7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin | 876275-37-5

• 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: 7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin
• 英文别名: 2-[Carboxymethyl-[4-(hydroxymethyl)-2-oxochromen-7-yl]amino]acetic acid
• CAS: 876275-37-5
• 化学式: C₁₄H₁₃NO₇
• 分子量: 307.26
• InChiKey: HLWQISZUESBNOD-UHFFFAOYSA-N

物化性质

• 沸点：
  706.4±60.0 °C(Predicted)
• 密度：
  1.584±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin 、 N,N-二甲基乙二胺 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以65%的产率得到7-[bis[2-[[2-(dimethylamino)ethyl]amino]-2-oxoethyl]amino]-4-(hydroxymethyl)coumarin trihydrochloride
  参考文献：
  名称：

  Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs

  摘要：

  A novel coumarin-based highly water-soluble photocleavable protective group was designed and synthesized, and then this photosensitive protecting group was used to design paclitaxel prodrugs. These novel paclitaxel conjugates demonstrated excellent water solubility, over 100 mg mL(-1). Thus, the use of a detergent in the formulation can be omitted completely, even at high doses. Phototaxel 11 released the parent drug, paclitaxel, quickly and efficiently by minimal tissue-damaging 365 nm UV light irradiation at low power, while laser activation at 355 nm led to extensive decomposition of the prodrug. The carbamate-type prodrug, phototaxel 11, was stable in the dark prior to activation, whereas carbonate-type phototaxel 9 demonstrated poor stability under aqueous conditions. For such prodrugs, tumor-tissue targeting after administration could be achieved by selective light delivery, similar to that used in photodynamic therapy. In addition, newly designed coumarin derivative 8 can be applied in organic chemistry as a photosensitive protective group and for the design of caged compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.022
• 作为产物：
  描述：

  di-tert-butyl 2,2'-((4-formyl-2-oxo-2H-chromen-7-yl)azanediyl)diacetate 在 甲醇 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin
  参考文献：
  名称：

  笼养的内源转录因子抑制剂的光解释放能够实现对CREB介导的基因表达的光化学控制。

  摘要：

  已经开发了一种直接的光化学方法，用于调节基因功能，该方法是通过对无活性的笼状前体进行解囊来开发的，该前体的片段化后会产生CREB（cAMP-反应元件结合蛋白）抑制剂，该抑制剂与负责调节CREB介导的基因表达水平的内源性转录因子结合。

  DOI：

  10.1021/acs.orglett.9b03568

文献信息

• Synthesis and Photocleavage of 7-[{Bis(carboxymethyl)amino}coumarin-4-yl]methyl-Caged Neurotransmitters
  作者：Naoko Senda、Atsuya Momotake、Tatsuo Arai

  DOI：10.1246/bcsj.80.2384

  日期：2007.12.15

  7-[Bis(carboxymethyl)amino}coumarin-4-yl]methyl-caged neurotransmitters (glutamate and GABA) were synthesized. Both caged compounds showed sufficient stability in the dark, were water-soluble at pH 7.2 without using organic solvents, and exhibited relatively high quantum yield for photolysis upon irradiation with 390 nm light.

  合成了7-[双(羧甲基)氨基]香豆素-4-基}甲基笼型神经递质（谷氨酸和GABA）。这两种笼型化合物在暗处具有足够的稳定性，在pH 7.2的水溶液中可溶，无需使用有机溶剂，并且在受到390 nm光照时展现出相对较高的光解量子产率。
• {7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl Derivatives for Photorelease of Carboxylic Acids, Alcohols/Phenols, Thioalcohols/Thiophenols, and Amines
  作者：Volker Hagen、Brigitte Dekowski、Nico Kotzur、Ralf Lechler、Burkhard Wiesner、Benoît Briand、Michael Beyermann

  DOI：10.1002/chem.200701142

  日期：2008.2.8

  series of 7-[bis(carboxymethyl)amino]coumarin-4-yl}methyl carboxylates, carbonates, carbamates, and thiocarbonates as potential phototriggers for compounds with COOH, OH, NH(2), and SH functions. The compounds are soluble in aqueous buffer, show low fluorescence, and are efficiently photolysed by irradiation with UV/Vis or IR light to release carboxylates, alcohols, phenols, amines, thioalcohols, or thiophenols

