N-(2-azidoethyl)-N-methylaniline | 1249429-26-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-azidoethyl)-N-methylaniline
• CAS: 1249429-26-2
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: JAQGZIQSMOIBEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-azidoethyl)-N-methylaniline 在 copper(ll) sulfate pentahydrate 、 铜 、 nitrosonium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  为生物传感应用设计的 3-(杂芳基)-7-羟基香豆素的合成路线

  摘要：

  提出了一种合成 3-(2-苯并咪唑基)-7-羟基香豆素的简单方法，该方法基于 7-乙酰氧基-3-甲酰基香豆素与各种 C-和/或 N-取代的邻苯二胺衍生物的缩合反应。这种不寻常的方法被证明对于将不同的亲水基团（羧酸或磺酸或三甲基烷基铵部分）引入杂芳基支架特别有效，导致发出青绿色的香豆素，在生理条件下既是水溶性的，又是强荧光的。该缩合反应进一步扩展为双（2-氨基苯基）二硒化物，使得首次合成 3-（2-苯并硒唑基）-7-羟基香豆素成为可能。

  DOI：

  10.1002/ejoc.201403215
• 作为产物：
  描述：

  N-methyl-N-{(ω-tosylhydroxy)-1-ethyl}aniline 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以2.5 g的产率得到N-(2-azidoethyl)-N-methylaniline
  参考文献：
  名称：

  通过客体-客体络合来调节水溶性3-羟基黄酮衍生物的发射†

  摘要：

  3-羟基黄酮衍生物作为在水性介质中进行生物标记的荧光探针具有巨大的潜力。他们在各种有机溶剂中对“激发态分子内质子转移”过程进行了广泛研究，但由于水溶性差，因此很少在水溶液中处理。在此，设计并合成了带有3-羟基黄酮和低聚环氧乙烷的两亲分子（表示为3HF-EO）。与有机溶剂中的荧光不同，水溶液中的3HF-EO表现出显着的单一荧光发射，这归因于其阴离子种类的荧光。我们发现荧光强度可以通过主客复合物。α-CD对排放几乎没有影响，而β-CD和γ-CD分别导致3HF-EO的排放增加和减少。的1个H NMR和2D NOESY NMR谱表明，α-CD几乎没有与任何相互作用3HF-EO，而β-CD，γ-CD形成的络合物与一个和两个3HF-EO分别分子。这些结果为调制的荧光强度提供了合理的解释。

  DOI：

  10.1039/c8sm00349a

文献信息

• Fluorogenic/Fluorescent Probes Derivative from Sulfoxanthene, and Use Thereof
  申请人：bioMérieux

  公开号：US20160146814A1

  公开（公告）日：2016-05-26

  The invention relates to fluorescent/fluorogenic probes of formula (I″) or (II″): wherein Z is chosen between: —NH 2 and —OH, or in the fluorescence quencher group consisting of: —NO 2 ; —N═N—R 1 ; R 1 being any organic group that does not obscure the corresponding azo bond; —NHCO-Pept.; Pept. being a peptide residue or any organic group that does not obscure the corresponding amide bond; —O-Glyc.; Glyc. being a oligoglycoside residue that does not obscure the corresponding glycosidic bond; —O—C(O)—R 2 ; —O—P(O)(OR 2 )(OR 2 ′) and —O—S(O) 2 —R 2 ; R 2 and R 2 ′ being independently a hydrogen atom or an organic group that does not obscure the corresponding ester bond; and R a , R b , R c , R d and R e being independently a hydrogen atom or any organic group that does not obscure the corresponding arylether bond so as not to prevent its possible cleavage by a myeloperoxidase activity. It also relates to the use of these fluorescent/fluorogenic probes, for the detection of an enzyme activity, notably in order to identify/discriminate microorganisms in function of their ability to express particular enzyme activities.

