4-(2-Fluoroanilino)-4-oxobutanoic acid | 193952-10-2

• 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: 4-(2-Fluoroanilino)-4-oxobutanoic acid
• CAS: 193952-10-2
• 化学式: C₁₀H₁₀FNO₃
• mdl: MFCD00029829
• 分子量: 211.193
• InChiKey: UWBFZPLATNJACG-UHFFFAOYSA-N

物化性质

• 沸点：
  445.6±30.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-Fluoroanilino)-4-oxobutanoic acid 、 三甲基氯化锡 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 trimethylstannic[3-(2-fluorophenylamido)propanoate]
  参考文献：
  名称：

  Design, synthesis, and Gaussia luciferase Assay of triorganotin(IV)-based HCV inhibitors

  摘要：

  The discovery and optimization of a novel triorganotin(IV) complexes with anti-HCV properties are presented. Organotin(IV) moiety has the ability to bind phosphate group of RNA backbone. The organotin(IV) moiety is bonded with ligands and groups, which are known for inhibiting HCV enzymes. Triorganotin(IV) complexes were synthesized and evaluated for their potency against HCV by using luciferase assay. Structure-activity relationship studies led to the identification of Tributyltannic[3-(3',4'-dichlorophenylamido)propanoate] (compound 1) as a potent HCV inhibitor, with log IC50 values 0.79 nM in the cell-based assay. Triorganotin(IV) complexes containing chlorine and nitro group display higher potency. Gaussia luciferase Assay shows that among triorganotin(IV) derivatives, butyl substituted triorganotin(IV) complexes are more active than methyl- and phenyl-substituted complexes.HCV infection can lead to hepatocellular carcinoma, and is a major reason for liver transplantation. The worldwide prevalence of chronic HCV infection is estimated to be approaching 270-300 million people, but patients and physicians are still waiting for effective anti-HCV drugs. With this background, organotin(IV) complexes are synthesized and screened against HCV using Gaussia luciferase assay. Organotin(IV) complexes are selected due to their ability to interact with both DNA constituents and enzymes.

  DOI：

  10.1007/s00044-014-1242-3
• 作为产物：
  描述：

  丁二酸酐 、 2-氟苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-(2-Fluoroanilino)-4-oxobutanoic acid
  参考文献：
  名称：

  通过靶向 PI3K/Akt/mTOR 信号通路作为抗肿瘤剂的苯胺（二羧酸）紫草素酯的设计、合成和生物学评价

  摘要：

  三阴性乳腺癌（TNBC）因其分化低、增殖快和远处转移率高而预后不良。PI3K/Akt/mTOR 作为细胞内信号通路在细胞增殖、迁移、侵袭、代谢和再生中起关键作用。在这项工作中，我们设计并合成了一系列针对 PI3K/Akt/mTOR 信号通路的苯胺（二羧酸）紫草素酯，并评估了它们的抗肿瘤作用。通过计算机辅助药物设计方法（CADD）的三轮筛选，我们初步获得了十六种新型苯胺（二羧酸）紫草素酯，并鉴定为优良化合物。CCK-8 测定结果表明化合物 M9 对 MDA-MB-231、A549 和 HeLa 细胞系表现出比紫草素（SK）更好的抗增殖活性，50 = 4.52 ± 0.28 μM；SK：IC 50= 7.62 ± 0.26 μM）。此外，M9的抗增殖活性优于紫杉醇。进一步的药理研究表明，M9 可以诱导 MDA-MB-231 细胞凋亡并在 G2/M 期阻滞细胞周期。M9 还通过抑制 Wnt/β-catenin

  DOI：

  10.1016/j.bioorg.2021.104872

文献信息

• <i>N</i> ‐Aryl Amides as Chemical Exchange Saturation Transfer Magnetic Resonance Imaging Contrast Agents
  作者：Xuekang Cai、Jia Zhang、Jiaqi Lu、Long Yi、Zheng Han、Shuixing Zhang、Xing Yang、Guanshu Liu

  DOI：10.1002/chem.202002415

  日期：2020.9.10

  amides. As the first proof‐of‐concept study, we used CEST MRI to detect the enzymatic metabolism of the drug acebutolol directly by its intrinsic CEST signal without any chemical labeling. Our study implies that N‐aryl amides may enable the label‐free CEST MRI detection of the metabolism of many N‐aryl amide‐containing drugs and a variety of enzymes that act on N‐aryl amides, greatly expanding the scope

  化学交换饱和转移 (CEST) MRI 最近已成为一种通用的分子成像方法，其中可以利用抗磁性化合物生成 MRI 信号。为了扩大 CEST MRI 的应用范围，我们在此系统地研究了具有不同N芳族取代基的N芳基酰胺的 CEST 特性，揭示了它们的化学位移 (4.6–5.8 ppm) 和交换率（高达数千 s -1）与烷基酰胺相比，更适合用作 CEST 试剂。作为第一个概念验证研究，我们使用 CEST MRI 直接通过其固有的 CEST 信号检测药物醋丁洛尔的酶代谢，无需任何化学标记。我们的研究表明N芳基酰胺可能使许多含N-芳基酰胺的药物和作用于N-芳基酰胺的多种酶的代谢的无标记CEST MRI检测成为可能，极大地扩展了CEST MR分子成像的范围。
• Methods and compositions for determining the sequence of nucleic acid molecules
  申请人：QIAGEN Genomics, Inc.