  光诱导的从无活性前体分子释放生物分子代表了一种研究具有高时间和空间分辨率的细胞过程的有力方法。在这里我们报告一系列7- [双（羧甲基）氨基]香豆素-4-基}甲基羧酸盐，碳酸盐，氨基甲酸酯和硫代碳酸盐的合成和光化学，作为潜在的光引发剂，用于与COOH，OH，NH（2）的化合物和SH函数。该化合物可溶于水性缓冲液，显示低荧光，并通过用UV / Vis或IR光照射而有效地光解，以释放出羧酸盐，醇，酚，胺，硫醇或硫酚。
• Wavelength-Selective Photoactivatable Protecting Groups for Thiols
  作者：Nico Kotzur、Benoît Briand、Michael Beyermann、Volker Hagen

  DOI：10.1021/ja907287n

  日期：2009.11.25

  water-soluble photolabile protecting groups for thiols based on 2-nitrobenzyl and (coumarin-4-yl)methyl chromophores, among them two new ones. The protecting groups allow, due to their different absorption maxima, wavelength-selective photocleavage of binary mixtures of cysteine derivatives protected at the thiol function with various photolabile protecting groups by irradiation with light. The concept

  我们开发并表征了基于 2-硝基苄基和 (香豆素-4-基) 甲基发色团的硫醇的高效、显着水溶性光不稳定保护基团，其中有两个新的。由于其不同的吸收最大值，保护基团允许在硫醇官能团处保护的半胱氨酸衍生物的二元混合物通过光照射进行波长选择性光裂解。该概念也适用于模型肽反应衍生物中两个不同的 S 保护的半胱氨酸残基。肽 Ac(0)-Cys(1)(BCMACMOC),Cys(8)(7,8BCMCMOC)-resact 和 Ac(0)-Cys(1)(C4MNB),Cys(8) 可以实现选择性光解(BCMACMOC)-通过分别用 > 或 = 402 nm 或 > 或 = 436 nm 波长的光照射发生反应，然后在 λ 下照射 >
• Wavelength-Selective Uncaging of Two Different Photoresponsive Groups on One Effector Molecule for Light-Controlled Activation and Deactivation
  作者：Isam Elamri、Chahinez Abdellaoui、Jasleen Kaur Bains、Katharina Felicitas Hohmann、Santosh Lakshmi Gande、Elke Stirnal、Josef Wachtveitl、Harald Schwalbe

  DOI：10.1021/jacs.1c02817

  日期：2021.7.21

  suppress its induced effect. The moiety resembling the tyrosyl side chain of the translation inhibitor puromycin was synthetically modified to the photosensitive ortho-nitrophenylalanine that cyclizes upon near UV-irradiation to an inactive puromycin cinnoline derivative. Additionally, the modified puromycin analog was protected by the thio-coumarylmethyl group as the second PPG. This TPOM strategy allows

  光可裂解保护基团 (PPG) 在众多研究中发挥着关键作用。它们能够控制释放小效应分子以诱导生化功能。近年来，附着在各种效应分子上的 PPG 数量迅速增长，满足了对新应用的高需求。然而，迄今为止，携带 PPG 的分子被设计为仅在一个方向上激活功能，即效应分子的释放。在此，我们提出了一种新方法双 PPG 单分子 (TPOM)，该方法利用两个光保护基团的正交光解首先释放效应分子，然后对其进行修饰以抑制其诱导效应。类似于翻译抑制剂嘌呤霉素酪氨酰侧链的部分被合成修饰为光敏邻硝基苯丙氨酸在近紫外线照射下环化为无活性的嘌呤霉素肉啉衍生物。此外，修饰的嘌呤霉素类似物受到硫代保护-香豆基甲基作为第二个PPG。这种 TPOM 策略允许初始波长选择性激活，然后是第二次光诱导失活。两种光解过程都在紫外/可见光和红外区域进行了光谱研究。结合量子化学计算和时间分辨核磁共振光谱，表征了照射后激活和失活步骤的光产物。我们
• Coumarinylmethyl Esters for Ultrafast Release of High Concentrations of Cyclic Nucleotides upon One- and Two-Photon Photolysis
  作者：Volker Hagen、Brigitte Dekowski、Vasilica Nache、Reinhard Schmidt、Daniel Geißler、Dorothea Lorenz、Jenny Eichhorst、Sandro Keller、Hiroshi Kaneko、Klaus Benndorf、Burkhard Wiesner

  DOI：10.1002/anie.200502411

  日期：2005.12.9