣的是，
• Inhibition of Amyloidogenesis by Nonsteroidal Anti-inflammatory Drugs and Their Hybrid Nitrates
  作者：Isaac T. Schiefer、Samer Abdul-Hay、Huali Wang、Michael Vanni、Zhihui Qin、Gregory R. J. Thatcher

  DOI：10.1021/jm101450p

  日期：2011.4.14

  Poor blood-brain barrier penetration of nonsteroidal anti-inflammatory drugs (NSAIDs) has been blamed for the failure of the selective amyloid lowering agent (SALA) R-flurbiprofen in phase 3 clinical trials for Alzheimer's disease (AD). NO-donor NSAIDs (NO-NSAIDs) provide an alternative, gastric-sparing approach to NSAID SALAs, which may improve bioavailability. NSAID analogues were studied for anti-inflammatory activity and for SALA activity in N2a neuronal cells transfected with human amyloid precursor protein (APP). Flurbiprofen (I) analogues were obtained with enhanced anti-inflammatory and antiamyloidogenic properties compared to I, however, esterification led to elevated A beta(1-42) levels. Hybrid nitrate prodrugs possessed superior anti-inflammatory activity and reduced toxicity relative to the parent NSAIDs, including clinical candidate CHF5074. Although hybrid nitrates elevated A beta(1-42) at higher concentration, SALA activity was observed at low concentrations (<= 1 mu M): both A beta(1-42) and the ratio of A beta(1-42)/A beta(1-40) were lowered. This biphasic SALA activity was attributed to the intact nitrate drug. For several compounds, the selective modulation of amyloidogenesis was tested using an immunoprecipitation MALDI-TOF approach. These data support the development of NO-NSAIDs as an alternative approach toward a clinically useful SALA.