2-nitro-4-((trimethylsilyl)ethynyl)aniline | 518982-26-8

• 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-nitro-4-((trimethylsilyl)ethynyl)aniline
• 英文别名: 2-nitro-4-(2-trimethylsilylethynyl)aniline
• CAS: 518982-26-8
• 化学式: C₁₁H₁₄N₂O₂Si
• 分子量: 234.33
• InChiKey: HQMMOSQFCNKPFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  323.7±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-4-((trimethylsilyl)ethynyl)aniline 在 甲醇 、 sodium azide 、 palladium on activated charcoal 、 sodium formate 、 potassium carbonate 、 原甲酸三乙酯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 56.0h， 生成 5-(1-(4-methoxyphenethyl)-1H-1,2,3-triazol-4-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Structure–Activity Relationships of Benzimidazole-Based Glutaminyl Cyclase Inhibitors Featuring a Heteroaryl Scaffold

  摘要：

  Glutaminyl cyclase (hQC) has emerged as a new potential target for the treatment of Alzheimer's disease (AD). The inhibition of hQC prevents of the formation of the A beta(3(pE)-40,42) species which were shown to be of elevated neurotoidcity and are likely to act as a seeding core, leading to an accelerated formation of A beta-oligomers and fibrils. This work presents a new class of inhibitors of hQC, resulting from a pharmacophore-based screen. Hit molecules were identified, containing benzimidazole as the metal binding group connected to 1,3,4-oxadiazole as the central scaffold. The subsequent optimization resulted in benzimidazoly1-1,3,4-thiadiazoles and -1,2,3-triazoles with an inhibitory potency in the nanomolar range. Further investigation into the potential binding mode of the new compound classes combined molecular docking and site directed mutagenesis studies.

  DOI：

  10.1021/jm4001709
• 作为产物：
  描述：

  4'-溴乙酰苯胺 在 N,N-二异丙基乙胺 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硝酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 2-nitro-4-((trimethylsilyl)ethynyl)aniline
  参考文献：
  名称：

  Synthesis of nitrile-terminated potential molecular electronic devices

  摘要：

  Several potential molecular devices have been synthesized consisting of oligo(phenylene ethynylene) (OPE) backbones containing a terminal nitrile group alligator clip as a means of attachment to a metal surface. The synthesis of four new nitrile-containing OPEs is discussed, including an improved synthesis of an intermediate used in our prior production of OPEs containing acetate-protected thiol alligator clips. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01527-2

文献信息

• New Class of Bioluminogenic Probe Based on Bioluminescent Enzyme-Induced Electron Transfer: BioLeT
  作者：Hideo Takakura、Ryosuke Kojima、Mako Kamiya、Eiji Kobayashi、Toru Komatsu、Tasuku Ueno、Takuya Terai、Kenjiro Hanaoka、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja511014w

  日期：2015.4.1

  available for functional bioluminescent substrates. We propose a new design strategy (designated as bioluminescent enzyme-induced electron transfer: BioLeT) for luciferin-based bioluminescence probes. Luminescence measurements of a series of aminoluciferin derivatives confirmed that bioluminescence can be controlled by means of BioLeT. Based on this concept, we developed bioluminescence probes for nitric

  生物发光成像 (BLI) 在研究活体动物深层组织中的生物现象方面具有优势，但很少有设计策略可用于功能性生物发光底物。我们为基于荧光素的生物发光探针提出了一种新的设计策略（称为生物发光酶诱导电子转移：BioLeT）。一系列氨基荧光素衍生物的发光测量证实生物发光可以通过 BioLeT 来控制。基于这个概念，我们开发了用于一氧化氮的生物发光探针，即使在体内也能进行定量和灵敏的检测。我们的设计策略应该适用于开发各种实用的生物发光探针。
• [EN] PROTEIN KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINES KINASES
  申请人：ORION CORP

  公开号：WO2014162039A1

  公开（公告）日：2014-10-09

  A compound of formula (I), wherein R1 to R5, A, B, Z, Z1 and Z2 are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.

