3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline | 130973-96-5

• 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: 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline
• 英文别名: 3-[3-(trifluoromethyl)diazirin-3-yl]aniline
• CAS: 130973-96-5
• 化学式: C₈H₆F₃N₃
• 分子量: 201.151
• InChiKey: OFNZVAOBGWMWBY-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  264.3±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline 在 sodium methylate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.08h， 生成 6-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
  参考文献：
  名称：

  Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides: biological activities of modified surfaces

  摘要：

  The potential of surface glycoengineering for biomaterials and biosensors originates from the importance of carbohydrate-protein interactions in biological systems. The strategy employed here utilises carbene generated by illumination of diazirine to achieve covalent bonding of carbohydrates. Here, we describe the synthesis of an aryl diazirine containing a disaccharide (lactose). Surface analysis techniques [X-ray photoelectron spectroscopy (XPS) and time of flight secondary ion mass spectroscopy (ToF-SIMS)] demonstrate its successful surface immobilisation on polystyrene (PS). Results are compared to those previously obtained with an aryl diazirine containing a monosaccharide (galactose). The biological activity of galactose- or lactose-modified PS samples is studied using rat hepatocytes, Allo A lectin and solid-phase semi-synthesis with alpha -2,6-sialyltransferase. Allo A shows some binding to galactose-modified PS but none to lactose-modified surfaces. Similar results are obtained with rat hepatocytes. In contrast, sialylation of lactose-modified PS is achieved but not with galactose-modified surfaces. The different responses indicate that the biological activity depends not only on the carbohydrate per se but also on the structure and length of the spacer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00172-9
• 作为产物：
  描述：

  3-(3-nitrophenyl)-3-(trifluoromethyl)-3H-diazirine 在 sodium dithionite 作用下， 以 四氢呋喃 、 重水 为溶剂， 反应 16.0h， 以56%的产率得到3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline
  参考文献：
  名称：

  NLRP3抑制剂重氮嗪光亲和探针的设计，合成和评估

  摘要：

  NLRP3抑制剂MCC950 / CRID3可改善动物模型中的大量炎症性疾病。在本文中，我们描述了一种称为TPD-950-Br的三氟甲基苯基重氮（TPD）光亲和探针，以探测MCC950的分子相互作用。我们显示，TPD-950-Br在NLRP3抑制剂检测中共激活并在光活化后捕获近端物质，并抑制IL-1β的产生。

  DOI：

  10.1016/j.tetlet.2020.151849

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• Process for the modification of surface
  申请人：Centre Suisse d'Electronique et de Microtechnique S.A.

  公开号：US06780980B1

  公开（公告）日：2004-08-24

  The present invention relates to a process for the modification of a material surface comprising the steps of (a1) photochemically fixing one or more different compounds of formula onto the material surface, or (a2) photochemically fixing a compound of formula onto the material surface and subsequently converting the —ZH groups to —Z—X moieties, wherein the variables each have the meanings as given in the claims; and (b) enzymatically attaching one or more further carbohydrates to the X radicals of the modified surface obtained according to stop (a1) or (a2). The materials obtainable by the process of the invention are useful, for example, for the manufacture of biomedical devices including biosensors.

  本发明涉及一种用于修改材料表面的过程，包括以下步骤：(a1) 光化学地将一个或多个不同的化合物按照公式固定在材料表面上，或者(a2) 光化学地将一个按照公式的化合物固定在材料表面上，然后将—ZH基团转化为—Z—X基团，其中变量的含义如索赔中所述；以及(b) 酶促地将一个或多个进一步的碳水化合物连接到根据步骤(a1)或(a2)获得的修改表面的X基团上。根据本发明的工艺获得的材料可用于制造生物医学设备，包括生物传感器。
• An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline: A key intermediate in the synthesis of photoaffinity probes
  作者：Torbjörn Wixe、Fredrik Almqvist

  DOI：10.1016/j.tetlet.2017.07.031

  日期：2017.8

  An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline, achieving an overall yield of 38% over seven steps is reported. Only three chromatographic separations were needed and the preparation of ∼0.7 g of the target compound was demonstrated. The stability of the diazirine in solution at room temperature while exposed to ambient light was studied. No significant degradation of

  据报道，改进了3- [3-（三氟甲基）-3 H -1,2-二叠氮基-3-基]苯胺的合成，在七个步骤中总产率达到了38％。只需要进行三步色谱分离，就可以制备出约0.7 g的目标化合物。研究了重氮嗪在室温下暴露于环境光下在溶液中的稳定性。1 H和19 F NMR证实，在130 mM的样品中，在5周的过程中未观察到化合物的明显降解，而在较弱的样品（10、5和2.5 mM）中仅观察到了较小的降解。
• Photoactive bioadhesive compositions
  申请人：Nanyang Technological University

  公开号：US10005936B2

  公开（公告）日：2018-06-26

  A novel diazirine-based biocompatible polymer that can be used as on-demand or tunable bioadhesive and applied across various clinically important surfaces. The biocompatible polymer comprises a single strand of repeating units and up to 5,000 photoreactive diazirine groups covalently attached to it. A bioadhesive composition comprises the polymer of the present invention and suitable solvents, surfactants, stabilizers, fillers and other additives. The composition may additionally contain metallic particles of size less than 50 micron made of rare earth elements and has UV or NIR transparency less than 1 optical density unit per 1 centimeter. The poly-diazirine surface grafted thin films can be used for minimally invasive surgeries.

  一种新型重氮基生物相容性聚合物，可用作按需或可调生物粘合剂，应用于各种重要的临床表面。这种生物相容性聚合物由单股重复单元和多达 5,000 个共价连接的光活性重氮氨酸基团组成。生物粘合剂组合物由本发明的聚合物和合适的溶剂、表面活性剂、稳定剂、填料和其他添加剂组成。此外，该组合物还可能含有由稀土元素制成的尺寸小于 50 微米的金属颗粒，其紫外线或近红外透明度小于每 1 厘米 1 个光密度单位。聚二氮杂环胺表面接枝薄膜可用于微创手术。
• Substituted bridged urea analogs as sirtuin modulators
  申请人：GLAXOSMITHKLINE LLC

  公开号：US10590135B2

  公开（公告）日：2020-03-17

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥基脲化合物、相应的相关类似物、药物组合物及其使用方法。本发明的Sirtuin调节化合物可用于增加细胞的寿命，治疗和/或预防多种疾病和失调，这些疾病和失调包括但不限于例如与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、凝血障碍、炎症、癌症和/或潮红有关的疾病或失调，以及将受益于线粒体活性增加的疾病或失调。本发明还涉及由sirtuin调节化合物与另一种治疗剂组合而成的组合物。