(E)-3-(2-fluoro-4-hydroxyphenyl)acrylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2-fluoro-4-hydroxyphenyl)acrylic acid
• 英文别名: 2-fluoro-4-hydroxycinnamic acid；(E)-3-(2-fluoro-4-hydroxyphenyl)prop-2-enoic acid
• 化学式: C₉H₇FO₃
• 分子量: 182.151
• InChiKey: FYJKSAQOWJFNMW-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-3-(2-fluoro-4-hydroxyphenyl)acrylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到3-(2-fluoro-4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of GPR40/FFAR1 agonists containing 3,5-dimethylisoxazole

  摘要：

  GPR40 is an attractive target due to its glucose-stimulated insulin secretion effect with low risk of causing hypoglycemia, which also can be seen from the clinical studies using TAK-875 (fasiglifam). In the present studies, we discovered a series of analogues containing 3,5-dimethylisoxazole as potent GPR40 agonists, especially compound ilk with an EC50 value of 15.9 nM. Moreover, compound 11k reduced glucose excursion to 23.1% in ICR mice and 29.5% in type 2 diabetic C57BL/6 mice at 30 mg/kg. It also exhibited satisfactory PK profile. Docking studies were conducted to explain the interaction mode of this series. In summary, compound 11k with robust efficacy in vitro and in vivo is a promising drug candidate for further investigation. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.054
• 作为产物：
  描述：

  3-(2-氟苯基)丙-2-烯酸 在 氧气 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 various solvent(s) 为溶剂， 生成 (E)-3-(2-fluoro-4-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  Non-natural cinnamic acid derivatives as substrates of cinnamate 4-hydroxylase

  摘要：

  Cinnamate 4-hydroxylase (C4H), a monooxygenase in the plant phenylpropanoid pathway, was assayed for its ability to hydroxylate 29 substrate analogues. Nine of the tested analogues with various aromatic side chains, including 3-coumaric acid, were metabolized by C4H. Seven products from these reactive analogues were characterized using LC/MS, H-1 NMR and C-13 NMR spectroscopic analysis. For example, caffeic acid was the product of 3-coumaric acid. The products 4-hydroxy-2-chlorocinnamic acid and 4-hydroxy-2-ethoxy-cinnamic acid are novel compounds that have not been previously reported. The kinetic parameters of C4H towards these analogues were determined. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2006.10.018

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Vinylation of Unprotected Phenols Using a Biocatalytic System
  作者：Eduardo Busto、Robert C. Simon、Wolfgang Kroutil

  DOI：10.1002/anie.201505696

  日期：2015.9.7

  conditions to afford the corresponding para‐vinylphenol derivatives while releasing only one molecule of CO2 and water as the by‐products. This transformation was achieved by designing a biocatalytic system that combines three biocatalytic steps, namely the CC coupling of phenol and pyruvate in the presence of ammonia, which leads to the corresponding tyrosine derivative, followed by deamination and decarboxylation

  在大气条件下，将易于获得的取代酚与丙酮酸盐在缓冲溶液中偶联，以提供相应的对乙烯基苯酚衍生物，同时仅释放一分子的CO 2和水作为副产物。这种转化是通过设计一种生物催化系统来实现的，该系统结合了三个生物催化步骤，即在氨气存在下苯酚和丙酮酸的CC偶联，生成相应的酪氨酸衍生物，然后进行脱氨和脱羧。生物催化转化以高区域选择性进行，仅提供所需的对位产品。因此，该方法代表了一种环境友好的方法，可直接以制备规模（0.5 mmol）直接将2-，3-或2,3-二取代的苯酚乙烯基化，从而以高收率（65-83％）提供乙烯基苯酚。
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• Isoxazoline compounds having MIF antagonist activity
  申请人：——

  公开号：US20030008908A1

  公开（公告）日：2003-01-09

  Methods of use and pharmaceutical compositions for a genus of low molecular weight compounds comprising optionally substituted isoxazoline ring systems that act as inhibitors of MIF (macrophage migration inhibitory factor) are disclosed. Specifically, the compounds are useful for treating a variety of diseases involving inflammatory activity or pro-inflammatory cytokine responses, such as autoimmune diseases (including rheumatiod arthritis, insulin-dependent diabetes, multiple sclerosis, graft versus host disease, lupus syndromes), asthma, arthritis, ARDS, psoriasis, interleukin-2 toxicity, proliferative vascular disease, and various forms of sepsis and septic shock, and other conditions characterized by underlying MIF responses including, for instance, tumor growth and neovascularization (angiogenesis).

  本发明公开了一种低分子量化合物的使用方法和药物组合物，该化合物包含可选取代的异噁唑啉环系统，可作为 MIF（巨噬细胞迁移抑制因子）的抑制剂。具体来说，这些化合物可用于治疗多种涉及炎症活动或促炎细胞因子反应的疾病，如自身免疫性疾病（包括风湿性关节炎、胰岛素依赖型糖尿病、多发性硬化症、移植物抗宿主病、狼疮综合征）、慢性肾脏病、糖尿病、高血压、高血脂、高血糖等、狼疮综合征）、哮喘、关节炎、ARDS、银屑病、白细胞介素-2毒性、增生性血管疾病、各种形式的败血症和脓毒性休克，以及其他以潜在的 MIF 反应为特征的疾病，包括肿瘤生长和血管新生（血管生成）等。
• Compounds, compositions, processes of making, and methods of use related to inhibiting macrophage migration inhibitory factor
  申请人：Sielecki-Dzurdz Thais

  公开号：US20050250826A1

  公开（公告）日：2005-11-10

  The present invention provides a compound having Formula I or II: wherein B, R, X, Ar, and Y are defined herein, pharmaceutically acceptable salts thereof and pharmaceutically acceptable prodrugs thereof. The present invention also provides methods of making and using the compound.

  本发明提供了具有式 I 或式 II 的化合物： 其中 B、R、X、Ar 和 Y 在此定义的化合物、其药学上可接受的盐及其药学上可接受的原药。本发明还提供了制造和使用该化合物的方法。