  公式（I）的化合物，其中R1至R5，A，B，Z，Z1和Z2如权利要求中所定义，并公开其药学上可接受的盐。公式（I）的化合物具有作为FGFR抑制剂的效用，并在需要FGFR激酶抑制的情况下，如癌症治疗中是有用的。
• Effect of head group size on the photoswitching applications of azobenzene Disperse Red 1 analogues
  作者：Alexis Goulet-Hanssens、T. Christopher Corkery、Arri Priimagi、Christopher J. Barrett

  DOI：10.1039/c4tc00996g

  日期：——

  We investigate the effect of the increased molecular bulk in the ‘head’ group for a class of newly synthesized azobenzene chromophores and demonstrate that motifs with larger free-volume changes during isomerization drive photoinduced macromolecular phenomena.

  我们研究了一类新合成的偶氮苯染料分子“头部”基团分子量增加的影响，并证明了在异构化过程中具有更大自由体积变化的结构单元能驱动光诱导大分子现象。
• Bridging Ligand Length Controls AT Selectivity and Enantioselectivity of Binuclear Ruthenium Threading Intercalators
  作者：Johan R. Johansson、Yubo Wang、Mattias P. Eng、Nina Kann、Per Lincoln、Johanna Andersson

  DOI：10.1002/chem.201300483

  日期：2013.5.10

  studied ruthenium complexes, we further conclude that elongation of the bridging ligand reduces the sensitivity of the threading interaction to DNA flexibility, resulting in a decreased AT selectivity for the new complex. We also find that the length of the bridging ligand affects the enantioselectivity with increasing preference for the ΔΔ enantiomer as the bridging ligand becomes longer.

  DNA穿刺嵌入剂的缓慢解离使它们成为寻找新的DNA靶向药物的模型化合物而引起人们的兴趣，因为缓慢解离与生物学活性之间似乎存在关联。因此，了解控制穿线嵌入的机制将具有极大的价值，为此，我们研究了双核钌穿线嵌入剂的桥联配体的长度如何影响其DNA结合特性。我们已经合成了一种新的双核钌穿线嵌入剂，该嵌入剂与ct-DNA的解离动力学相比，对于任何类型的DNA的任何钌配合物来说都比以前观察到的慢，这归因于新配合物的钌中心之间距离的增加。与以前研究过的钌配合物相比，我们进一步得出结论，桥联配体的延伸降低了穿线相互作用对DNA柔韧性的敏感性，从而导致对新复合物的AT选择性降低。我们还发现，随着桥联配体的变长，桥联配体的长度会影响对映选择性，并且对ΔΔ对映体的偏好会增加。
• PHOSPHORESCENT TRANSITION METAL COMPLEX, ITS PREPARATION AND USE
  申请人：City University of Hong Kong

  公开号：US20170114275A1

  公开（公告）日：2017-04-27

  A phosphorescent transition metal complex especially suitable as sensor for hydrogen peroxide in cells, in particular in mitochondria in live cells, includes a metallic central atom, which is a transition metal, a first ligand with at least one pyridine ring, and a second ligand having at least one pyridine ring and at least one structural component selected from the group of 1,2-diketone moiety and an arylboronate moiety. A method for preparing the metal complex is also disclosed as well as a method of detecting hydrogen peroxide in cells by incubating cells with the transition metal complex. The metal complex shows advantageous intense and long-lived phosphorescence accompanied by exceptional cellular localization properties. The metal complex is highly photostable and highly selective towards hydrogen peroxide, thus, especially suitable for detecting mitochondrial H 2 O 2 .

  一种磷光过渡金属配合物，特别适用于细胞中的过氧化氢传感器，特别是在活细胞中的线粒体中，包括一个金属中心原子，该原子是过渡金属，第一配体具有至少一个吡啶环，第二配体具有至少一个吡啶环和从1,2-二酮基团和芳基硼酸酯基团组中选择的至少一个结构组分。还公开了一种制备金属配合物的方法以及通过将细胞与过渡金属配合物孵育来检测细胞中的过氧化氢的方法。该金属配合物显示出优越的强烈和长寿命的磷光，并具有异常的细胞定位特性。该金属配合物具有高光稳定性和高选择性，因此特别适用于检测线粒体H2O2。