  公开号：US20040115694A1

  公开（公告）日：2004-06-17

  Methods and compounds, including compositions therefrom, are provided for determining the sequence of nucleic acid molecules. The methods permit the determination of multiple nucleic acid sequences simultaneously. The compounds are used as tags to generate tagged nucleic acid fragments which are complementary to a selected target nucleic acid molecule. Each tag is correlative with a particular nucleotide and, in a preferred embodiment, is detectable by mass spectrometry. Following separation of the tagged fragments by sequential length, the tags are cleaved from the tagged fragments. In a preferred embodiment, the tags are detected by mass spectrometry and the sequence of the nucleic acid molecule is determined therefrom. The individual steps of the methods can be used in automated format, e.g., by the incorporation into systems.

  提供了用于确定核酸分子序列的方法和化合物，包括从中制备的组合物。该方法允许同时确定多个核酸序列。这些化合物被用作标记，以生成与所选目标核酸分子互补的带标记的核酸片段。每个标记与特定的核苷酸相关，在优选实施例中，可以通过质谱法检测到。在通过顺序长度分离带标记的片段后，将从带标记的片段中切除标记。在优选实施例中，通过质谱法检测标记，并从中确定核酸分子的序列。该方法的各个步骤可以以自动化格式使用，例如通过纳入系统中。
• METHODS AND COMPOSITIONS FOR ANALYZING NUCLEIC ACID MOLECULES UTILIZING SIZING TECHNIQUES
  申请人：Van Ness Jeffrey

  公开号：US20060057566A1

  公开（公告）日：2006-03-16

  Tags and linkers specifically designed for a wide variety of nucleic acid reactions are disclosed, which are suitable for a wide variety of nucleic acid reactions wherein separation of nucleic acid molecules based upon size is required.

  本发明揭示了专门设计用于各种核酸反应的标签和连接剂，适用于需要基于大小分离核酸分子的各种核酸反应。
• Methods and compositions for detecting binding of ligand pair using non-fluorescent label
  申请人：Rapigene, Inc.

  公开号：EP0962464A2

  公开（公告）日：1999-12-08

  Methods are provided for detecting the binding of a first member to a second member of a ligand pair, comprising the steps of (a) combining a set of first tagged members with a biological sample which may contain one or more second members, under conditions, and for a time sufficient to permit binding of a first member to a second member, wherein said tag is correlative with a particular first member and detectable by non-fluorescent spectrometry, or potentiometry; (b) separating bound first and second members from unbound members; (c) cleaving the tag from the tagged first member; and (d) detecting the tag by non-fluorescent spectrometry, or potentiometry, and therefrom detecting the binding of the first member to the second member.

  本发明提供了检测配体对中第一成员与第二成员结合的方法，包括以下步骤：(a) 在足以允许第一成员与第二成员结合的条件和时间下，将一组第一标记成员与可能含有一个或多个第二成员的生物样品结合，其中所述标记与特定的第一成员相关，并可通过非荧光光谱法或电位计法检测；(b) 将结合的第一和第二成员与未结合的成员分离； (c) 从标记的第一成员上裂解标记；以及 (d) 通过非荧光光谱法或电位测定法检测标记，并由此检测第一成员与第二成员的结合情况。
• Methods and compositions for enhancing sensitivity in the analysis of biological-based assays
  申请人：QIAGEN Genomics, Inc.

  公开号：US20030077595A1

  公开（公告）日：2003-04-24

  Methods are provided for detecting the binding of a first member to a second member of a ligand pair, comprising the steps of (a) combining a set of first tagged members with a biological sample which may contain one or more second members, under conditions, and for a time sufficient to permit binding of a first member to a second member, wherein said tag is correlative with a particular first member and detectable by non-fluorescent spectrometry, or potentiometry, (b) separating bound first and second members from unbound members, (c) cleaving the tag from the tagged first member, and (d) detecting the tag by non-fluorescent spectrometry, or potentiometry, and therefrom detecting the binding of the first member to the second member .

  本发明提供了检测配体对中第一成员与第二成员结合的方法，包括以下步骤：(a) 在足以允许第一成员与第二成员结合的条件和时间下，将一组第一标记成员与可能含有一个或多个第二成员的生物样品结合、其中所述标记与特定的第一成员相关，并可通过非荧光光谱法或电位计法检测；(b) 将结合的第一和第二成员与未结合的成员分离；(c) 从标记的第一成员上裂解标记；(d) 通过非荧光光谱法或电位计法检测标记，并由此检测第一成员与第二成员的结合情况。