  该发明涉及式(I″)或(II″)的荧光/荧光探针： 其中Z在以下选项中选择：—NH2和—OH，或者在荧光猝灭剂基团中选择：—NO2；—N═N—R1；其中R1是任何不遮挡相应偶氮键的有机基团；—NHCO-Pept.；Pept.是肽残基或任何不遮挡相应酰胺键的有机基团；—O-Glyc.；Glyc.是不遮挡相应糖苷键的寡糖苷残基；—O—C(O)—R2；—O—P(O)(OR2)(OR2′)和—O—S(O)2—R2；其中R2和R2′独立地是氢原子或不遮挡相应酯键的有机基团；以及Ra、Rb、Rc、Rd和Re独立地是氢原子或任何不遮挡相应芳基醚键的有机基团，以便不阻止其可能被髓过氧化酶活性水解。 该发明还涉及这些荧光/荧光探针的用途，用于检测酶活性，特别是为了根据微生物表达特定酶活性的能力来识别/区分微生物。
• Bioconjugatable Azo-Based Dark-Quencher Dyes: Synthesis and Application to Protease-Activatable Far-Red Fluorescent Probes
  作者：Arnaud Chevalier、Cédrik Massif、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1002/chem.201203427

  日期：2013.1.28

  We describe the efficient synthesis and one‐step derivatization of novel, nonfluorescent azo dyes based on the Black Hole Quencher‐3 (BHQ‐3) scaffold. These dyes were equipped with various reactive and/or bioconjugatable groups (azido, α‐iodoacetyl, ketone, terminal alkyne, vicinal diol). The azido derivative was found to be highly reactive in the context of copper‐catalyzed azide–alkyne cycloaddition

  我们描述了基于黑洞Quencher-3（BHQ-3）支架的新型非荧光偶氮染料的高效合成和一步衍生。这些染料配备了各种反应性和/或生物结合性基团（叠氮基，α-碘乙酰基，酮，末端炔烃，邻二醇）。发现叠氮衍生物在铜催化的叠氮化物-炔烃环加成（CuAAC）反应中具有很高的反应活性，可以轻松合成第一批水溶性（磺化衍生物）和醛改性的BHQ-3染料，直接常规偶氮偶联反应无法制备。通过形成稳定的肟或硫醚键，可以轻松地将含醛和α-碘乙酰基的荧光猝灭剂与含氨氧基和半胱氨酸的肽偶联。
• The first latent green fluorophores for the detection of azoreductase activity in bacterial cultures
  作者：Arnaud Chevalier、Claire Mercier、Laura Saurel、Sylvain Orenga、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1039/c3cc44798g

  日期：——

  An efficient synthesis of original bio-reductive probes suitable for the detection of azoreductases from the fluorescent rhodamine 110 dye is presented. A “turn-on” green fluorescence response upon reduction of the two diazo bonds of these latent fluorophores was observed both in vitro and in the context of bacterial cultures.

  本文介绍了从荧光罗丹明 110 染料中高效合成适用于检测偶氮还原酶的原始生物还原探针的方法。在体外和细菌培养环境中都观察到了这些潜伏荧光团的两个重氮键被还原后产生的 "开启 "绿色荧光反应。
• Cell-penetrating peptoids: Introduction of novel cationic side chains
  作者：Dominik K. Kölmel、Anna Hörner、Franziska Rönicke、Martin Nieger、Ute Schepers、Stefan Bräse

  DOI：10.1016/j.ejmech.2014.03.078

  日期：2014.5

  During the last decade peptoid-based molecular transporters have been broadly applied. They are highly valued for their easy synthesis and their superior stability against enzymatic degradation. The special structure of peptoids generally allows introducing a variety of different side chains. Yet, the cationic side chains of cell-penetrating peptoids displayed solely lysine- or arginine-like structures. Thus this report is intended to extend the spectrum of cationic peptoid side chains. Herein, we present novel functional groups, like polyamines, aza-crown ethers, or triphenylphosphonium ions that are introduced into peptoids for the first time. In addition, the obtained peptoids were tested for their cell-penetrating properties. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.tetlet.2014.10.053

  日期：2014.12

  Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher (R) (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the 'clickable' azido and thiol-reactive derivatives was notably demonstrated through the preparation of the first water-soluble BHQ-1 dye and a FRET-based probe suitable for the detection of urokinase-type plasminogen activator (uPA), a key protease in cancer invasion and metastasis, respectively. (C) 2014 Elsevier Ltd. All rights reserved.