1-{3-[methyl(phenyl)amino]propyl}-2,5-dihydro-1H-pyrrole-2,5-dione | 146426-00-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-{3-[methyl(phenyl)amino]propyl}-2,5-dihydro-1H-pyrrole-2,5-dione
• 英文别名: 1-[3-(N-methylanilino)propyl]pyrrole-2,5-dione
• CAS: 146426-00-8
• 化学式: C₁₄H₁₆N₂O₂
• mdl: MFCD11524387
• 分子量: 244.293
• InChiKey: DBJCHYFZMPMUGF-UHFFFAOYSA-N

物化性质

• 沸点：
  403.0±28.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-甲氧基-5-甲基-4-[(4-甲基-2-硝基苯基)偶氮]苯重氮(T-4)四氯锌酸盐(2:1) 、 1-{3-[methyl(phenyl)amino]propyl}-2,5-dihydro-1H-pyrrole-2,5-dione 以 乙腈 为溶剂， 反应 2.0h， 以59%的产率得到1-[3-[4-[[2-methoxy-5-methyl-4-[(4-methyl-2-nitrophenyl)diazenyl]phenyl]diazenyl]-N-methylanilino]propyl]pyrrole-2,5-dione
  参考文献：
  名称：

  Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.10.053
• 作为产物：
  描述：

  马来酸酐 、 N-(3-氨丙基)-N-甲基苯胺 在 ice 、 乙酸酐 、 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 ethyl acetate n-hexane 作用下， 以 二氯甲烷 为溶剂， 反应 53.0h， 生成 1-{3-[methyl(phenyl)amino]propyl}-2,5-dihydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Phenothiazine derivatives, their production and use

  摘要：

  本发明揭示了一种新的苯并噻嗪衍生物，其一般式为(I)：## STR1 ## 其中R.sub.1，R.sub.2，R.sub.3和R.sub.4相同或不同，为C.sub.1-6烷基，并且其中至少一个具有可与氨基，硫醇基或羧基反应的基团，X.sup.-是苯并噻嗪阳离子的计数离子。本发明还揭示了它们的制备以及在制备过程中使用的中间体。化合物(I)是亚甲蓝的衍生物，适用于癌症光动力疗法或利用化学发光的免疫测定。

  公开号：

  US05532171A1

文献信息

• A Synthetic Route to 3-(Heteroaryl)-7-hydroxycoumarins Designed for Biosensing Applications
  作者：Benoît Roubinet、Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1002/ejoc.201403215

  日期：2015.1

  heteroaryl scaffold, leading to cyan-green emitting coumarins that were both water-soluble and strongly fluorescent under physiological conditions. The further extension of this condensation reaction to bis(2-aminophenyl)diselenide enabled the first synthesis of 3-(2-benzoselenazolyl)-7-hydroxycoumarin. The potential utility of these new 7-hydroxycoumarins was demonstrated through the synthesis and spectroscopic

  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。
• Azo-Sulforhodamine Dyes: A Novel Class of Broad Spectrum Dark Quenchers
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol501753b

  日期：2014.8.1

  A rapid access to a novel class of water-soluble dark quencher dyes was achieved using an azo-coupling reaction between a fluorescent primary arylamine derived from a sulforhodamine 101 scaffold and a tertiary aniline equipped with different bioconjugatable groups. The thus obtained nonfluorescent azo-sulforhodamine hybrids display a broad quenching range spanning the visible to NIR regions. This was demonstrated through the preparation and enzymatic activation of FRET-based fluorogenic substrates of urokinase.
• Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.tetlet.2014.10.054

  日期：2014.12

  A further extension of the efficient synthetic methodology described in Part I, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry (R) Quencher 650 (BBQ-650 (R)) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-type plasminogen activator. (C) 2014 Elsevier Ltd. All rights reserved.
• US5344928A
  申请人：——

  公开号：US5344928A

  公开（公告）日：1994-09-06
• US5532171A
  申请人：——

  公开号：US5532171A

  公开（公告）日：1996-07-02