ethyl 7-dimethylaminocoumarin-4-acetate | 289699-61-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ethyl 7-dimethylaminocoumarin-4-acetate
• 英文别名: Ethyl 2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetate；ethyl 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate
• CAS: 289699-61-2
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: MHPQHBUJWFAHNU-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  ethyl 7-dimethylaminocoumarin-4-acetate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-[(3-benzoxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]-2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetamide
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s
• 作为产物：
  描述：

  1,3-丙酮二羧酸二乙酯 、 3-羟基-N,N-二甲基苯胺 在 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以63%的产率得到ethyl 7-dimethylaminocoumarin-4-acetate
  参考文献：
  名称：

  Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides

  摘要：

  细胞对蛋白质或抗体运动的追踪、检测和感知是增进我们对生物分子相互作用和活性理解的重要方面。用荧光染料修饰的抗体也是有价值的工具，特别是在免疫学研究中。这里我们描述了一项原理验证研究，涉及一种新的水溶性香豆素探针，该探针具有马来酰亚胺巯基反应单元，用于荧光标记生物分子。重点包括：（1）N-取代马来酰亚胺的便捷水基制备，（2）活化马来酰亚胺酯的一锅法制备，以及（3）硒醇促进的本征二硫键还原和无显著活性损失的抗体“位点特异性”标记的生物偶联方案。

  DOI：

  10.1039/b904060a

文献信息

• Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides
  作者：Hong Y. Song、Mun H. Ngai、Zhen Y. Song、Paul A. MacAry、Jonathan Hobley、Martin J. Lear

  DOI：10.1039/b904060a

  日期：——

  The cellular tracking, detection and sensing of protein or antibody movement are important aspects to advance our understanding of biomolecular interactions and activity. Antibodies modified with fluorescent dyes are also valuable tools, especially in immunology research. We describe here a proof-of-principle study of a new water-soluble coumarin probe with a maleimide thiol-reacting unit to fluorescently tag biomolecules. Highlights include: (1) a convenient water-based preparation of N-substituted maleimides, (2) a one-pot preparation of activated maleimido-esters, and (3) a bio-conjugation protocol for the selenol-promoted reduction of native disulfide bonds and the ‘site-specific’ labelling of antibodies with no significant loss of activity.

  细胞对蛋白质或抗体运动的追踪、检测和感知是增进我们对生物分子相互作用和活性理解的重要方面。用荧光染料修饰的抗体也是有价值的工具，特别是在免疫学研究中。这里我们描述了一项原理验证研究，涉及一种新的水溶性香豆素探针，该探针具有马来酰亚胺巯基反应单元，用于荧光标记生物分子。重点包括：（1）N-取代马来酰亚胺的便捷水基制备，（2）活化马来酰亚胺酯的一锅法制备，以及（3）硒醇促进的本征二硫键还原和无显著活性损失的抗体“位点特异性”标记的生物偶联方案。
• PROBE FOR iFRET AND USE THEREOF
  申请人：Chung Sang Jeon

  公开号：US20140242606A1

  公开（公告）日：2014-08-28

  The present invention relates to a probe for iFRET and use thereof. Specifically, the present invention relates to a novel probe for iFRET, a method for preparing the probe for iFRET, a method for searching a target protein-specific binding site or a molecule having the binding site using the probe for iFRET, and a method for imaging the target protein using the probe for iFRET. The probe for iFRET according to the present invention utilizes an amino acid in a protein as a fluorescent donor, unlike the conventional FRET method. Therefore, only one fluorescent material is used, and its emission wavelength is distinct from the intrinsic fluorescence of the protein. Thus, high specificity and sensitivity are ensured, and the quantity, activity and mechanism of various proteins can be analyzed in an easy and accurate manner.

  本发明涉及一种用于iFRET的探针及其使用。具体而言，本发明涉及一种新型iFRET探针、制备iFRET探针的方法、使用iFRET探针搜索靶蛋白特异性结合位点或具有结合位点的分子的方法，以及使用iFRET探针成像靶蛋白的方法。本发明的iFRET探针利用蛋白质中的氨基酸作为荧光给体，而不是传统的FRET方法。因此，仅使用一个荧光材料，其发射波长与蛋白质的内在荧光不同。因此，确保了高度的特异性和灵敏度，并且可以轻松准确地分析各种蛋白质的数量、活性和机制。
• WO2020127602A5
  申请人：——

  公开号：WO2020127602A5

  公开（公告）日：2022-12-20
• Dey, Journal of the Chemical Society, 1915, vol. 107, p. 1637
  作者：Dey

  DOI：——

  日期：——
• First Total Synthesis of a Fluorescent Didemnin
  作者：Padma Portonovo、Xiaobin Ding、Michael S. Leonard、Madeleine M. Joullié

  DOI：10.1016/s0040-4020(00)00287-8

  日期：2000.6

  A dimethylaminocoumarin fluorophore was linked to didemnin A through a glycine tether. The resultant fluorescent didemnin will be used to study cellular localization as detected by fluorescence microscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.